CLIP

(HYDROCARBONS)

PART-I : SUBJECTIVE QUESTIONS

Section (A) : Free radical substitution & free radical addition reaction.
1. How do you account for formation of ethane during chlorination of methane ?

2. Calculate the relative amount of 1 and 2-Bromopropane obtained from the bromination of propane. The relative
reactivity of 1º : 2º : 3º hydrogen atom towards bromination is 1 : 82 : 1600.

3. Give the major product of monobromination of following compounds.

(a) (b) (c) (d)

4. Predict the product of the reaction given below :

HBr
CH3–CH2–CH=CH2
Peroxide
or light

5. CH2 = CH – CH2 – CH3 NBS B+C

write structure of B and C.

6. How many alkanes having molecular weight 100 are chiral ?

Section (B) : Electrophilic addition reaction

7. What will be order of reactivity of following compounds towards electrophilic addition reaction?
(I) CH2=CH2 (II) CH3–CH=CH2 (III) (CH3)2C=CH2 (IV) CH3–CH=CH–CH3

8. In the reaction sequence,

HBr
B

What is the relationship between A & B :

9. What will happen when Br2/CCl4 react with (a) cis But-2-ene (b) trans But-2-ene.

10. How many gram of Br2 will react with 5 gram of given compounds ?
(a) Pent-1-ene (b) Pent-1-yne (c) Pentane + U.V. rays

11. Give the total isomeric products formed when one equivalent of HBr is added to buta-1, 3-diene ?

Section (C) : Electrophilic subsitution reaction of aromatic compounds

12. Normally, benzene gives electrophilic substitution reaction rather than electrophilic addition reaction although
it has double bonds. Explain why?
13. How many of the following groups on benzene ring are ortho-para director ?

(a) (b) (c) (d)

(e) (f) (g) (h)

14. How many of the following benzene rings contain deactivating groups ?

(a) (b) (c) (d)

(e) (f) (g) (h)

15. Arrange the followings in decreasing order of their reactivity with an electrophile.
(I) (II) (III)

(a)

(b)

(c)

(d)

16. The number of benzylic hydrogen atom(s) in cumene is :-

17. In the following reaction electrophile attack at which position ?

H3 C NH2

5 CH2 CH3 Br2 /CCl 4

4 3 2 1
18. Write the product given reactions :

anhy.
anhy. + CH2Cl2 AlCl
(a) + CH2Cl2 AlCl 3 (b) 3

(excess)

anhy. anhy.
(c) + CHCl3 AlCl (d) + CCl4 AlCl3
3

(excess) (excess)

Cl Cl
anhy. anhy.
(e) AlCl3 (f) AlCl3

Cl anhy. O
(g) (h) AlCl3
+ Cl AlCl3 + Cl–C–Cl
(1 eq.)

Cl
AlCl3
(i)
O

PART-II : OBJECTIVE QUESTIONS

Section (A) : Free radical substitution & free radical addition reaction
1. In the free radical chlorination of methane, the chain initiating step involves the formation of –
(A) Chlorine radical (B) Hydrogen chloride (C) Methyl radical (D) Chloromethyl radical.

2. Which of the following cannot be considered as a step of mechanism in chain reaction of methane with CI2?

(A) Cl2 2CI · (B) CH4 + CI· CH3CI + H ·

·
(C) CI + CH4 ·
CH3 + HCI (D) CI· + CH · 3
CH3CI

3. The maximum ease of abstraction of a hydrogen atom by a chlorine atom is shown by –

(A) (CH3)3C–CH3 (B) (CH3)2CH2 (C) C6H5CH3 (D) CH2 = CHCH3

4. Methane reacts with excess of chlorine in diffused sunlight to give the final product as
(A) Chloroform (B) Methyl chloride. (C) Methylene chloride (D) Carbon tetrachloride

5. What will the chief product obtained when n-butane is treated with Br2 in the presence of light at 130°C ?
(A) CH3 – CH2 – CHBr – CH3 (B) (CH3)2CHCH2Br
(C) (CH3)3CBr (D) CH3 – CH2 – CH2 – CH2 – Br
6. Consider the following reactions –

H3C CH CH CH 3 + ‘X’ + HBr

| |
D CH3
Identify the structure of the major product ‘X’

