Structure Identification & POC

 Marked questions are recommended for Revision.

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. Marks: 100 Max. Time : 1 Hour

Important Instructions:

A. General %
1. The test paper is of 1 hour duration.
2. The Test Paper consists of 25 questions and each questions carries 4 Marks. Test Paper consists of
Two Sections.
B. Test Paper Format and its Marking Scheme:
1. Section-1 contains 20 multiple choice questions. Each question has four choices (1), (2), (3) and (4) out
of which ONE is correct. For each question in Section-1, you will be awarded 4 marks if you give the
corresponding to the correct answer and zero mark if no given answers. In all other cases, minus one
(–1) mark will be awarded.
2. Section-2 contains 5 questions. The answer to each of the question is a Numerical Value. For each
question in Section-2, you will be awarded 4 marks if you give the corresponding to the correct
answer and zero mark if no given answers. No negative marks will be answered for incorrect
answer in this section. In this section answer to each question is NUMERICAL VALUE with two digit
integer and decimal upto two digit. If the numerical value has more than two decimal places
truncate/round-off the value to TWO decimal placed.

SECTION-1
This section contains 20 multiple choice questions. Each questions has four choices (1), (2), (3) and (4)
out of which Only ONE option is correct.

1. Which of the following compound on reductive ozonolysis does not give glyoxal as one of the product?

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

2. Which alkyne will give 3-Ethyl heptane on catalytic hydrogenation?

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

3. An organic compound does not react appreciably with Lucas reagent but give white precipitate with
Tollen’s reagent. Which is the possible structure of compound ?
(1) (2)
OH
(3) (4) CH2=C=CH–CH2–OH
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Structure Identification & POC

4. Which of the following compounds will give a positive iodoform test ?
(1) Methanol (2) 2,2-Dimethylpropanol
(3) Ethanol (4) Methanal

5. The following two compounds I and II can be distinguished by using reagent?

(I) (II)

(a) aq. NaHCO3 (b) Neutral FeCl3 (c) Fehling solution (d) Na metal
(1) a or c (2) b or c (3) c or d (4) b or d

6. Which of the following compound cannot give Iodoform when react with IO–(hypoiodite)?
(1) (2)

(3) (4)

NH2 CH2–NH2

7. and can be distinguish by

Me
(1) CHCl3 + KOH (2) NaNO2 + HCl followed by -Napthol
(3) CS2 + HgCl2 (4) Na Metal

O3
8. (x) C7H12 P+Q
Me2S
Compound P responds to Tollen’s test and iodoform test but Q does not respond with both the
reagents. Structure of compound (x) is :

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

9. A research scholar get a mixture of three product during an experiment with ammonia. In product I only
one H of ammonia is replaced by ethyl group and in II two H atoms of ammonia are replaced by ethyl
groups and in III all the H-atoms are replaced by ethyl groups. Which test he should use to distinguish
or separate the products :
(1) Carbyl amine test (2) Iodoform test
(3) Fehling solution test (4) Hinsberg test

10. Which is incorrect match with respect to the reagent used for lab test ?
(1) Carbohydrates  -Naphthol (Molish reagent)
(2) Nitro ethane  Zn, NH4Cl and AgNO3 (Mulliken Barker test)
(3) Phenol  Anhydrous ZnCl2 + Conc. HCl (Lucas Reagent)
(4) Benzoic acid  NaHCO3

11. On oxidative ozonolysis of 3-Methylhex-3-ene, two products A & B are formed. A gives CO 2 gas with
sodium bicarbonate, but B can not. The structures of A & B are respectively :
(1) & CH3–CH2–COOH (2) CH3–CH2–COOH & CH3–CH2–CH=O

(3) CH3–CH2–COOH & (4) CH3–CH2–CH2–COOH &

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Structure Identification & POC

12. and can be differentiated by :

