ORGANIC REACTION MECHANISMS-IV

CONTENTS
Particular Page No.

Theory 01 –06
Exercise - 1 07 – 11
Part - I : Subjective Questions
Part - II : Only One Option Correct Type
Part - III : Match the Columns
Exercise - 2 12 – 17
Part - I : Only One Option Correct Type
Part - II : Single or Double Digit Integer Type Questions
Part - III : One or More Than One Options Correct Type
Part - IV : Comprehensions
Exercise - 3 18 – 22
Part - I : JEE(ADVANCED) / IIT-JEE Problems (Previous Years)
Part - II : JEE(MAIN) / AIEEE Problems (Previous Years)
Answers 23 – 24

Additional Problems for Self Practice (APSP) 25 – 37

Part - I : PRACTICE TEST-1 (IIT-JEE (MAIN Pattern))
Part - II : NATIONAL STANDARD EXAMINATION IN CHEMISTRY (NSEC) STAGE-I
Part - III : PRACTICE TEST-2 (IIT-JEE (ADVANCED Pattern))
APSP Answers 38
APSP Solutions 38 – 42

JEE (Advanced) Syllabus

Alkyl Halide : Nucleophilic substitution reactions of alkyl halides; Rearrangement reactions of alkyl
carbocation, Preparation of alkenes and alkynes by elimination reactions.
Haloarenes : Nucleophilic aromatic substitution in haloarenes and substituted haloarenes (excluding
Benzyne mechanism and Cine substitution).
Alcohols: Esterification, dehydration, reaction with sodium, phosphorus halides, ZnCl2/concentrated HCl.
Ethers : Preparation by Williamson’s Synthesis.

JEE(Main) SYLLABUS
Organic Reaction Mechanisms : Organic Compounds with functional groups Containing
Halogens (x):
Alkyl halides : Nature of C-X bond in haloalkanes, physical and chemical properties, mechanism of
substitution reactions, elimination reactions and rearrangement reactions , reactivity of C-X bond in
haloalkanes.
Some commercially important compounds : Dichloro, trichloro and tetrachloromethanes; freons, BHC,
DDT, their uses and important reactions.
Organic compounds with functional groups containing oxygen
Alcohols & Ethers : Methods of preparation, physical and chemical properties;
Electronic structure, Structure of functional group, some commercially important compounds.

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Organic Reaction Mechanisms-IV

Elimination reactions:
In an elimination reaction two atoms or groups (YZ) are removed from the substrate and generally
resulting into formation of  bond.
| |
Elimination
 C  C   
 YZ
| |
Y Z
-elimination : When two groups are lost from the same carbon atom to give a carbene (or nitrene).
This is also called 1,1-elimination.



-elimination : When two groups are lost from adjacent atoms so that a new  bond is formed. This is
also called 1,2-elimination.



–elimination : It is also called 1,3-elimination, In this a three membered ring is formed.



Type of -elimination reactions : There are three types of elimination reactions

(I) E1 (II) E2 (III) E1cB

Section (A) : Unimolecular eliminaiton reaction (E1)

Proton and leaving group depart in two different step.
(a) First step : Slow step involves ionisation to form carbocation
(b) Second step : Abstraction of proton

(1) E1 Reaction of Alkyl halides :

Mechanism :

Step-1 :

Step-2 : + B –H

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Characteristics of E1 reaction :
(i) It is unimolecular, two step process.
(ii) It is a first order reaction.
(iii) Reaction intermediate is carbocation, so rearrangment is possible
(iv) In the second step, a base abstracts a proton from the carbon atom adjacent to the carbocation,
and forms alkene.
Rate of E1 = 3º Alcohol > 2º Alcohol > 1º Alcohol.
Rate of reaction  stability of carbocation
(v) Kinetics  Rate  [Alkyl halide]
Rate = k [Alkyl halide]
(vi) Energetics  The free energy diagram for the E1 reaction is similar to that for the SN1 reaction.

CH3
|
e.g. CH3  CH2  C  CH3  +
|
Br

e.g. 

(2) E1 Reaction of Alcohols :

Dehydration requires an acidic catalyst to protonate the hydroxyl group of the alcohol and convert it to a
good leaving group. Loss of water, followed by loss of proton, gives the alkene. An equilibrium is
established between reactants and products. For E1 mechanism reagents are :
(i) H3 PO4/ 
(ii) H2SO4 / 160º
| | | |
 C  C  acid
  C  C  + H2O (Rearrangement may occur)
| |
H OH

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Organic Reaction Mechanisms-IV
Mechanism :

Step-1 :

Step-2 : +

Step-3 : +

Remarks :
In first step, an acid-base reaction a proton is rapidly transferred from the acid to one of the unshared
electon pairs of the alcohol.
In second step the carbon oxygen bond breaks. The leaving group is water molecule.
Finally, in third step the carbocation transfers a proton to a molecule of water. The result is the
formation of a hydronium ion and an alkene.
Reactivity of ROH : 3° > 2° > 1°

e.g.

CH2OH CH2

Conc.H2SO 4
e.g.   +

(I)
Minor

Migration
H 
 of bond H
e.g.   


(3) E1 Reaction of Ether :

Elimination is not a favourable reaction for ether, but however few reactions have been observed.
E1 Elimination takes place via formation of stable carbocation.
Ether undergoes dehydration reaction in the presence of conc. H2SO4 /  

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Organic Reaction Mechanisms-IV

Conc. H2SO 4 / 
e.g.  

Section (B) : Bimolecular elimination reaction (E2)

(1) E2 Reaction of Alkyl halide :
Dehydrohalogenation is the elimination of a hydrogen and a halogen from an alkyl halide to form an
alkene. Dehydrohalogenation can take place by E1 and E2 mechanism.
Reagent
– – +
(i) Hot alcoholic solution of KOH or EtO / EtOH (ii) NaNH2 (iii) t-BuO K in t-BuOH

Mechanism :   + BH

Characteristics of E2 reaction 
1. This is a single step, bimolecular reaction
2. It is a second order reaction
3. Kinetics  Rate  [R – X] [Base]
Rate = k [R – X] [ ]
4. Rearrangment is not possible
5. For the lower energy of activation, transition state must be stable
6. E2 follows a concerted mechanism
7. The orientation of proton & leaving group should be antiperiplanar.
8. Here –H is eliminated by base hence called  elimination
9. Positional orientation of elimination  In most E1 and E2 eliminations where there are two or more
possible elimination products, the product with the most highly substituted double bond will
predominate. This rule is called the saytzeff or zaitsev rule.
Reactivity towards E2  R–I > R–Br > R–Cl > R–F
Rate of E2 reaction = 3º Alkylhalide > 2º Alkylhalide > 1º Alkylhalide
For example : Dehydrohalogenation of 2-bromo-2-methylbutane can yield two products.

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Organic Reaction Mechanisms-IV

TS-2

TS-1

Formation of the Hoffmann product

Bulky bases can also accomplish dehydrohalogenations that do not follow the Saytzeff rule. Due to
steric hindrance, a bulky base abstracts a less hindered proton, often the one that leads to formation of
the least highly substituted product, called the Hofmann product.
H CH3
| |
CH3  C  C  CH2
| | | +
H Br H

+
Hofmann product

Bulky base :

(CH3CH2)3N:

Triethylamine
Stereospecific E2 reactions
The E2 is stereospecific because it normally goes through an anti periplanar transition state. The
products are alkenes.
Ph Ph Base
H

Ph H CH3
Ph H
  = = Ph Ph
H CH3 CH3 Ph
CH3 Ph H
Br H
Br

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Organic Reaction Mechanisms-IV

Ex-1. +

Ex-2. +

Ex-3.

t BuO  –
Ex-4.  +


Section (C) : Unimolecular elimination by conjugate base (E1cB) 

In the E1 cB, H leaves first and then the X. This is a two step process, the intermediate is a carbanion.