(A) H3 C CH CH CH 2 (B) H3 C CH C CH 3
| | | |
D CH 3 D CH3

(C) H3 C C CH CH 3 (D) H3 C C H CH CH3

| | |
D CH 3 CH 2

7. Which of the following statement is correct in relation to the halogenation of alkane ?

(A) The reactivity of chlorine is less than bromine towards alkanes.
•
(B) For photochemical chlorination of methane, C l is formed in slowest step.
(C) Free radicals are pyramidal intermediate, stabilised by hyperconjugation and resonance.
(D) Bromination has much higher regioselective than chlorination in abstracting 30 hydrogen.

8. Which statement is incorrect about free radical halogenation of alkanes ?

(A) The number of product molecules formed by one photon is very high.
(B) If O2 is added, initially the rate of reaction decreases, then increases.
(C) Inhibitors combine with free radical and terminate the chain reaction.
(D) Presence of C 6H5 C O O C C 6H5 inhibits the free radical reaction.
O O

Cl2, 500 C
9. CH3CH = CH2 P, Product P is :
(A) CH3 CH CH2 (B) CH2 CH CH2 (C) CH3 C CH2 (D) CH3 – CH = CH – Cl
| | | |
Cl Cl Cl Cl

10. NBS Product is

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

Section (B) : Electrophilic addition reaction
11. What is the correct reactivity order of electrophilic addition reactions in the following compounds ?

(I) (II) (III) (IV)

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

12. Arrange the following in decreasing order of reactivity with HBr :

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

13. The correct order of alkenes reactivity towards an electrophile is mentioned in-
(A) CH2=CH–Cl > CH2=CH–OCH3 (B) CH2=CHCl < CH2=CCl2
(C) ethene > propene (D) CH2 = CH – OCH3 > CH2=CH–

14. + Br2 P, P will have configuration :

H
(A) (B) (C) (D) none is true
Br

CCl4
15. + Br2 Product is :

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

16. + ICI P (major product), Here 'P' is :

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

17. P
Identify major product 'P'.
(A) CCI3CHCH2CI (B) CCI3CHCH2OH (C) CCI3CHCH2 (D) CCI3CHCH2

OH CI CI CI OHOH

dil. H2SO4
18. Ph – CH2 – CH = CH2 X,
Identify major product 'X' is :

H H
| |
(A) Ph – CH2 – CH2 – CH2 – OH (B) Ph C C CH3
| |
H OH

H H
| |
(C) Ph C C CH3 (D) Ph – CH2 – OH
| |
OH H

19. In the presence of peroxide, hydrogen chloride and hydrogen iodide do not give anti–Markovnikov addition to
alkene because –
(A) both are highly ionic (B) one is oxidising and the other is reducing
(C) one of the step is endothermic in both the cases (D) all the steps are exothermic in both cases

20. The reaction of propene with HOCl proceeds via the addition of –
(A) H+ in first step (B) Cl+ in first step
–
(C) OH in first step (D) Cl+ and OH– in single step

21. CH3–CH=CH2 + NOCl Major product

Identify the product.

NO
|
(A) CH3 CH CH 2 (B) CH3 CH CH 2 (C) CH 3 CH 2 CH (D) CH 2 CH 2 CH 2
| | | | | | |
Cl NO NO Cl Cl NO Cl

22. X,

Identify product X is :
(A) (B) (C) (D)

23. Alkynes are less reactive than alkenes towards addition of Br2 because :
(A) CH = CH is less stable than CH 2 – CH 2 (B) CH = CH is more stable than CH 2 – CH 2
+
Br +
Br Br+ Br+
(C) Both are equally stable (D) Original statement is incorrect
 BH3 / THF HgSO 4
24. R P Q
H 2O2 / OH – H 2SO 4

Q & R are identical when P is –

(A) HC CH (B) CH3–C CH (C) CH3–C C–CH3 (D) Both A and C

HBr

25. CH2=CH–CH=CH2 Br
HBr

Br
At given temperature, these reactions tell about control of reaction which is :
(1) (2)
(A) Kinetic Thermodynamic
(B) Thermodynamic Kinetic
(C) Kinetic Kinetic
(D) Thermodynamic Thermodynamic