(1) Carbylamine reaction (2) Iodoform test
(3) Cold KMnO4 (4) Br2–H2O

13. Which of the following compound gives azo dye test ?

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

14. A compound (P), obtained as an ozonolysis product of (Q) gives brisk effervescence with Na, violet
coloration with neutral FeCl3 and silver mirror with Tollen's reagent. (Q) may be:

(1) (2)

(3) (4) All of these

15. Which of the following reagent can distinguish the given compound I & II ?

&

(1) Na metal (2) NaHCO3 (3) Lucas Reagent (4) 2, 4-D.N.P

16. A compound (P) on reaction with “Q” in basic medium (KOH) gives a bad smelling compound
(CH3CH2NC). Compound Q can be prepare by reaction of acetone with calciumhypochlorite (Ca(OCl) 2].
P and Q can:
(1) CH3–CH2–NH2 & CHCl3 (2) CH3–CH2–NO2 & CH3Cl
(3) CH3–CH2–NH–CH3 & COCl2 (4) (CH3–CH2) 3N & Cl2

17. Which of the following can gives Hinsberg test :

(1) CH3–CH2–OH (2) CH3–CH2–NO2 (3) CH3–CH2–NH2 (4) CH3—C—NH2
O

18. Acetaldehyde and Propyne can be distinguish by :

(i) Tollen’s reagent (ii) I2/NaOH (iii) Lucas reagent (iv) neutral FeCl3
(1) (i) , (ii) & (iii) (2) (ii) & (iii) (3) (i) & (ii) (4) (iii) & (iv)

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Structure Identification & POC

19._ Two elements X (atomic weight = 75) and Y (atomic weight = 16) combine to give a compound having
75.8% X. The formula of the compound is :
(1) XY (2) X2Y (3) X2Y2 (4) X2Y3

20._ In the carius method, halogens present in organic compounds are estimated in the form of-
(1) barium halide (2) silver halide (3) hydrogen halide (4) gaseous halogen

SECTION-2
This section contains 5 questions. Each question, when worked out will result in Numerical Value.

21. How many isomeric structural alkene on catalytic hydrogenation gives 3-Methyl hexane?

22. How many structural isomeric ketones having molecular formula (C5H10O) give iodoform test ?

H / Ni Cl / h
23. 
2
 P 
2
 Q (Total number of monochloro structural products).

24. How many hydrocarbons having molecular mass 68 can give white precipitate with Tollen's reagent

25. During estimation of nitrogen present in an organic compound by Kjeldahl’s method, the ammonia
evolved from 0.5 g of the compound in Kjeldahl’s estimation of nitrogen, neutralized 10 mL of 1 M
H2SO4. What is the percentage of nitrogen in the compound.

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

Ans.

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

1. The compound formed in the positive test for nitrogen with the Lassaigne solution of an organic
compound is - [AIEEE 2004, 3/225]
(1) Fe4[Fe(CN)6]3 (2) Na3[Fe(CN)6 (3) Fe(CN)3 (4) Na4[Fe(CN)5NOS]

2. Out of the five isomeric hexanes, the isomer which can give two monochlorinated compounds is ?
[AIEEE 2005, 3/225]
(1) n-Hexane (2) 2,3-Dimethylbutane
(3) 2,2-Dimethylbutane (4) 2-Methylpentane

3. Which of the following reagents may be used to distinguish between phenol and benzoic acid ?
[AIEEE 2011, 4/120]
(1) Aqueous NaOH (2) Tollen's reagent (3) Molisch reagent (4) Neutral FeCl3

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Structure Identification & POC

4. Ozonolysis of an organic compound 'A' produces acetone and propionaldehyde in equimolar mixture.
Identify 'A' from the following compounds : [AIEEE 2011, 4/120]
(1) 1-Pentene (2) 2-Pentene
(3) 2-Methyl-2-pentene (4) 2-Methyl-1-pentene

5. Which branched chain isomer of the hydrocarbon with molecular mass 72u gives only one isomer of
mono substituted alkyl halide ? [AIEEE 2012, 4/120]
(1) Tertiary butyl chloride (2) Neopentane
(3) Isohexane (4) Neohexane