Mechanism :
H
| |
CC X
Step-1 : (conjugate base)
| |

Step-2 :  – C  C –
| |

Remarks :
First step consists of the removal of a proton ( ) by a base generating a carbanion.
In second step carbanion looses a leaving group to form alkene.
Condition: For the E1cB, (i) substrate must be containing acidic hydrogens and (ii) poor leaving
groups.

e.g.  

e.g. X2C = CF2

e.g. R2C = O +

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Organic Reaction Mechanisms-IV

 Marked Questions may have for Revision Questions.

PART - I : SUBJECTIVE QUESTIONS

Section (A) : Unimolecular eliminaiton reaction (E1)
A-1. Why dehydration of alcohol takes place in acidic medium generally but not in basic medium.
A-2. 1º alcohols are poor starting material for synthesis of 1-Alkene. Explain ?
A-3. Predict the major product of the acid catalysed dehydration of the following alcohols :
(a) (CH3)2C(OH)CH2CH3 (b) CH3CH2 CH2CH(OH)CH3
(c) (CH3)2C(OH)CH(CH3)2 (d) (CH3)3CCH2OH
A-4. When 1-Bromo-1-methylcyclohexane is heated in ethanol for an extended period of time, three
products result: one ether and two alkenes. Predict the products of this reaction, and propose a
mechanism for their formation. Also, mention the major elimination product.
Section (B) : Bimolecular elimination reaction (E2)
B-1. A halide with formula C6H13I is found to give two isomeric alkenes 2-methyl-2-pentene and 4-methyl-2-
pentene on dehydrohalogenation with alcoholic KOH. Suggest its structure.

B-2.

Explain why more alkylated alkene is formed predominatly if base is , while less alkylated
alkene is obtained majorly when base is used.
B-3. Bromocyclodecane on heating with ethanolic KOH, produces two alkenes. Write the two products also
mention the major one.
B-4. Which alkyl chloride would yield following pure alkene on reaction with alcoholic KOH ?
CH3
|
(i) CH3  C  CH2 (ii) CH3–CH2–CH2–CH=CH2 (iii) CH3  CH2  C  CH2
|
CH3

B-5. Predict all the alkenes that would be formed by dehydrohalogenation of the following alkyl halides with
sodium ethoxide in ethanol and identify the major alkene :
(i) 1-Bromo-1-methylcyclohexane (ii) 2-Chloro-2-methylbutane

(iii) 2, 2, 3-Trimethyl-3-bromopentane. (iii)  >

B-6. Give the major products of following reaction :

(a) ? (b) ?

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Organic Reaction Mechanisms-IV
Section (C) : Unimolecular elimination by conjugate base (E1cB)
C-1. What are the essential conditions for any reaction to show E1cB mechanism ?
C-2. If ethanol containing EtOD is used as solvent, then deuterium exchange take place in E1cB
mechanism. Why ?
C-3. If the mechanism is E1cB then the possible products will be :
MeO
?

MeOD

PART - II : ONLY ONE OPTION CORRECT TYPE

Section (A) : Unimolecular eliminaiton reaction (E1)
A-1. Which of the following reaction is an example of elimination reaction :
CH MgBr
(A) CH3–CHO 
3
 CH3  CH  CH3
H2O
|
OH
Conc. H2SO 4
(B) CH3  CH  CH3   CH3–CH=CH2
| 
OH
PBr3
(C) CH3–CH2–OH   CH3–CH2–Br
NaNH2
(D) CH3–CH2–COOH   CH3 –CH2–COONa + NH3
A-2. Correct statement for E1 Reaction is :
(A) It is a two step process. (B) Rearrangement is possible.
(C) Good leaving group favours (D) All of these
A-3. Intermediate formed during E1 reaction is –
(A) Carbocation (B) Carbanion (C) Free radical (D) Carbene
EtOH / 
A-4. CH3–CH–CH–CH3  Major elimination product X.
CH3 Cl
X is %
CH3 CH3 C2H5 CH3CH3
(A) CH3–CH–CH=CH2 (B) CH3–C=CH–CH3 (C) CH3–C=CH2 (D) CH3–C C–CH3

Conc. H SO
A-5. 
2 4
 Major Product


Major product is :

(A) (B) (C) (D)

Conc. H SO
A-6. In the given reaction : 2 4
  [X] as major product

[X] will be :

(A) (B) (C) (D)

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Organic Reaction Mechanisms-IV
A-7. Identify the major product formed in the following reaction
H 3C C 6H 5
2 4 H SO / 
H3C–C—C–C6H5 
HO OH
CH3 C6H5
(A) CH3–C— C–C6H5 (B) CH3–C–C–C6H5
C 6H 5 O O CH3
H 3C C 6H 5
(C) CH2=C—C–C6H5 (D) CH3–C C–C6H5
OH CH3 C6H5

A-8. Which of the following does not representing the correct product

(A) (B)

(C) (D)

Section (B) : Bimolecular elimination reaction (E2)

B-1. Correct statement for E2 Reaction is :
(A) It is a two step process. (B) It is an unimolecular reaction
(C) Strong base favours (D) Carbanion is formed during the reaction

B-2. Intermediate of E2 reaction is –

(A) Carbocation (B) Carbanion
(C) Free radical (D) Intermediate is not Formed

CH3
Alc.KOH
B-3. CH3–C–CH2Br  Alkene ,

H
Alkene is –

(A) (B) (C) (D)

B-4. Which of the following cannot undergo E2 reaction ?

(A) (B) (C) (D)

B-5. 2-Chlorobutane on treatment with alcoholic KOH/ gives major product :

(A) 2-Butene (B) 1-Butene (C) 2-Butanol (D) 1-Butyne

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Organic Reaction Mechanisms-IV

B-6. Major Product is :

OH
(A) CH 3–C=CH–CH 3 (B) CH 3–CH–CH=CH 2 (C) CH 2=C–CH 2–CH 3 (D) CH3–CH–CH–CH3
CH 3 CH3 CH3 CH3

B-7.

X and Y are respectively :

(A) and

(B) and

(C) Both

(D) Both

B-8. Identify the major products in the following reaction ?

CH3
—


OH/ 
CH3—CH2—N—CH2—CH2—CH3  
—

CH3

(A) CH3–CH=CH2 (B) CH2= CH2 (C) (D) C2H5–OH

Section (C) : Unimolecular elimination by conjugate base (E1cB)

C-1. Reaction intermediate of E1cB reaction is :
(A) Carbocation (B) Carbanion (C) Benzyne (D) Free radical
C-2. D-exchange is observed in :
(A) E1 (B) E2 (C) E1cB (D) none of these

C-3. Major Product is :

(A) (B) (C) (D)

C-4. Major product of given reaction is-

OH
O2N–CH2–CH–CH3   Major product

Cl
(A) O2N–CH=CH–CH3 (B) O2N–CH2–CH=CH2 (C) O2N–CH=C–CH3 (D) CH2  C  CH3
|
Cl NO2

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Organic Reaction Mechanisms-IV

PART - III : MATCH THE COLUMN

1. Match List I (Reaction) with List II (Type of reaction) and select the correct answer using the code given

below the lists :

List I List II

(P) (1) SN1

(Q) Alc. KOH (2) SN2




(R) H SO (3) E1
2 4
 


(S) (4) E2
H O
2


Codes :
P Q R S P Q R S
(A) 4 2 1 3 (B) 2 4 3 1
(C) 3 1 2 4 (D) 2 1 4 3

2. Match reactions written in List-I with their mechanism in List-II.

List-I List-II

Ph–CH2–CH2– Br + Ph–CH=CH2
(A) (p) SN1

(B) Ph–CH2–CH2–Br Ph–CH2–CH2–OEt + Ph–CH=CH2 (q) SN2

(C) Ph–CH2–CH2–Br Ph–CH=CH2 (r) E1

(D) Ph–CH2–CH2–Br Ph–CH=CH2 + Ph–CD2–CH2Br (s) E2

(t) E1cB

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 Marked Questions may have for Revision Questions.