26. The reaction of one equivalent of HBr with CH2=CH–C CH gives :

(A) CH2=CH–C CBr (B) CH2=CH– C CH2 (C) CH3– CH –C CH (D) CH2=CH–CH=CHBr
| |
Br Br

HgSO 4
27. C6H5–C C–CH3 Product is :
H 2SO 4

(A) (B)

(C) C6 H5 C CHCH 3 (D) C6 H 5 CH C CH 3

| |
OH OH

Section (C) : Electrophilic substitution reaction of aromatic compounds

28. Which can be used to generate NO2+ in nitration of benzene ring ?
(A) HNO3 + H2SO4 (B) HNO3 + HClO4 (C) Solid N2O5 (D) All

29. For the electrophilic substitution reaction involving nitration, which of the following sequence regarding the

rate of reaction is true?

(A) k C H > k C D > k C T (B) k C H < k C D < k C T

6 6 6 6 6 6 6 6 6 6 6 6

(C) k C H = k C D = k C T (D) k C H > k C D < k C T

6 6 6 6 6 6 6 6 6 6 6 6

30. For the electrophilic substitution reaction involving sulphonation, which of the following sequence regarding
the rate of reaction is true?

(A) k C H > k C D > k C T (B) k C H < k C D < k C T

6 6 6 6 6 6 6 6 6 6 6 6

(C) k C H = k C D = k C T (D) k C H > k C D < k C T

6 6 6 6 6 6 6 6 6 6 6 6
31. Reaction of SO3 is easier in –

(A) benzene (B) toluene (C) nitrobenzene (D) chlorobenzene

32. Which order is correct for the decreasing reactivity to ring monobromination of the following compounds ?

(I) C6H5CH3 (II) C6H5COOH (III) C6H6 (IV) C6H5NO2

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

33. Which of the following will undergo sulphonation at the fastest rate ?

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

AlCl 3
34. + CH3 CH2CH2CH2 Cl hydrocarbon (X), major product X is:

CH 3
|
(A) CH 2CH CH3 (B) C CH 3
| |
CH3 CH 3

(C) CH2CH2CH2CH3 (D) None is correct

35. o/p Ratio is highest for nitration of which of the following compound ?
(A) Ethyl benzene (B) Toluene
(C) Isopropyl benzene (D) Tertiarybutyl benzene

CH 3COCl Zn Hg
36. C6H6 A B
AlCl 3 HCl

The end product in the above sequence is:

(A) toluene (B) ethyl benzene (C) benzophenone (D) acetophenone

37. For preparing monoalkyl benzene, acylation process is preferred than direct alkylation because
(A) In alkylation, a poisonous gas is evolved
(B) In alkylation, large amount of heat is evolved
(C) In alkylation, polyalkylated product is formed
(D) Alkylation is very costly
38. p-Nitrotoluene on further nitration gives:
CH2–NO2

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

NO2

39. Ring nitration of dimethyl benzene results in the formation of only one nitro dimethyl benzene. The dimethyl
benzene is:
CH3
CH3
(A) (B) (C) (D) None of these
CH3 CH3

40. If meta-nitroaniline is chlorinated, the major product is:

NH2 NH2 NH2 NH2
Cl Cl
(A) (B) (C) (D)
NO2 NO2 Cl NO2 NO2
Cl
41. If p-methoxy toluene is nitrated, the major product is:
CH3 CH3
NO2
(A) (B) (C) (D) No reaction
NO2
OCH3 OCH3

42. The highest yield of m-product is possible by the electrophilic substitution, in which of the following ?

(A) C6H5CH3 (B) C6H5CH2COOC2H5

(C) C6H5CH(COOC2H5)2 (D) C6H5C(COOC2H5)3

Br2
43.
Fe
Major product of above reaction is:

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

46/72
 CH2CH3
HBr Anhydrous AlBr3
44. H2 O2
Major product

CH2CH3 CH2CH3
CH 2CH3 CH 2CH3

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

AlCl3
45. Major product
Cl

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

PART-III : MATCH THE COLUMN

1. Match List-I with List-II.

List-I (Reaction) List-II (Reagents)
(A) CH3–CH=CH2 CH3–CHBr–CH3 (P) HBr
(B) CH3–CH=CH2 CH3–CH2–CH2Br (Q) Br2 / CCl4
(C) CH3–CH=CH2 BrCH2–CH=CH2 (R) HBr / Peroxide
(D) CH3–CH=CH2 CH3–CHBr–CH2Br (S) NBS