6. Iodoform can be prepared from all except : [AIEEE 2012, 4/120]

(1) Ethyl methyl ketone (2) Isopropyl alcohol
(3) 3-Methyl-2-butanone (4) Isobutyl alcohol

7. On heating an aliphatic primary amine with chloroform and ethanolic potassium hydroxide, the organic
compound formed is : [JEE(Main)-2014, 4/120]
(1) an alkanol (2) an alkanediol (3) an alkyl cyanide (4) an alkyl isocyanide

8. For the estimation of nitrogen, 1.4 g of an organic compound was digested by Kjeldahl method and the
M
evolved ammonia was absorbed in 60 mL of sulphuric acid. The unreacted acid required 20 mL of
10
M
sodium hydroxide for complete neutralization. The percentage of nitrogen in the compound is :
10
[JEE(Main)-2014, 4/120]
(1) 6% (2) 10% (3) 3% (4) 5%

9. In Carius method of estimation of halogens, 250 mg of an organic compound gave 141 mg of AgBr. The
percentage of bromine in the compound is : (at. mass Ag = 108 ; Br = 80) [JEE(Main)-2015, 4/120]
(1) 24 (2) 36 (3) 48 (4) 60

10. Which compound would give 5-keto-2-methyl hexanal upon ozonolysis ? [JEE(Main)-2015, 4/120]
CH3 CH3 CH3
H3C
(1) (2) (3) (4)
CH3 CH3

11. Which of the following compounds will be suitable for Kjeldahl's method for nitrogen estimation ?
[JEE(Main)-2018, 4/120]
+ –
NO2 N2Cl NH2
(1) (2) (3) (4)
N

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

1. What simple laboratory test could be performed to distinguish between 1-pentyne and 2-pentyne ?
[NSEC-2000]
+
(A) the addition of Ag in ammonia (B) the addition of H2SO4 in Hg +2

(C) the addition of Br2 in CCl4 (D) the addition of H2 on a Pt catalyst.

2. Which of the following produces four monochloro derivatives on free radical chlorination? [NSEC-2000]
(A) 2, 2-dimethylbutane (B) Pentane
(C) 2, 2-dimethylpropane (D) 2-methylbutane

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Structure Identification & POC

3. Which of the following tests could be performed to distinguish between 1-butyne and 2-butyne ?
[NSEC-2001]
+
(A) Ag / NH3 (B) Br2 / CCI4 (C) H2 / Pt +2
(D) Hg / H2SO4

4. Which of the following compounds will give a positive iodoform test ? [NSEC-2001]
(A) methanol (B) 2,3-dimethyl ethanol
(C) -haloethanol (D) methanal

5. Lucas reagent is : [NSEC-2001]

(A) anhydrous CaCl2 and conc. HCl (B) anhydrous ZnCl2 and conc. HCl
(C) anhydrous AlCl3 and conc. HCl (D) anhydrous PdCl2 and conc. HCl

6. The percentage composition of the elements of C8H9ON is : [NSEC-2002]

(A) 8 : 9 : 1 : 1 (B) 71.1 : 6.7 : 11.8 : 10.4
(C) 12 : 1 : 16 : 14 (D) none of these

7. The percentage of nitrogen in a compound is determined by [NSEC-2006]

(A) Nessler`s method
(B) Kjeldahl`s method
(C) Carius method
(D) taking the difference between total percentage and the sum of percentages of all other elements
present.

8. The percentage of oxygen in a compound is determined by : [NSEC-2007]

(A) Dumas method
(B) Kjeldahl’s method
(C) Carius method
(D) subtraction the sum of percentages of all other elements present from 100.