PART - I : ONLY ONE OPTION CORRECT TYPE

1. The relative rate of acid catalysed dehydration of following alcohols would be :

CH3
|
C – Ph
|
OH
IV
(A) III > I > IV > II (B) III >IV > I > II (C) I > III > IV > II (D) IV > III > I > II
2. Which one of the following compound undergoes E1 reaction most readily ?
CH3
(A) CH3–C–CH2–CH3 (B) CH3–CH2–CH2–Br
Br
CH3
(C) CH3–CH2–CH2–I (D) CH3–C–CH2–CH3
I

CH3OH
3. In the given reaction,   [X]


[X] as the major product among the elimination products is :

CH3
|
(A) C = CH2 (B) (C) (D)

Cl
aq. Acetone Conc. H3PO4,
4. Product
Step-1 Step-2
Intermediates for both the steps are respectively ?
(A) Carbocation & No intermediate (B) No intermediate & carbocation
(C) Carbocation & carbanion (D) Carbocation & carbocation
5. Arrange the following in decreasing order of stability of their transition state during elimination by strong
base

(A) II > I > III (B) II > III > I (C) I > III > II (D) I > II > III

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Organic Reaction Mechanisms-IV
6. Which of the following will undergo fastest elimination reaction with alcoholic KOH.

(A) (B) (C) (D)

7. (a) X (b) Y

Identify the product of the following elimination reaction X and Y respectively with stereochemistry :
Ph CH3 H 3C Ph Ph Ph H3C CH3
(A) C=C C=C (B) C=C C=C
H Ph H CH3 H CH3 H Ph
cis cis
Ph CH3 H3C CH3 Ph Ph H3C Ph
(C) C=C C=C (D) C=C C=C
H Ph H Ph H CH3 H CH3
trans cis cis trans

8. Which mechanism has different reactivity order of alkyl halides (1º, 2º, 3º) than others :
(A) SN1 (B) SN2 (C) E1 (D) E2
9. The correct order of SN2 / E2 ratio for the % yield of product of the following halide is :

(P) (Q)

(R) CH3 – CH2 – I (S)

(A) R > S > Q > P (B) R > Q > S > P (C) P > R > S > Q (D) Q > P > R > S

(1) NaOH (2) PBr

(3) KOH (4) SOCl
10.   
3
  
2
 (II) Product
(Aprotic solvent) DMSO

In this reaction I and II are,

(A) Enantiomers (B) Structure isomers
(C) Geometrical isomers (D) Identical compounds
11. Select the incorrect option for the following statements.
(A) Bimolecular elimination of alkyl halides is a stereospecific reaction.
(B) In SN2 reaction a single isomer is the only product.
(C) Alcohol dehydrate in strongly basic conditions by E1 mechanism.
(D) 3-hydroxypropanal dehydrates in strong basic condition by E1cb mechanism.
12. Predict the possible number of alkenes and the main alkene in the following reaction.

Product

(A) 2 and (B) 2 and

(C) 4 and H2C=CH2 (D) 3 and H2C=CH2

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PART - II : SINGLE AND DOUBLE VALUE INTEGER TYPE

1. ‘X’ is a smallest optically active alkanol. On dehydration it can form Y number of alkenes (including
stereoisomers). On reaction with Lucas reagent it forms Z number of alkyl halides (including
stereoisomers). Report your answer as Z Y .

2. If the starting material is labelled with deuterium as indicated, predict how many total deuterium atoms
will be present in the major elimination product ?
HO CD3 HO CH3
D D

(a) Conc. H SO

2 4
 (b) D D 
Conc. H2SO4

 

3. The total number of alkenes possible by dehydrobromination of 3-bromo-3-methylhexane using

alcoholic KOH is :
OH
conc.H SO
4. In the given reaction : CH3–CH–CH–CH3 
2 4
 Alkenes

Ph
Total number of alkenes (Including stereo isomers) formed will be

Alc. KOH
5.   Alkenes

the total number of possible alkenes in this elimination reaction is.
6. The difference of molecular weights of the major products P and Q form at the followng reactions is
OH
KOH/
(i) + CH3I   P (organic product)
CH3
I
KOH/
(ii) + CH3CH2OH   Q (organic product)
CH3
7. Rearrangement of carbon skeleton of substrate is possible in which of the following reactions ?
SN1, SN2, E1, E2, E1cB, SN2Th, SN2Ar, EAS (Electrophilic aromatic substitution), electrophilic addition
on alkenes, free radical substitution of alkanes.
8. Observe the following reaction sequence
OH OH
Ph 
Conc. H2SO4 , (boil) LiAlH4
 (G) 
H3PO4 , 
 (H)   (I)
Ph (1) (2) (3)

Calculate molecular mass [W] of product I and report your answer as N , where N = W  3.

PART - III : ONE OR MORE THAN ONE OPTIONS CORRECT TYPE

1. Predict the products expected in given reaction
2 5 C H OH
2-Bromo-1,1-dimethylcycopentane  


(A) (B) (C) (D)

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2. Which of the following order is/are correct for the rate of E2 reaction ?
(A) 5-Bromocycloheptene > 4-Bromocycloheptene
(B) 2-Bromo-1-phenylbutane > 3-Bromo-1-phenylbutane
(C) 3-Bromocyclohexene > Bromocyclohexane
(D) 3-Bromo-2-methylpentane > 2-Bromo-4-methylpentane
3. Which of the following statement (s) is/are true about the following eliminations ?
 
t BuO EtO
(I)   (II)  
DMSO 
(A) Hoffmann product is major product in I. (B) Saytzeff product is major product in I
(C) Hoffmann product is major product in II. (D) Saytzeff product is major product in II
4. In which reaction product formation takes place by Hoffmann rule ?

(A) CH3  CH2  CH  CH3 (B) CH3  CH2  CH  CH3

| |
Br F

(C) (D)

5. Which of the following compounds can give E1cB reaction ?

(A) CF3–CHCl2 (B) C6H5 – CH– CH2F (C) CH3–CH2–CH2Br (D) C6H5 – CH–CH2–CHO
NO2 OH
6. Which of the following statement (s) is/are correct
(A) E2 is a concerted reaction in which bonds break and new bonds form at the same time in a single
step.
(B) Order of reactivity of alkyl halides towards E2 dehydrohalogenation is found to be 3º > 2º > 1º
(C) In E2 reaction both  hydrogen and leaving group should be antiperiplanar.
(D) In E2 elimination different stereoisomer (diastereomer) converts into different stereo product.
7. Following graph between G and reaction progress in for/can be :

(A) SN1 reaction (B) E1 reaction

(C) Aromatic electrophilic substiution (D) Electrophilic addition reaction
8. Which observation/s will be correct about the major products X and Y of the following reaction.

(A) X is (B) X is (C) Y is (D) Y is

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9. In which of the following reaction, regioselectivity can be observed.
CH3 CH3
alc. KOH /  alc. KOH / 
(A) CH3–C–CH2–Cl  (B) CH3–C–CH3 
H Cl
CH3
alc. KOH /  alc. KOH / 
(C) CH3–C–CH2–CH3  (D) 
Cl

80% EtOH
10.  

What is / are true about above reaction ?

(A) Major product is given by SN1 reaction.
(B) Through E1 mechanism 3 alkenes are formed.
(C) 3-Methylpentan-3-ol is also formed as one of the product.
(D) Fractional distillation of elimination products will give two fractions.