2. Match List I (reactions) with List II (type of mechanisms) and select the correct answer using the code given
below the lists :
List - I List- II
Br2 / h
(A) Ph–CH2–CH3 (P) Electrophilic substitution
dil.H2SO4
(B) Ph–CH=CH2 (Q) Electrophilic addition
HBr / R2O2
(C) Ph–CH=CH2 (R) Free radical substitution
Br2 / Fe
(D) Ph–CH2–CH3 (S) Free radical addition
 PART - I : OBJECTIVE QUESTIONS
1. Which of the following is correct potential energy diagram for the given chain propagation step ?

CH3 – H F C H3 H–F Ho –134 kJ / mol

B.E. 435 B.E. 569

(A) (B)

(C) (D)

2. Which statement is correct about photochemical bromination of butane ?

Br2 , h
CH3 – CH2 – CH2 – CH3
(A) 1-Bromobutane and 2-bromobutanes are formed in equal amounts.
(B) 2-Bromobutane is formed with faster rate than 2-chlorobutane in the other experiment of chlorination.
(C) The major product is an equimolar mixture of two compounds
(D) Homolysis of C – H bond has lower activation energy than homolysis of Br – Br bond.

3.

Order of rate of electrophilic addition reaction with HBr will be :

(A) IV> I > III > II (B) I > II > III > IV (C) I > III > II > IV (D) IV > I > II > III
4. Br2 P

Identify the major product 'P'.

Br

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

HOBr
5. cis-2-Butene P,,
Identify the product 'P'.

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

6. In the given reaction major product 'X' will be :

(A) (B)

(C) (D)

H3 O
7. major product is

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

8.

X, Y, Z reaction are respectively.

(A) Simple hydration reactions.
(B) Hydroboration oxidation, hydration and oxymercuration demercuration.
(C) Hydroboration oxidation, oxymercuration demercuration and hydration.
(D) Oxymercuration demercuration, hydroboration oxidation and hydration.

9. Which of the following species is expected to have maximum enthalpy in an electrophilic aromatic substitution
reaction ?

H E

+ E+
+

(I) (II) (III) (IV) (V)

(A) Species (II) (B) Species (III) (C) Species (IV) (D) Species (V)

(i ) Cl 2 / Fe
10. ( ii) H2O, , H Identify the product

Cl Br Br
Br
Cl Cl Cl
(A) (B) (C) (D)

SO3H OH SO3H

11. Major product of this reaction will be :

CH3 Cl,AlCl3
HCl,

(A) o-Xylene (B) p-Xylene (C) both A and B (D) m-Xylene

12. Which step is used to produce 1–Chloro–3–ethylbenzene ?

(A) Cl2 / AlCl3 Zn Hg / HCl

(B) Cl2 / AlCl3 Zn Hg / HCl

(C) Cl 2 / AlCl 3

Cl 2 / Fe
(D)

O
CH3O
13. Cl AlCl3 Major product

O Cl
CH3 O CH3O CH3O
CH3O
(A) (B) (C) (D)
O O O

Ph
+
Hg(OAc)2 + H2O H
14. Major product
NaBH4

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

PART - II : NUMERICAL TYPE QUESTIONS

1. For the given reaction how many products (consider all isomers) are optically active ?

CH3 CH3
| |
CH3 C CH2 CH CH3 Br2 / h
|
CH3

2. The number of possible enantiomeric pairs that can be produced during monochlorination of 2-methylbutane
is

3. How many products are formed when 1,5-dimethylcyclopentene react with HBr in presence of peroxide ?

4. How many dibromo derivatives are formed when bromine is added to 3-methylcyclohexene in presence of
CCl4 ?
5. Mixture of one mole each of ethene and propyne on reaction with Na will form H2 gas at S.T.P. Amount of H2

(in litre) gas will be –

6. + HBr products

How many total products will be formed in the above reaction ?