9. In the Dumas method for the estimation of nitrogen, 0.0237 grams of an organic compound gave 2.21
mL of nitrogen at 754.32 mm of Hg pressure at 18°C. (Aqueous tension at 18°C is 15.4 mm of Hg.)
Therefore the percentage of nitrogen in the compound is : [NSEC-2008]
(A) 20.67% (B) 10.6% (C) 11.2% (D) 13.9%

10. The reagent which will be suitable to distinguish 1-methoxy-3-methyl-2-butene from isomeric 4-methyl-
3-pentene-1-ol is : [NSEC-2009]
(A) bromine in chloroform. (B) alkaline potassium permanganate.
(C) ammoniacal silver nitrate. (D) sodium metal suspended in hexane.

11. Tollen's reagent is [NSEC-2012]

(A) Cu2O (B) [Cu(OH)4]2– (C) Ag2O (D) [Ag(NH3)2]+

12. The blood red color obtained in the detection of nitrogen and sulphur together in an organic compound
in Lassaigne’s test is due to [NSEC-2013]
(A) [Fe(CNS)]+ (B) [Fe(CNS)2]+ (C) [Fe(CNS)3]– (D) [Fe(CNS)2]2+

13. Fehling solution is [NSEC-2013]

(A) AgNO3 solution + NaOH solution + NH4OH
(B) Alkaline solution of Cupric ion complexed with citrate ion
(C) Copper sulphate + sodium potassium tartarate + NaOH
(D) Copper sulphate solution

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Structure Identification & POC

14. Match the compounds given in list I with their characteristic reactions in list II [NSEC-2016]
List-I (Compound) List-II (Reaction)
1 Tert-butyl amine a Liberation of ammonia on heating with aq.NaOH
2 2-methyl-2-pentanol b Effervescence with NaHCO3
3 2,4,6-trinitrophenol c Foul smell with chloroform in alkaline condition
4 Cyclohexane d Formation of an water insoluble compound on treatment
carboxamide with conc. HCl and ZnCl2
(A) 1-a, 2-c, 3-d, 4-b (B) 1-c, 2-d, 3-b, 4-a (C) 1-a, 2-b, 3-c, 4-d (D) 1-d, 2-a, 3-b, 4-c

15. Number of products formed (ignoring stereoisomerism) in the monochlorination of ethylcyclohexane is

[NSEC-2019]
(A) 6 (B) 8 (C) 5 (D) 4

16. Atropine (C17H23O3N) is a naturally occurring compound used to treat certain types of poisoning. The
degree of unsaturation in atropine is [NSEC-2019]
(A) 7 (B) 6 (C) 5 (D) 4

17. The alkene ‘Y’ in the following reaction is [NSEC-2019]

O O O O O
(i) Ozonoly sis
Alkene Y  + + H
(ii) Me 2S H H H
O

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

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

Max. Time : 1 Hr. Max. Marks : 78

Important Instructions
A. General :
1. The test is of 1 hour duration.
2. The Test Booklet consists of 26 questions. The maximum marks are 78.
B. Question Paper Format
3. Each part consists of five sections.
4. Section-1 contains 6 multiple choice questions. Each question has four choices (A), (B), (C) and (D) out of
which ONE is correct.
5. Section-2 contains 5 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 8 questions. The answer to each of the questions is a numerical value, ranging from 0
to 9 (both inclusive).
7. Section-4 contains 2 paragraphs each describing theory, experiment and data etc. 3 & 2 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 2 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.
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Structure Identification & POC

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

1. An organic compound “A” of molecular weight 120, gives Tollen’s reagent test and 2,4-DNP test but no
Iodoform with I2/OH. The compound “A” may be :
(A) Benzoic acid (B) Phenyl methyl ketone
(C) 2-phenyl ethanal (D) 1-phenyl ethane

2. A hydrocarbon on oxidative ozonolysis produces Oxalic acid and Butanedioic acid. Its structure is

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

3. Farnesene is a compound found in the waxy coating of apples. On hydrogenation it gives 2,6,
10-Trimethyl dodecane. On ozonolysis it gives one mole acetone, one mole of formaldehyde, one mole
of 2-Methylpentanedial and one mole of 4-Oxopentanal. The structure proposed for Farnesene may be

(A) (B)

(C) (D)