PART - IV : COMPREHENSION
Read the following passage carefully and answer the questions.
Comprehension # 1
Alcohols undergo acid catalysed elimination reactions to produce alkenes. Because water is lost in the
elimination , this reaction is called dehydration reaction. Secondary and tertiary alcohols always give E1
reaction in dehydration. Primary alcohols whose -carbon is branched also give E1 reaction. The
reactivity of alcohol for elimination reaction is tertiary alcohol > Secondary alcohol > Primary alcohol.
1. Which of the following dehydration product (major) is incorrect ?

conc.H SO
(A) 
2 4



conc.H SO
(B) 
2 4



conc.H2SO4
(C) CH3CH2CH2CH2OH   CH3–CH=CH–CH3


conc.H SO
(D) 
2 4



2. Identify the product in the given reaction :

Product

(A) (B)

(C) (D)

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Comprehension # 2

3. The incorrect statement about step-1 is :

(A) It is SN2 reaction
(B) Only one transition state is formed in this reaction
(C) Walden inversion has occured at reactant ‘X’
(D) The reaction has molecularity two
4. The product ‘E’ is %
(A) CH3–CH2–CH=CH2 (B) CH3–CH=CH–CH3 (C) CH2=CH2 (D) CH3–CH=CH2
5. The product ‘F’ is :

(A) C2H5SH (B) (C) CH3SH (D)

Comprehension # 3
Answer Q.6, Q.7 and Q.8 by appropriately matching the information given in the three columns
of the following table.
Observe the three columns in which column-1 represents reactants, column-2 represents reaction conditions
while column-3 represents products.
Column-1 Column-2 Column-3

(I) (i) Zn dust /  (P)

HO OH
Cl Cl
(II) (ii) Conc. H2SO4 (Q)
Cl
OH
(III) (iii) HCl/ZnCl2 (R)

OH
(IV) (iv) Aqueous AgNO3 (S)
O

6._ The bimolecular reaction is represented by :

(A) (IV), (iii), (Q) (B) (I), (ii), (S) (C) (lll), (ii), (P) (D) (ll), (i), (R)
7._ The dehydration reaction is represented by :
(A) (lll), (ii), (R) (B) (lll), (iv), (P) (C) (l), (ii), (S) (D) (IV), (iii), (R)
8._ The unimolecular nucleophilic substitution is represented by :
(A) (ll), (iii), (Q) (B) (l) (iv), (S) (C) (IV), (iv), (Q) (D) (IV), (iii), (Q)
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PART - I : JEE (ADVANCED) / IIT-JEE PROBLEMS (PREVIOUS YEARS)

* Marked Questions may have more than one correct option.
1. Identify (X), (Y) and (Z) in the following synthetic scheme and write their structures. Explain the
formation of labelled formaldehyde (H2C*O) as one of the products when compound (Z) is treated with
HBr and subsequently ozonolysed. Mark the C* carbon in the entire scheme.
* 14
BaCO3 + H2SO4  (X) gas [C* denotes C ]
(i) Mg / ether 4 LiAlH
CH2=CH–Br   (Y)   (Z) [IIT-JEE 2001(M), 5/135]
(ii) X
(iii) H3 O

2. Identify the set of reagents/reaction conditions ‘X’ and ‘Y’ in the following set of transformations.
X Y
CH3–CH2–CH2Br   product  CH3  CH  CH3 [IIT-JEE 2002(S), 3/150]
|
Br
(A) X = concentrated alcoholic NaOH, 80°C; Y = HBr acetic acid, 20°C
(B) X = dil. aq. NaOH, 20°C, Y = HBr / acetic acid, 20°C
(C) X = dil. aq. NaOH, 20°C, Y = Br2 / CHCl3, 0°C
(D) X = conc. alc. NaOH, 80°C, Y = Br2 / CHCl3, 0°C

H  Br / CCI
3.  [F] 
2 4

–H2 O

How many structures of F is possible? [IIT-JEE 2003(S), 4/144]

(A) 2 (B) 5 (C) 6 (D) 3
4. Which is the best reagent to convert cyclohexanol into cyclohexene. [JEE-2005, 3/144]
(A) conc. HCl (B) conc. HBr (C) conc. H3PO4 (D) HCl + ZnCl2
5. Match the following (one term in column-I may match with more than one terms in column-II)
[JEE-2006, 6/184]
Column I Column II
(A) CH3 – CH – CD3 on reaction with C2H5O– gives CH2=CH–CD3 (p) The reaction is E1
|
Br
(B) PhCH2CH2Br gives elimination faster than PhCD2CH2Br. The (q) The reaction is E2
mechanism is
(C) PhCH2CH2Br in presence of C2H5OD/C2H5O– gives good (r) The reaction is E1 cB
yield of PhCD2CH2Br along with alkene
(D) CH3 – CH – CD3 and Ph – CH – CH3 on elimination, yield (s) The reaction is unimolecular
| |
Br Br
alkene at the same rate
Comprehension # 1
In the following reaction sequence, product I, J and L are formed. K represents a reagent.

Hex-3-ynal I J

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6. The structure of the product I is [IIT-JEE 2008, 4/162]

(A) (B)

(C) (D)

7. The structures of compound J and K, respectively, are [IIT-JEE 2008, 4/162]

(A) and SOCl2 (B) and SOCl2

(C) (D) and CH3SO2Cl

8. The structure of product L is [IIT-JEE 2008, 4/162]

(A) (B)

(C) (D)

9. The total number of alkenes possible by dehydrobromination of 3-bromo-3-cyclopentylhexane using

alcoholic KOH is [JEE-2011, 4/160]
Comprehension # 2
An acyclic hydrocarbon P, having molecular formula C6H10, gave acetone as the only organic product
through the following sequence of reactions, in which Q is an intermediate organic compound.

(i) Conc. H2SO4

(catalytic amount)
(i) dil. H2SO4 / HgSO4 (–H2O) O
P Q
(ii) NaBH4/ethanol (ii) O3
(C6 H10 ) (iii) dil. acid H3C CH3
(iii) Zn/H2O

10. The structure of compound P is [JEE 2011, 3/160]

(A) CH3CH2CH2CH2–CC–H (B) H3CH2C–CC–CH2CH3
(C) (D)

11. The structure of the compound Q is [JEE 2011, 3/160]

(A) (B)

(C) (D)

12. The major product (H) in the given reaction sequence is : [IIT-JEE 2012, 3/136]

CN 95% H2SO 4
CH3–CH2–CO–CH3   G  H
Heat
(A) (B)

(C) (D)

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13. Match the chemical conversions in List I with the appropriate reagents in List II and select the correct
answer using the code given below the lists : [IIT-JEE-2013, 3/120]
List I List II

P. Cl 1. (i) Hg(OAc)2 ; (ii) NaBH4

Q. ONa OEt 2. NaOEt

OH
R. 3. Et-Br

S. 4. (i) BH3 ; (ii) H2O2/NaOH

OH
Codes :
P Q R S P Q R S
(A) 2 3 1 4 (B) 3 2 1 4
(C) 2 3 4 1 (D) 3 2 4 1
Comprehension # 3
In the following reactions :
Pd-BaSO4 i. B2H6
C8H6 C8H8 X
H2 ii. H2O2, NaOH, H2O

H2O
HgSO4, H2SO4

i. EtMgBr, H2O
C8H8O Y
ii. H+, heat
14. Compound X is [IIT-JEE-2015, 4/168]
O OH

CH3 CH3
(A) (B)

OH
CHO
(C) (D)

15. The major compound Y is [IIT-JEE-2015, 4/168]

CH3 CH3
(A) (B)

CH3
CH2
CH3
CH3
(C) (D)

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16. The number of hydroxyl group(s) in Q is : [IIT-JEE-2015, 4/168]
H+
P Q
heat

PART - II : JEE (MAIN) / AIEEE PROBLEMS (PREVIOUS YEARS)

1. Maximum dehydration takes place that of : [AIEEE-2002, 3/225]

(1) (2) (3) (4)

2. During dehydration of alcohols to alkenes by heating with concentrated H2SO4 the initation step is
(1) Protonation of alcohol molecule (2) Formation of carbocation [AIEEE-2003, 3/225]
(3) Elimination of water (4) Formation of an ester
3. Among the following compounds which can be dehydrated very easily : [AIEEE-2004, 3/225]
H3C H3C

(1) (2)
OH H3C OH
CH3
OH

(3) (4)
H3C OH CH3 H3C CH3

4. Elimination of HBr from 2-bromobutane result in the formation of : [AIEEE-2005, 3/225]

(1) Predominantly 2-butyne (2) Predominantly 1-butene
(3) Predominantly 2-butene (4) Equimolar mixture of 1 and 2-butene
5. Reaction of trans 2-phenyl-1-bromocyclopentane on reaction with alcoholic KOH produces:
[AIEEE-2006, 3/165]
(1) 2-phenylcyclopentene (2) 1-phenylcyclopentene
(3) 3-phenylcyclopentene (4) 4-phenylcyclopentene

Base / 
6.  