7. How many of following compounds are less reactive than benzene for sulphonation by conc. H2SO4 ?

O
+
OH CH3 NO2 Cl COOPh NMe3 NH–C–CH3 D
D D

D D
D

Br (Monobro mination)
8.

The substitution will mainly take place at which position ?

9. When ortho dibromobenzene is subjected to mononitration, X number of product are formed and when
meta dibormobenzene is subjected to mononitration, Y number of products are formed. Report your
answer as XY.

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

Cl2, heat or
1. Products
light

Sec-butylchloride
Which statement is/are correct ?
(A) One of the product exist as three stereoisomers
(B) Only two pair of diastereomers are obtained
(C) Only one meso stereoisomer is obtained
(D) Two pair of enantiomers are obtained

NBS
2. CH2 = CHCH2CH = CH2 Product is/are
(A) (B) CH2 = CH – CH = CH – CH2 – Br

(C) CH2 = CHCH2CH = CHBr (D)

3. In which reaction the product follows anti Markovnikov's rule ?

HCl HCl
(A) CF3CH=CH2 (B) ClCH=CH2
HCl HCl
(C) CH3OCH=CH2 (D) Ph–CH=CH2
4. Which of the following will give same product with HBr in presence or absence of peroxide ?

(A) Cyclohexene (B) 1-Methylcyclohexene

(C) 1,2-Dimethylcyclohexene (D) 1-Butene

5. Which of the following compounds will give same major product on acid catalysed hydration ?

(A) (B)

(C) (D)

(i ) B2H6 / THF
6.
( ii) H2O 2 / O H

True statement(s) about above reaction is/are -

(A) Reagent involve stereospecific syn addition of H and OH species.
(B) Product obtained is trans isomer.
(C) Boron atom acts as electrophile.
(D) Two stereoisomers are obtained as product.

HgSO4, H2SO 4

7. 1–Pentyne
B2H6/H2O2, OH

X and Y can be distinguished by :

(A) Silver-mirror test (B) Iodoform test (C) 2,4-DNP (D) Fehling solution

8. In which of the following reaction t-butylbenzene is formed ?

AlCl 3 BF3 . HF
(A) Benzene + iso-butyl chloride (B) Benzene + (CH3)2C = CH2

H 2SO 4 H
(C) Benzene + t-butyl alcohol (D) Benzene + (CH3)2 C= CH2

9. The replacement of a hydrogen atom in benzene by alkyl group can be brought about with which of the
following reagents ?
(A) Alkyl chloride and AlCl3 (B) Alkene and AlCl3
(C) Alkanol and alkali (D) Alkanol and acid

10. A good method for converting benzene into n-propyl benzene is:
(A) C6H6 + CH3CH2CH2Cl + Anhyd. AlCl3
(B) C6H6 + CH3CH2COCl + Anhyd. AlCl3 and then treatment with Zn/Hg/HCl
(C) C6H6 + CH3CH2COCl + Anhyd. AlCl3 and then treatment with H2 /Ni
(D) C6H6 + CH2=CH–CH2Cl + Anhyd. AlCl3 + H2/Ni
11. Which of the following statements is/are not true?

(A) All ortho-para directing groups activates the ring towards electrophilic substitution.

(B) Halobenzene is ortho para directing but deactivating in nature.

(C) All meta-directing groups must have -bond on the atom directly attached to the ring.

(D) All meta directing groups are deactivating.

12. Which of the following is not an ortho-para directing group?

(A) CF3 (B) CCl3 (C) –CH=CH–COOH (D) – N C

13. Which of the following does not give Friedel-Craft's reaction?

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

COOH
Cl
(1) SOCl2
14. Major product
(2) AlCl3

O Cl O
Cl
(A) (B)

O Cl O
Cl
(C) (D)

Ph
BH3 + THF H2 SO 4
15. Major Product
H2 O2 + OH

(A) (B)
Ph Ph
Ph

(C) (D)
Ph
 PART - IV : COMPREHENSION
Read the following passage carefully and answer the questions.