4. ‘X’ compound (C4H8O) decolorises bromine water & gives instant turbidity with Lucas reagent. When ‘X’
react with I2 & NaOH it give yellow ppt Identify ‘X’.
O
(A) CH 3–C–CH 2–CH 3 (B) CH3–CH–CH=CH2
OH
CH3
(C) CH3–C–CH3 (D) CH3–HC=CH–CH2
OH OH

5. Compounds I and II can be distinguished by using reagent.

() (II)
4–Hydroxy–4–methylpent–2–enoic acid 5–Hydroxypent–2–ynoic acid

(A) NaHCO3 (B) Br2 / H2O

(C) HCl / ZnCl2 (anhydrous) (D) Cu2Cl2 / NH4OH

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Structure Identification & POC

6. Which of the following test will not be given by (Squaric acid)

(A) Br2 water test (B) 2, 4-DNP test (C) Neutral FeCl3 (D) Tollen’s test

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

This section contains 5 multiple choice questions. Each questions has four choices (A), (B), (C)
and (D) out of which ONE or MORE THAN ONE are correct.

7. Which of the following compounds after complete hydrogenation will form three monochloro structural
isomeric products ?

(A) (B)

C  CH
(C) (D) |
HC  C – CH – C  CH

8. A organic compound having molecular formula C3H4, react with sodium metal to give a colourless and
odourless gas. Select the correct statements about organic compound.
(A) It gives Bromine water test (B) It reacts with Bayer’s reagent
(C) It reacts with Tollen’s reagent (D) It reacts with Ammonical cuprous chloride.

9. Compound P Liberates H2 gas with Na metal. P gives white precipitate with tollen’s reagent, there is no
response towards Lucas reagent and compound Q gives instant turbidity with anhydrous ZnCl2 / HCl,
and with sodium metal 1 mole of compound Q liberates 11.2 litre H 2 gas at STP. Find the structural
formula of compound P and Q.
O CH3
|| |
(A) P is CH2  CH  C  H (B) Q is CH3  C  CH2  O  CH3
|
OH
CH3
|
(C) P is CH3–O–CC–H (D) Q is CH3  C  CH  CH3
| |
OH OH

CHO
(1) O3
CH3–CH
(2) Zn/H2O
CHO
10. C8H12
(X) H2/Ni
Y
True statements is/are

(A) Structure of X is .

(B) Structure of X is .

(C) Y on monochlorination produce 3 monochloro structural products.

COOH
(D) Oxidative ozonolysis product of X is CH 3–CH .
COOH
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Structure Identification & POC

11._ An unknown compound P (having fruity smell with molecular weight 172) is subjected to hydrolysed,
products (Q) & (R) are formed having same number of carbon atoms in their parent chain.
Reactions are –

H3 O
[P] Q+R
NaHCO3 aq.
[Q] S + CO2 
I2 + NaOH
[R] T + CHI3(yellow ppt.)
Predict possible structures of P, on the basis of above observations ?
O O
(A) (B)
O O
O O
(C) (D)
O O

Section-3 : (Single/ Double Integer Value Correct Type.)

This section contains 8 questions. Each question, when worked out will result in numerical
values from 0 to 9 (both inclusive)

12. How many alkenes, alkynes and alkadienes can be hydrogenated to form Isopentane (Including all
structural isomers)

13. How many acyclic structural isomeric carbonyl compound having molecular formula C 6H12O can gives
haloform test?

14. Structure of Ascorbic acid is represented as follows.

(Ascorbic acid)
How many of the following reagents can give positive test with ascorbic acid?
Na Metal HCl + ZnCl2 FeCl3
(III) (IV) (V)
NaOH + Phenopthalein dil.KMnO4 Br2/H2O AgNO3 + NH4OH I2 + NaOH
(VI) (VII) (VIII) (XI) (X)

15. Observe the the following compounds.

O Me
OH
CH3
CH3 Ph
CH3–C–OH C
CH3 O
O
(I) (II) (III) (IV) (V)
O Ph

CH3 O CH3 Ph – CH – CH3

CH3–CH–CH2–CH3 C C |
OH
OH O O (IX)
(VI) (VII) (VIII)
Number of compound which can gives positive Haloform test = (x)
Number of compound which can gives positive Lucas reagent test = (y)
Report your answer (x + y)
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Structure Identification & POC

16. ‘n’ Number of alkenes yield 2,2,3,4,4-pentamethyl-pentane on catalytic hydrogenation and ‘m’ number
of monochloro structural isomers are possible for this compound.
Report your answer as (n + m).