The alkene formed as a major product in the above elimination reaction is : [AIEEE-2006, 3/165]

(1) (2) CH2=CH2 (3) (4)

conc. H2 SO4
7. The main product of the following reaction is, C6H5CH2CH(OH)CH(CH3)2  

(1) (2) [AIEEE-2010, 4/144]

(3) (4)

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8. Consider the following reaction: C2H5OH + H2SO4  Product
Among the following, which one cannot be formed as a product under any conditions ?
[JEE(Main) 2011, 4/120]
(1) Ethylene (2) Acetylene (3) Diethyl ether (4) Ethyl-hydrogen sulphate
LiAlH4 PCl5 Alc. KOH
9. In the reaction, CH3COOH   A   B   C,
the product C is : [JEE(Main) 2014, 4/120]
(1) Acetaldehyde (2) Acetylene (3) Ethylene (4) Acetyl chloride
10. 2-Chloro-2-methylpentane on reaction with sodium methoxide in methanol yields :
[JEE(Main) 2016, 4/120]
CH3
|
(a) C2H5 CH2C  OCH3 (b) C2H5 CH2C  CH2 (c) C2H5 CH  C  CH3
| | |
CH3 CH3 CH3
(1) (a) and (c) (2) (c) only (3) (a) and (b) (4) All of these
11. The major product obtained in the following reaction is : [JEE(Main) 2017, 4/120]
Br
H t
BuOK
C6H5  
C6H5 
(+)
(1) C6H5CH=CHC6H5 (2) (+)C6H5CH(OtBu)CH2C6H5
t
(3) (–)C6H5CH(O Bu)CH2C6H5 (4) (±)C6H5CH(OtBu)CH2C6H5
12. Which of the following, upon treatment with tert-BuONa followed by addition of bromine water, fails to
decolourize the colour of bromine ? [JEE(Main) 2017, 4/120]
C6H5 O
(1) (2)
Br Br
O
O
(3) (4)
Br Br

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EXERCISE – 1
PART - I
A-1. In basic condition very poor leaving group –OH will eliminate but in acidic medium –OH will be

converted into – OH2 which is very good leaving group.

A-2. 1º carbocation R – CH2 would rearrange and 2-alkene would result. Even if 1-alkene is also formed
but, it would tend to rearrange in acidic medium to 2-alkene.
CH3 CH3
CH3 CH3
A-3. (a) CH3 C CHCH3 (b) CH3–CH2–CH=CH–CH3 (c) C C (d) CH3 C CHCH3
CH3 CH3

A-4. +

B-1.

B-2. t- is bulky base so Hoffmann product is formed as major product.

B-3. +

B-4. (i) or ; (ii) CH3CH2CH2CH2CH2Cl ; (iii) CH CH CHCH Cl

3 2 2
|
CH3

B-5. (i) 
 > (ii) 
 >

(iii) 
 >

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B-6. (a) (b)

C-1. The compound must have acidic -hydrogen and a relatively poor leaving group.
C-2. In E1cB mechanism carbanion is formed as intermediate and 1st step is reversible.

C-3. CH=CH–CH3 + CH–CH–CH3

D Br
PART - II
A-1. (B) A-2. (D) A-3. (A) A-4. (B) A-5. (A)
A-6. (B) A-7. (B) A-8. (C) B-1. (C) B-2. (D)
B-3. (A) B-4. (C) B-5. (A) B-6. (B) B-7. (A)
B-8. (B) C-1. (B) C-2. (C) C-3. (B) C-4. (A)
PART - III
1. (B) 2. (A  p,r) ; (B  q,s) ; (C  s) ; (D  t)

EXERCISE – 2
PART - I
1. (D) 2. (D) 3. (C) 4. (D) 5. (A)
6. (A) 7. (C) 8. (B) 9. (A) 10. (C)
11. (C) 12. (C)
PART - II
1. 23 2. 6 3. 5 4. 5 5. 3
6. 32 [Molecular Weights (P – Q) = 114 – 82 = 32] 7. 3 8. 78
PART – III
1. (ABCD) 2. (BCD) 3. (AD) 4. (ABCD) 5. (ABD)
6. (ABCD) 7. (ABCD) 8. (BD) 9. (CD) 10. (ABC)
PART - IV
1. (B) 2. (C) 3. (C) 4. (A) 5. (C)
6. (D) 7. (C) 8. (D)

EXERCISE – 3
PART - I
* * *
1. (X) = CO2 ; (Y) = CH2  CH  C O  H ; (Z) = CH2  CH  CH2  OH  H2O 2. (A)
||
O
3. (D) 4. (C) 5. (A) - q ; (B) - q ; (C) - r, s ; (D) - p, s 6. (D)
7. (A) 8. (C) 9. 5 10. (D) 11. (B)
12. (A) 13. (A) 14. (C) 15. (D) 16. (4)
PART - II
1. (2) 2. (1) 3. (3) 4. (3) 5. (3)
6. (2) 7. (1) 8. (2) 9. (3) 10. (4)
11. (1) 12. (4)
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This Section is not meant for classroom discussion. It is being given to promote self-
study and self testing amongst the Resonance students.

PART - I : PRACTICE TEST-1 (IIT-JEE (MAIN Pattern))

Max. Time : 1 Hr. Max. Marks : 120
Important Instructions
1. The test is of 1 hour duration.
2. The Test Booklet consists of 30 questions. The maximum marks are 120.
3. Each question is allotted 4 (four) marks for correct response.
4. Candidates will be awarded marks as stated above in Instructions No. 3 for correct response of each
question. ¼ (one fourth) marks will be deducted for indicating incorrect response of each question. No
deduction from the total score will be made if no response is indicated for an item in the answer sheet.
5. There is only one correct response for each question. Filling up more than one response in any question
will be treated as wrong response and marks for wrong response will be deducted accordingly as per
instructions 4 above.

H3O H3PO4
1. + PhMgBr  A  B  C


C is :

(1) (2) (3) (4)

2. The correct increasing order of reactivity for following alkyl halides towards elimination reaction with
alcoholic KOH is :

(I) (II) (III)

(1) II > I > III (2) I > II > III (3) II > III > I (4) III > II > I

conc. H2SO4
3. In the given reaction :   [X] as major product

[X] will be :

(1) (2) (3) (4)

O OH
NaOH,
4.   (Product)
The major product of the above reaction is obtained by mechanism
(1) SN2 (2) E2 (3) E1cB (4) SN1

5. Select the incorrect option for the following statements.

(1) Bimolecular elimination of alkyl halides is a stereospecific reaction.
(2) In SN2 reaction a single isomer is the only product.
(3) Alcohol dehydrate in strongly basic conditions by E1 mechanism.
(4) 3-hydroxypropanal dehydrates in strong basic condition by E1cb mechanism.