Comprehension # 1
Three acyclic alkenes (x, y, z) on catalytic hydrogenation give same alkane. On reaction with HCl, (x, y, z)
form same major tertiary halide product. Reductive ozonolysis of mixture of (x, y, z) gives a mixture of two
moles of CH2=O one moles of CH3CH=O one mole of acetone, one mole of butanone and one mole of
2-methyl propanal. x, y and z do not have any stereoisomers.

1. Alkene x, y, z are
(A) chain isomers (B) Position isomers (C) Geometrical isomers (D) Optical isomers

H3 O
2. (x, y, z) addition product. The correct statement is -

(A) All three alkenes will give 3 different major hydration products
(B) Three alkenes will give same major hydration product
(C) Two alkenes form same product but one alkene forms different major product.
(D) Addition of HCl and H3O+ both are following different regioselectivity.

3. What is true about x, y, z ?

(A) These have molecular formula C3H6
(B) x, y, z on catalytic hydrogenation give chiral alkanes.
(C) These are unbranched alkenes.
(D) These form same carbocation intermediate on reaction with HCl to give the major product.

Comprehension # 2
A Hydrocarbon X (M.F. C4H6) produces an aldehyde Y through Hydroboration-Oxidation and a ketone Z
through Oxymercuration-Demercuration. Y and Z are functional isomers. X gives P when treated with excess
of HOCl and Q when treated with excess of HCl.

4. The structure of X is :
(A) CH3–C C–CH3 (B) CH3–CH2C CH (C) CH2=CH–CH=CH2 (D) CH2=CH–C CH

5. The correct statement is :

(A) P and Q are positional isomers. (B) Q is 1,2-Dichlorobutane.
(C) P is 1,1-Dichlorobutan-2-one. (D) P and Q are identical.
 PART- I
1. The compounds P, Q and S

O
COOH OCH3 C
O
HO H3 C
P Q S

were separately subjected to nitration using HNO3 / H2SO4 mixture. The product formed in each case
respectively, is

COOH OCH3 O
(A) C
HO H3 C O
NO2 NO2 O2 N

COOH OCH3 O
(B) C
HO NO2 H3C O
NO2 NO2

O NO2
COOH OCH3
C
(C) O
HO H3 C NO2
NO2

O
COOH OCH3
C
(D) O NO2
HO H3C NO2
NO2

2. The major product of the following reaction is

RCH2OH
O H anhydrous
(A) a hemiacetal (B) an acetal
(C) an ether (D) an ester
3. The maximum number of isomers (including stereoisomers) that are possible on monochlorination of the
following compound, is :

4. Different possible thermal decomposition pathways for peroxyesters are shown below. Match each pathway
from List-I with an appropriate structure from List-II and select the correct answer using the code given below the
lists.
P
–CO2
·
R + R'O ·

Q
–CO2
·
R + R'O · · ·
R + X + carbonyl compound

O
O
R O R'
(Peroxyester)
R
·
RCO2+ R'O ·–CO R·+ X· + carbonyl compound
2

S
·
RCO2+ R'O ·–CO R·+ R'O·
2

List-I List-II
O
(P) Pathway P (1)
C6H5CH2 O O CH3
O
(Q) Pathway Q (2)
C6H5 O O CH3
O CH3
(R) Pathway R (3) C6H5CH2 O O CH3
CH2C6H5
O CH3
(S) Pathway S (4) C6H5 O O CH3
C6H5
Code :
P Q R S
(A) 1 3 4 2
(B) 2 4 3 1
(C) 4 1 2 3
(D) 3 2 1 4
5. In the following reaction, the major product is -

CH3
1 equivalent HBr
CH2
H2 C

CH3 CH3 CH3 CH3

CH3 CH2
(A) CH2 (B) H3C (C) H2C Br (D) H3C Br
Br Br

6. In the following monobromination reaction, the number of possible chiral products is

CH2CH2CH3
Br2(1.0 mole)
H Br
300°C
CH3
(1.0 mole)
(enantiomerically pure)

7. Among the following reaction(s) which give(s) tert-butyl benzene as the major product is(are)

Br
Cl
(A) (B)
NaOC2H5 AlCl3

OH
(C) (D)
H2SO 4 BF3.OEt2

8. The correct statement(s) for the following addition reactions is(are)

H3 C H
Br2 / CHCl3
(i) M and N
H CH3

H3 C CH3 Br2/CHCl3
(ii) O and P
H H
(A) (M and O) and (N and P) are two pairs of enantiomers.
(B) Bromination proceeds through trans-addition in both the reactions.
(C) O and P are identical molecules.
(D) (M and O) and (N and P) are two pairs of diastereomers.
 PART - II
1. How many chiral compounds are possible on monochlorination of 2-methylbutane?