17._ Calculate total number of organic compounds with molecular formula C6H12O2 which gives CO2 gas
with aqueous NaHCO3 solution ?

18._ How many oxygen atoms are present in 1 molecule of ammonium phosphomolybdate ?

19._ How many organic compounds on treatment with (CH 3COO)2Pb give black precipitate in the Lassaigne
test for element detection ?
Cysteine Methionine Diethylthioether Alanine
Glycine Glucose Salicylic acid Ethylmercaptan

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

This section contains 2 paragraphs, each describing theory, experiments, data etc. Each 3 & 2
questions has only one correct answer among the four given options (A), (B), (C) and (D)

Comprehension # 1
Aldehyde and ketones may be prepared by reductive cleavage of carbon-carbon double bonds. A
particularly useful reagent for this purpose is ozone under reductive conditions results in the formation
of carbonyl compounds.

O / Zn
20. 
3
 Products
H2O

Which of the following product is not formed in above reaction -

(A) (B) O O (C) H–C–H (D) CH3 –C–H

O O
O3 / Zn
21. (X)   CO2 + CH3 –C–H + OHC–C–CHO
H2O
O O
(X) is -
CH3 H3C
(A) C C (B) C CH CH
H H3C

(C) C (D) CH3 C C

H

O / Zn
22. 
3
 Products
H2O

Which of the following product is not formed in above reaction -

Products are -
(A) H–C–H (B) OHC–C–CH 2–CHO
O O
(C) OHC–CH2–C–CH2 CHO (D) H–C–C–H
O O O
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Structure Identification & POC

Comprehension # 2
An organic compound (P) with formula C10H12 undergoes catalytic hydrogenation to yield C10H18(Q).
Compound (Q) gives three different monochlorination structures. Reductive ozonolysis of (P) gives a
single compound (R), C5H6O3.

23._ Which of the following is true ?

(A) (P) can decolorize bromine water
(B) (Q) contains a benzene ring
(C) (R) gives Tollen’s reagent test.

(D) (P) may be

24._ Identify the correct statement(s) :

(A) (P) can answer Tollen’s reagent test.
(B) (Q) is a bicyclic compound
(C) (R) can give NaHCO3 test
(D) (P) contains a benzene ring

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

This section contains 2 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.

25. Match the column :

Column-I Column-II

CH3–CH=CH–CH2– –CH3
(A) (P) Bromine water solution decolourised

(B) (Q) precipitate obtained with AgNO3 + NH4OH

(C) (R) CO2 gas liberated by NaHCO3

(D) (S) Yellow precipitate by 2, 4-DNP

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Structure Identification & POC

26._ Match the following :

Compounds Lab Test

H NH2
N
NO2
(P) Brady’s reagent test
(A)

NO2

OH
H (Q) Tollen’s reagent test
(B)
O

OH

(C) (R) Liberates H2 with Na

O

(D) HCOOH (S) Haloform test

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 23 24

Ans.