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Conc. H SO
6. 
2 4
 Major product is :

(1) (2) (3) (4)

7. Which of the following conformations of meso 2,3-dibromobutane will give bromoalkene with alcoholic
KOH ?
(1) Gauche form (2) Anti form
(3) Partial eclipsed form (4) Fully eclipsed form
8. 2-Bromopentane is heated with potassium ethoxide in ethanol. The major product obtained is
(1) 2-Ethoxypentane (2) pent-1-ene (3) cis-pent-2-ene (4) trans-pent-2-ene

CrO / H H 1) CH MgBr 
9. 3
 P 
 3

 Q 

 R
2) H3O (major)
OH
R is :
(1) But-1-ene (2) 2-methylbut-1-ene (3) 2-methylbut-2-ene (4) 2-methyl propene

Ph Conc. HBr NaNH / NH (  )

10.   
2 3
Major product is :
OH
CH2
(1) Ph (2) Ph (3) Ph (4) Ph
NH 2
NH 2
11. The most probable product in the following reaction is :

C H O– K 
2 5



Trans

(1) (2) (3) (4)

12. P, Product P is :

(1) (2) (3) (4) None

13. Which statement is false for elimination reaction.

(1) -elimination is more common than  &  elimination
(2) In-elimination, formation of multiple bond occur.
(3) -elimination may be E1, E2 or E1cB.
(4) E1 & E2 requires presence of poor leaving group but E1cB requires presence of good leaving
group.

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14. Which of the following statement is correct regarding following reaction ?
t BuOH
+ t-BuO–K+   ?

(1) Major product is endocyclic alkene formed according to Saytzeff.

(2) Major product is exocyclic alkene formed according to Saytzeff.
(3) Major product is exocyclic alkene formed according to Hoffmann.
(4) Major product is endocyclic alkene formed according to Hoffmann.
15. Substrate that show E1 reaction

(1) CH3CH2I (2) (3) (4)

16. Which of the following compound will give three alkenes after dehydrohalogenation.
(1) CH3–CH2–CH2–CH2–Br (2)

(3) (4)

17. PhSO2CH2–CH2–OMe product + .

The product is :
(1) PhSO2CH=CH2 (2) CH2=CH–OMe (3) PhSO2CH2–CD2OMe (4) CD2=CH2
CH2 – OH
H SO / H
18. 
2 4
 A. The product A is :


CH2 – HSO4 CH2 CH3 CH3

(1) (2) (3) (4)

OH
19. Typical features of E2 involve :
(1) Two step reaction
(2) Second step is the rate determining step
(3) Anti-periplanar transition state
(4) Formation of a carbanion intermediate, stabilized by conjugation with a strong –M group
20. An alkyl chloride produces a single alkene on reaction with sodium ethoxide and ethanol. The alkene
further undergoes hydrogenation to yield-2-methylbutane. Identify the alkyl chloride from amongst the
following :
(1) ClCH2C(CH3)2CH3 (2) ClCH2CH2CH2CH3
(3) ClCH2CH(CH3)CH2CH3 (4) CH3C(Cl)(CH3)CH2CH3

21. Relative ease of dehydration of alcohol follows which general order

(1) 3º > 2º > 1º alc. (2) 1º > 2º > 3º alc (3) 2º > 3º > 1º alc (4) 3º > 1º > 2º alc

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22. Which of the following is the correct major product for given reaction ?

H SO

2 4
 Product


(1) (2) (3) (4)

23. Which of the following is a -elimination reaction ?

NaOH / 
(1) HO–CH2–CH2–Br 


(2) CHCl3 + KOH   CCl2
HO / 
(3) 

NaNH2
(4) CH2=CH–Cl   HCCH

24. Correct order of E2/SN2 ratio is :

P= Q= R = CH3–Br S = CH3–CH2–Br

(1) P > Q > S > R (2) P > Q > R > S (3) R > S > Q > P (4) P > S > Q > R
25. The product C of the following reaction sequence is :

HBr alc. KOH HBr

  A  B   C
R 2O2

(1) (2) (3) (4)

26. The major product of following reaction is

EtO– (1eq)



(1) (2) (3) (4)

27. What is the correct sequence of reagent/s for the following conversion
CH3  CH  CH3  CH –CH –CH –I
3 2 2
|
Br
alc. KOH
HI  aq. KOH H2SO4 HI
(1)   (2)     

alc. KOH HBr / R2O2 KI alc. KOH KI
HCl
(3)   
 (4)    

acetone acetone

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28. In which of the following reaction the single product formed is not the saytzeff’s product

H SO H SO
(1) 
2 4
 (2) 
2 4


alc. KOH alc. KOH

(3)  (4) 

29. In the following reaction the correct order of percentage of products X, Y and Z is
CH3 CH3 CH3 CH3 CH2 CH3 CH3 CH3
| | | | || | | |
alc. KOH
CH3  CH2  C  CH  CH3  CH3  CH  C  CH  CH3 + C2H5  C – CH  CH3 + C2H5  C  C  CH3
| (X) (Y) (Z)
Br
(1) X > Y > Z (2) Z > Y > X (3) Z > X > Y (4) Y > Z > X
30. The rate of elimination is fastest in
(1) Ph–CH2–CH2–F (2) Ph  C  CH2  CH2  F
||
O
(3) Ph–O–CH2–CH2–F (4) CH3–CH2–CH2–F

Practice Test-1 (IIT-JEE (Main Pattern))

OBJECTIVE RESPONSE SHEET (ORS)

Que. 1 2 3 4 5 6 7 8 9 10

Ans.

Que. 11 12 13 14 15 16 17 18 19 20

Ans.

Que. 21 22 23 24 25 26 27 28 29 30

Ans.

PART - II : NATIONAL STANDARD EXAMINATION IN CHEMISTRY (NSEC) STAGE-I

1. An alkyl bromide produces a single alkene when it reacts with sodium ethoxide and ethanol. This
alkene undergoes hydrogenation and produces 2-methylbutane. What is the identity of the
alkylbromide ? [NSEC-2000]
(A) 1-bromo-2-methylbutane (B) 1-bromobutane
(C) 1-bromo-2, 2-dimethylpropane (D) 2-bromo-2-methylbutane
2. Which of the following most readily undergoes E2 elimination with a strong base ? [NSEC-2000]
(A) 2-bromopentane (B) 2-bromo-2-methylbutane
(C) 1-bromo-2, 2-dimethylpropane (D) 2-bromo-3-methylbutane
3. An alkyl chloride produces a single alkene on reaction with sodium ethoxide and ethanol. The alkene
further undergoes hydrogenation to yield 2-methylbutane. Identify the alkyl chloride from amongst the
following : [NSEC-2001]
(A) CICH2CH(CH3)CH2CH3 (B) CICH2CH2CH2CH3
(C) CICHC(CH3)2CH3 (D) CH3C(CI)(CH3)CH2CH3

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4. On heating glycerol with conc. H2SO4, a compound obtained which has an unpleasant odour. This
compound is : [NSEC-2001, 2004]
(A) ethylene glycol (B) allyl alcohol (C) acrolein (D) glycerol sulphate
5. n-Propylbromide and ethanolic potassium hydroxide react to give : [NSEC-2001]
(A) propyne (B) propene (C) propane (D) propanol
6. The peroxide effect occurs by : [NSEC-2001]
(A) ionic mechanism (B) heterolytic fission of double bond
(C) homolytic fission of double bond (D) free radical mechanism
7. Acid catalysed dehydration of 2-pentanol would give [NSEC-2006]
(A) 1-pentene as a major product (B) cis 2-pentene as a major product
(C) trans-2-pentene as a major product (D) cis- and trans-2-pentene in equal amount.
8. The major product formed in the following reaction is : [NSEC-2007]

H SO

2 4
 Major product
Heat

(A) (B) (C) (D)

9. Arrange the following compounds in order of decreasing reactivity in the elimination (bimolecular)
reaction with C2H5ONa [NSEC-2007]

(i) (ii) (iii) (iv)

(A) II > I > III > IV (B) IV > III > I > II (C) III > I > II > IV (D) I > III > IV > II
10. Compound X on treatment with HI gives Y. Y on treatment with ethanolic KOH gives Z (an isomer of X).
Ozonolysis of Z (with H2O2 workup) gives a two-carbon carboxylic acid and four carbon ketone. Hence,
X is :
(A) 2-methyl-2-pentene (B) 4-methyl-1-pentene [NSEC-2009]
(C) 2, 3-dimethyl-2-butene (D) 3-methyl-1-pentene
11. The major product of the following reaction is : [NSEC-2009]