(1) 8 (2) 2 (3) 4 (4) 6

2. Which branched chain isomer of the hydrocarbon with molecular mass 72u gives only one isomer of mono
substituted alkyl halide ?
(1) Tertiary butyl chloride (2) Neopentane
(3) Isohexane (4) Neohexane

3. In the hydroboration - oxidation reaction of propene with diborane, H2O2 and NaOH, the organic compound formed

is :
(1) CH3CH2CH2OH (2) (CH3)3COH (3) CH3CHOHCH3 (4) CH3CH2OH

4. CH2–CH=CH2 on mercuration- demercuration produces the major product :-

CH2–CH–CH3 CH 2–CH 2–CH 2–OH

(1) (2)
OH

(3)
CH2–COOH (4)
CH2–CH–CH2
OH OH

5. The major product obtained in the photo catalysed bromination of 2-methylbutane is :-

(1) 2-Bromo-2-methylbutane (2) 2-Bromo-3-methylbutane

(3) 1-Bromo-2-methylbutane (4) 1-Bromo-3-methylbutane

6. In the presence of peroxide, HCl and HI do not give anti-Markownikoff s addition to alkenes because
(1) All the steps are exothermic in HCl and HI
(2) One of the steps is endothermic in HCl and HI
(3) HCl is oxidizing and the HI is reducing
(4) Both HCl and HI are strong acids

7. What is the major product expected from the following reaction ?

CH3
D Cl

Where D is an isotope of hydrogen.

D CH3 CH3 D
Cl D H H
(1) CH3 (2) Cl (3) Cl (4) CH3
H H D Cl
8. Consider the reaction sequence below :

OCH3
Succinic Anhydride Clemmenson's
AlCl3 A reduction
X;

X is :

OCH3 OH
OH OCH3
H 3CO H3CO
(1) (2) (3) (4)

OH
OH

9. Bromination of cyclohexene under conditions given below yields :

Br2 / h

Br
Br Br Br

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

Br Br
Br

10. The major product of the following reaction is:-

Br
(1) (2) (3) (4)
Br
Br
11. Which of the following compounds will not undergo Friedel Craft's reaction with benzene ?

COCl Cl
Cl
(1) (2) (3) (4)
Cl
O
12. The increasing order of nitration of the following compound is :-

NH2 Cl OCH3 CH3

(a) (b) (c) (d)

(1) (b) < (a) < (c) < (d) (2) (b) < (a) < (d) < (c)
(3) (a) < (b) < (c) < (d) (4) (a) < (b) < (d) < (c)
13. The major product of the following reaction is:
O OH
CH3
O+
AlCl3,

OH OH
H 3C CH3

(1) O (2)
O

OH OH
CH3 CH3

(3) (4)
O

14. Which of the following compounds is not aromatic ?

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

N H

15. The major product of the following reaction is:

CH3O
(i) AlCl3 (anhyd.)
CH2Cl (ii) H 2O

CH3O CH 3O
CH3O
CH3O CH3
(1) (2) (3) (4)
CH3
16. What will be the major product in the following mononitration reaction ?

O
N HNO3
H Conc. H2SO4

O NO2 O
(1) N (2) O 2N N
H H

O 2N O
O
N
(3) N (4) H
H O2N

17. Which compound(s) out of the following is/are not aromatic ?

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

(1) C and D (2) B, C and D (3) A and C (4) B

18. The major product of the following reaction is :-

HO (1) HCl
(2) AlCl3 (Anhyd.)

Cl HO Cl HO
(1) (2) (3) (4)

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19. The major product of the following reaction is :

CH3O (1) Cl2/CCl4

(2) AlCl3(anhyd.)