3(i) H PO , 150ºC
4


(ii) C6H5COOOH

(A) (B) (C) (D)

H3C CH3 H3C CH 3

LG
12.   [NSEC-2013]
O2N CH3 O 2N CH3
LG
The carbanion expels a leaving group LG to yield an alkene as shown above by
(A) E1cB mechanism (B) E1 mechanism
(C) E2 mechanism (D) Such a reaction does not take place

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13. The compound that is most reactive with alcoholic KOH is [NSEC-2014]
(A) CH2=CH–Br (B) CH3CH2Br (C) (CH3)2CH–Br (D) CH3COCH2CH2Br

14. Four processes are indicated below : [NSEC-2015]

(i)HBr / no peroxide (ii) alcoholic KOH, 
(I)  

(i) HI (ii) aqueous NaOH, 

(II)  

Br
(i) Mg, ether (ii) CH O (iii) H , H O
(III) 2 2


Br
(i) aq. KOH (ii) CH MgBr, ether (iii) H O 
(IV) 3 3
Br 

The processes that do not produce 1-methylcyclohexanol are

(A) II, IV (B) I, II (C) III, IV (D) I, III
15. n-Butylcyclohexane is formed through the following sequence of reactions.
PCl5 , 0ºC (i) NaNH2 (excess)
(i) NaNH2 C4H9
X   Y  
 Z 
(ii) C H l


(ii)H 2 5
(iii) H2 / Pt, , pressure

ln the above scheme of reactions, “X” is – [NSEC-2015]

(A) (B) (C) (D)

16. An alkyl halide (X) on reaction with ethanolic sodium hydroxide forms an alkene (Y) which on further
reaction with HBr gives the same alkyl halide. The alkene (Y) on reaction with HBr/peroxide followed by
reaction with Mg metal followed by reaction with HCN produces an aldehyde (Z). Z is : [NSEC-2016]
CHO CHO
CHO
(A) (B) CHO (C) (D)

17. Spodoptol, a sex attractant, produced by a female fall armyworm moth, can be prepared as follows. The
structure of Spodoptol is (pKa : terminal alkynes ~ 25, alcohols ~ 17) [NSEC-2016]
i. NaNH2 (excess)
ii. n-C4 H9Br (1eq)
iii. H2 /Lindlar cat
HO—CH2 (CH2 )7 C CH Spodoptol
H H
(A) n-C4H9–O–CH2–(CH2)7—HC=CH2 (B)
HO–CH2 –(CH2 )7 n-C 4H9
H n-C4 H9
(C) (D) HO–CH2–(CH2)12–CH3
HO–CH2 –(CH2 )7 H

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PART - III : PRACTICE TEST-2 (IIT-JEE (ADVANCED Pattern))

Max. Time : 1 Hr. Max. Marks : 66

Important Instructions
A. General %
1. The test is of 1 hour duration.
2. The Test Booklet consists of 22 questions. The maximum marks are 66.
B. Question Paper Format :
3. Each part consists of five sections.
4. Section 1 contains 8 multiple choice questions. Each question has four choices (A), (B), (C) and (D) out
of which ONE is correct.
5. Section 2 contains 6 multiple choice questions. Each question has four choices (A), (B), (C) and (D) out
of which ONE OR MORE THAN ONE are correct.
6. Section 3 contains 4 questions. The answer to each of the questions is a single-digit integer, ranging from
0 to 9 (both inclusive).
7. Section 4 contains 1 paragraphs each describing theory, experiment and data etc. 3 questions relate to
paragraph. Each question pertaining to a partcular passage should have only one correct answer among
the four given choices (A), (B), (C) and (D).
8. Section 5 contains 1 multiple choice questions. Question has two lists (list-1 : P, Q, R and S; List-2 : 1, 2,
3 and 4). The options for the correct match are provided as (A), (B), (C) and (D) out of which ONLY ONE
is correct.
C. Marking Scheme
9. For each question in Section 1, 4 and 5 you will be awarded 3 marks if you darken the bubble
corresponding to the correct answer and zero mark if no bubble is darkened. In all other cases, minus one
(–1) mark will be awarded.
10. For each question in Section 2, you will be awarded 3 marks. If you darken all the bubble(s)
corresponding to the correct answer(s) and zero mark. If no bubbles are darkened. No negative marks will
be answered for incorrect answer in this section.
11. For each question in Section 3, you will be awarded 3 marks if you darken only the bubble corresponding
to the correct answer and zero mark if no bubble is darkened. No negative marks will be awarded for
incorrect answer in this section.

SECTION-1 : (Only One option correct Type)

This section contains 8 multiple choice questions. Each questions has four choices (A), (B), (C)
and (D) out of which Only ONE option is correct.

1. Rate of Bimolecular elimination (E2) reaction for the following :

H
H

Base
Cl  Base
H 
(i)  (ii) 
E2 E2
Cl
(A) Same for both conformers (B) i > ii
(C) ii > i (D) Can’t say anything about rate of E-2 reaction
2. Which is incorrect about alkyl bromide having molecular formula C5H11Br
(A) One isomeric alkyl bromide undergoes E1 elimination at the fastest rate
(B) Only one is incapable of reacting by the E2 mechanism
(C) Only one isomer gives a single alkene on E2 elimination
(D) 2-Bromopentane gives the most complex mixture of alkenes on E2 elimination

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3. The compound 'X' is
O
||
H2SO4 HIO4
  [X]  

O
OH

(A) (B) (C) (D)

OH OH OH OH
OH
4. When the all-cis isomer of C6H6Cl6 (1, 2, 3, 4, 5, 6-Hexachlorocyclohexane) is heated with alc. KOH, the
most probable product is :

(A) (B) (C) (D)

CHD2MgI Conc.H2 SO 4
5. CH2O  
 X   Y
H3 O 
In the above reaction compound X & Y respectively will be
OH
|
(A) CHD  CH2  OH , CHO–CHO (B) CHD2–CH2–OH , CHO–CHO
(C) CHD2–CH2–OH, CD2=CH2 (D) CHD  CH2  OH , CD2=CH2
|
OH
6. Major product of the given reaction is :

(A) (B) (C) (D)

Conc. H SO / 60ºC
7. 
2 4
 The product is –

(A) (B) (C) (D)

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8. Which one of the following hexachlorocyclohexane is least reactive and which one is most reactive for
E2 reactions with a strong base for dehydrohalogenation.

(A) I least & II most (B) II least & I most (C) III least & I most (D) III least & II most

Section-2 : (One or More than one options correct Type)

This section contains 6 multipole choice questions. Each questions has four choices (A), (B),
(C) and (D) out of which ONE or MORE THAN ONE are correct.

9. In which of the following reactions the correct major products are mentioned

CH3
EtO
(A) 

Br
H3C CD3 H 3C CD3

EtO
(B) 

NaOEt
(C) EtOH

H SO , 
(D) 
2 4



10. When ethyl bromide is added to potassium t-butoxide, the product is ethyl t-butyl ether.
CH3 CH2 – Br + (CH3 )3 C – OK  (CH3 )3 C – O – CH2 CH3 
ethyl bromide potassium t  butoxide ethyl t  butyl ether
 Which of the following statement(s) is/are correct ?
(A) when the concentration of Ethyl bromide is doubled rate is also doubled.
(B) when the concentration of potassium t-butoxide is tripled and the concentration of ethyl bromide is
doubled rate will increase six times.
(C) Elimination product dominates when temperature is raised.
(D) when the concentration of potassium t-butoxide is tripled and the concentration of ethyl bromide is
doubled rate will increase three times.
11. Which of the following statement are true ?
(A) Bridgehead halide are inert for both SN1 and SN2 reaction.
(B) The first step in both SN1 and E1 reaction is same.
(C) SN2 reaction proceed with total retention of configuration.
(D) E2 elimination are favoured by weak base

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12. Which of the following reactions represent the major product.

CH CH O – CH CH O –
(A) 
3 2
 (B) 
3 2

DMSO DMF

H O
(C) 
2
 (D)

13. Which of the following statements is/are correct for alkyl halide ?
(A) In most unimolecular reactions of alkyl halide SN1 reaction is favoured over E1 reaction.
(B) E1 mechanism is favoured as compared to SN1 mechanism by branching at carbon
(C) In unimolecular reaction, increasing the temperature favours E1 mechanism
(D) E1 reactions are favoured by the use of weak bases and by the use of polar solvents.
14. The correct statements about the following reaction are

[Hint : Al2O3 gives saytzeff's product without any rearrangment]

(A) The product P is (B) The product Q is

(C) The product R is

(D) The compound gives product (P) on treatment with conc. H2SO4 as well as with Al2O3/

Section-3 : (One Integer Value Correct Type.)

This section contains 4 questions. Each question, when worked out will result in one integer
from 0 to 9 (both inclusive)
15. The order of following reaction is :

H SO / 

2 4


16.^ Total number of alkenes obtained by dehydration of 3,4-diethylhexan-2-ol in acidic medium ?

CH3

17. CH3–C—CH–CH3

H3C Br
Report your answer as XY

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18. The number of products (stereoisomers) formed in the following reaction is (consider only major
product)

SECTION-4 : Comprehension Type (Only One options correct)

This section contains 1 paragraphs, each describing theory, experiments, data etc. 3 questions
relate to the paragraph. Each question has only one correct answer among the four given
options (A), (B), (C) and (D)

Paragraph for Questions 19 to 21

The elimination reactions mainly involve three mechanism E1, E2, E1cB. If the leaving group departs
before -proton (Hion) then it is E1 mechanism, If proton is taken off first before leaving group it is
E1cB mechanism. The pure E2 involves both -Hydrogen and leaving group departing simutaneously.
If acidity of -Hydrogen increases and leaving group ability decreases then E1cB mechanism
increases.

C H O– (excess) / 
19. 2 5
 P (major)


Product P is

(A) (B) (C) (D)


20.  

The alkene formed as a major product in the above elimination reaction is

(A) CH2=CH2 (B) CH3–CH2–CH=CH2 (C) (D)

21. Which of the following substrate will undergo fastest reaction through E1cB route

(A) (B) (C) (D)

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Organic Reaction Mechanisms-IV

SECTION-5 : Matching List Type (Only One options correct)

This section contains 1 questions, each having two matching lists. Choices for the correct
combination of elements from List-I and List-II are given as options (A), (B), (C) and (D) out of
which one is correct

22. Match List I (Reaction) with List II (Type of reaction) and select the correct answer using the code given
below the lists :
List I List II

(P) CH CH O – (1) E1

3 2



3CH CH O –
2
(Q)   (2) E2
CH3CH2 OD

Ag O, moist

2

(R) (3) E1cB

(S) (4) SN1

Conc. H PO A

3 4


Codes :
P Q R S P Q R S
(A) 1 3 4 2 (B) 3 4 2 1
(C) 1 3 2 4 (D) 2 3 4 1

Practice Test-2 ( (IIT-JEE (ADVANCED Pattern))

OBJECTIVE RESPONSE SHEET (ORS)

Que. 1 2 3 4 5 6 7 8 9 10

Ans.

Que. 11 12 13 14 15 16 17 18 19 20

Ans.

Que. 21 22

Ans.

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Organic Reaction Mechanisms-IV

PART - I
1. (3) 2. (3) 3. (2) 4. (3) 5. (3)
6. (3) 7. (1) 8. (4) 9. (3) 10. (4)
11. (3) 12. (2) 13. (4) 14. (3) 15. (3)
16. (2) 17. (1) 18. (3) 19. (3) 20. (3)
21. (1) 22. (2) 23. (4) 24. (1) 25. (3)
26. (1) 27. (3) 28. (2) 29. (3) 30. (2)

PART - II
1. (A) 2. (B) 3. (A) 4. (C) 5. (B)
6. (D) 7. (C) 8. (C) 9. (A) 10. (D)
11. (A) 12. (A) 13. (D) 14. (D) 15. (B)
16. (BC) 17. (B)

PART - III
1. (C) 2. (C) 3. (C) 4. (B) 5. (C)

6. (C) 7. (A) 8. (B) 9. (BC) 10. (ABC)

11. (AB) 12. (ABD) 13. (ABCD) 14. (BD) 15. 1
16. 5 17. 33 18. 1 19. (C) 20. (A)
21. (D) 22. (D)

PART - I
CH3 CH3 CH3 CH3
OH
H2 SO 4
3.   
–H2O

O OH O
NaOH,
4.  (E1cB mechanism)

Conc. H SO –H
6. 
2 4
   

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Organic Reaction Mechanisms-IV

Alc. KOH
7.  

No anti -H is present.

C H O– K 
8. 2 5



OH
CrO3 / H 1) CH3MgBr H  
9. 
 

  
OH O 2) H3O E1
R
CH3

Br
Conc. HBr NaNH / NH (  )
10. Ph   
2 3

OH Ph Ph

C H O– K 
11. 2 5



12.

13. Self understood

t BuOH
14. + t-BuO–K+  

17. The reaction follows E1cb mechanism in which reactant undergoes D exchange alongwith an
elimination product.
+ CH3 CH3
CH2OH CH2 CH3
H  Carbocation + elimination 
18.     +

H2O rearrangement
H
19. It is a basic fact.
C H O –Na H / Ni
20. 2 5
  
2

E2

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Organic Reaction Mechanisms-IV

H SO
22. 
2 4
 (Pinacol–Pinacolone rearrangement).


23. -elimination is that elimination reaction in which substrate looses two atoms from 1 & 2 position.

CH  CH + HCl

NaNH2 is strong base so give -elimination reaction.

HBr alc. KOH HBr

25.     
R 2O2

–HBr
26. The T.S. involves 

alc. KOH 2
HBr / R O2
27. CH3  CH  CH3  CH3–CH=CH2  CH3  CH2  CH2
| |
Br Br

CH3  CH2  CH2

|
I

PART - III
1. The more stable conformation of chlorocyclohexane does not undergo an E-2 elimination easily while
the less stable conformer, with the chloro group in the axial position, readily undergoes an E-2 reaction.
2. [C] is incorrect because more than one isomer gives a single alkene on E2 elimination.
HIO4
2 0

3. [X] =

OH OH H2SO4
Pinacol-pinacolone
Rearrangement
O

4. 

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Organic Reaction Mechanisms-IV

5.


H
7.   
 
H2 O* H

8. 

 No E2 reaction because -hydrogen and leaving group not present in anti

position.
11. In SN2 reaction inversion takes place.

12. Correct product for (C) option.

H O

2


13. All statement are correct.

Conc. H SO O
14. 
2 4
 3
  (Q)
 Zn / H2 O

O
3
 
Zn / H2 O

15. E1

(cis + Trans)
OH
conc. H2SO4
 * + +
16.^

(d + ) (E + Z)

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Organic Reaction Mechanisms-IV
CH3 CH3
SN1
CH3–C—CH–CH3 + CH3–C—CH–CH3
CH3
H3C OC2H5 H5C2O CH3
C2H2OH (d+)
17. CH3–C—CH–CH3  
CH3 CH3 CH3
H3C Br
E1
CH3–C=C–CH3 + CH3–C—CH=CH2 + CH2=C–CH–CH3

CH3 CH3 CH3

18. Only one product (Single stereoisomer)

(Trans-Trans)

C H O– (excess) / 
19. 2 5



20. CH2=CH2

21. –I and –M group increases acidic strength.

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