Cl Cl
CH3O CH3O
(1) CH3O (2) CH3O (3) (4)
Cl
Cl

20. Which hydrogen in compound (E) is easily replacable during bromination reaction in the presence of light ?

C H3 C H2 C H C H2

(1) – hydrogen (2) – hydrogen (3) – hydrogen (4) – hydrogen

21. The major product of the following reaction is:

H3C
CH2 HCl

CH 3 CH2–Cl
CH3
CH3
(1) Cl (2)
H H

CH3 CH3
CH2–Cl CH3
(3) (4)
H H
Cl
 ANSWER KEY
EXERCISE # 1
PART-I
1. Chlorination of methane is a free radical reaction which occurs by the following mechanism
Homolytic Fission
Initiation 2

Propagation + HCl

CH3 – Cl +

Termination CH3 – CH3 (Ethane)

CH3 – Cl

Cl – Cl

2. 2-Bromopropane = 96.5 %
1-Bromopropane = 3.5 %

3. (a) (b) (c) (d)

4. CH3–CH2– CH2–CH2
Br

5. CH2 CH – CH – CH3 + CH2 – CH CH – CH3

| |
Br Br

6. 4 7. III > IV > II > I

8. Positional isomers
A = Ph–CH2–CH2–CH2–Br
B = Ph–CH2–CH–CH 3
Br
9. (a) Racemic mixture of 2,3-Dibromobutane (b) Meso 2,3-Dibromobutane

10. (a) 11.43g Br2 ; (b) 23.53 g Br2; (c) 11.11 g Br2

11. 4
12. Benzene has resonance stabilization due to delocalisation of -electrons and during electrophilic addition
reactions, it looses its aromaticity. In electrophilic substitution reaction aromaticity is retained.

13. 5 (a , b , c , f , h) 14. 4 (c, e , g , h)

15. (a) (I) > (II) > (III) (b) (II) > (III) > (I) (c) (II) > (I) > (III) (d) (III) > (I) > (II)
16. 1 17. 2

anhy. Cl anhy.
18. (a) (b) anhy.(c)
+ CHCl

anhy. anhy.(e) anhy.

(d) Ph3C–Cl (f)

O
C–Cl
anhy.
(g) AlCl (h) (i)

(1 eq.)
O
PART-II
1. (A) 2. (B) 3. (C) 4. (D) 5. (A) 6. (B) 7. (D)
8. (D) 9. (B) 10. (D) 11. (C) 12. (B) 13. (D) 14. (B)
15. (B) 16. (B) 17. (B) 18. (C) 19. (C) 20. (B) 21. (A)
22. (B) 23. (A) 24. (D) 25. (A) 26. (B) 27. (A) 28. (D)

29. (C) 30. (A) 31. (B) 32. (B) 33. (B) 34. (D) 35. (B)

36. (B) 37. (C) 38. (A) 39. (C) 40. (B) 41. (B) 42. (D)
43. (D) 44. (A) 45. (C)
PART-III

1. (A) P ; (B) R ; (C) S ; (D) Q 2. (A) R ; (B) Q ; (C) S ; (D) P

EXERCISE # 2
PART - I
1. (C) 2. (C) 3. (D) 4. (B) 5. (B) 6. (B) 7. (C)

8. (C) 9. (A) 10. (C) 11. (D) 12. (A) 13. (A) 14. (B)
 PART - II

1. 4 2. 2 3. 8 4. 4 5. 11.2 L 6. 4 7. 4
8. 4 9. 23

PART - III

1. (ABC) 2. (AB) 3. (A) 4. (AC) 5. (ABCD) 6. (ABCD)

7. (ABD) 8. (ABCD) 9. (ABD) 10. (B,D) 11. (A,C) 12. (A,B,D)

13. (B,C,D) 14. (B) 15. (C)

PART - IV

1. (B) 2. (B) 3. (D) 4. (B) 5. (C)

EXERCISE # 3

PART- I

1. (C) 2. (B) 3. 8 4. (A) 5. (D) 6. 5 7. (BCD)

8. (BD)

PART - II
1. (3) 2. (2) 3. (1) 4. (1) 5. (1) 6. (2) 7. (2)

8. (4) 9. (2) 10. (3) 11. (1) 12. (4) 13. (1) 14. (3)

15. (2) 16. (3) 17. (2) 18. (2) 19. (4) 20. (2) 21. (1)