Que. 25

Ans. (A) (B) (C) (D)

Que. 26

Ans. (A) (B) (C) (D)

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Structure Identification & POC

APSP Answers

PART - I

1. (1) 2. (2) 3. (3) 4. (3) 5. (2)

6. (1) 7. (2) 8. (3) 9. (4) 10. (3)

11. (3) 12. (1) 13. (2) 14. (1) 15. (3)

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

21. 6.00 22. 2.00 23. 2.00 24. 2.00 25. 56.00

PART - II

1. (1) 2. (2) 3. (4) 4. (3) 5. (2)

6. (4) 7. (4) 8. (2) 9. (1) 10. (2)

11. (4)

PART - III

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

6. (B) 7. (B) 8. (D) 9. (B) 10. (D)

11. (D) 12. (B) 13. (C) 14. (B) 15. (A)

16. (A) 17. (C)

PART - IV

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

6. (D) 7. (CD) 8. (ABCD) 9. (BC) 10. (BCD)

11. (ABC) 12. 6 13. 4 14. 6 15. 8(5+3)

16. 4 17. 8 18. 40 19. 4 20. (D)

21. (A) 22. (D) 23. (AC) 24. (B)

25. (A) - P,S; (B) - P,Q; (C) - Q,R,S; - (D) R 26. (A) - PQR; (B) - PQRS; (C) - PRS; (D) – QR

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Structure Identification & POC

APSP Solutions

PART - I
CHO
O / Zn
1. 
3
 2HCHO +
H2O
CHO
O3 / Zn
  HCHO + + CH3CHO
H2O

O3 / Zn
  HCHO + H—C—C—C—H + CHO
H2O
O O O CHO
O / Zn

3
 O + CHO–CHO + HCHO
H2O

Ni
2. + H2 

3. Terminal alkyne gives white precipitate with Tollen's reagent and 1º alcohol do not react appreciably
with Lucas reagent.

4. , CH3–CH groups gives positive iodoform test.

|
OH

5. (a) Both does not give the test with aq. NaHCO3.
(b) II give +ve test with neutral FeCl3 due to presence of phenolic –OH group, but (I) does not.
(c) In (I) aromatic aldehyde does not give Fehling test but (II) gives.
(d) In (I) and (II) acidic hydrogen atom is present so both give +ve test with Na metal.

6. , CH3–CH groups gives positive iodoform test.

|
OH

NH2

(1) NaNO HCl

7. 
2
 Orange–Red dye
(2)  -Napthol
Me
CH2–NH2 CH2–OH

NaNO HCl

2
 + N2

O3
8. CH3CHO +
Me2S

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Structure Identification & POC

9. 1º, 2º and 3º amine mixture can be seperated by Hinsberg reagent.

10. Phenol does not gives Lucas reagent test.

O /H O
11. 
3 2
 CH3–CH2–COOH +


12. 1º and 2º amine can be differentiated by Carbylamine test.

13. Aromatic 1º amine gives positive azo dye test.

OH

COOH
O / Zn
14. 
3


15. Lucas reagent is used to distinguish alcohol and phenol.

16. CH3–CH2–NH2 + CHCl3 + KOH  CH3CH2NC

CH3–CO–CH3 + Ca(OCl)2  CHCl3 + (CH3COO)2Ca

17. Amines give positive Hinsberg test.

18. Acetaldehyde and Propyne can be distinguish by tollen's reagent and Iodoform test.

21.

22. ,

H / Ni Cl / h
23. 
2
 
2
 +

24. C5H8 , (Molecular Mass = 68)

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Structure Identification & POC

PART - II
1. If nitrogen is present in organic compound, then sodium extract contains Na 4 [Fe(CN)6]
fuse
Na + C + N   NaCN
FeSO4 + 6NaCN  Na4[Fe(CN)6] + Na2SO4
(A)
A changes to prussian blue Fe4[Fe(CN)6]3 on reaction with FeCl3
4FeCl3 + 3Na4[Fe(CN)6  Fe4[Fe(CN)6]3 + 12 NaCl

2. 2,3-Dimethylbutane has two chemically different hydrogen atoms so it can give two monochlorinated
structural compounds.

3. Neutral FeCl3 reacts with phenol and give violet coloured complex.

4.

5. single product.

6. isobutyl alcohol doesn't give positive iodoform test.

7.

8. Mass of organic compound = 1.4 g

let it contain x mmole of N atom.
organic compound  NH3
x m mole
2NH3 + H2SO4  (NH4)2SO4. (1st)
6 mmole
initially taken.
H2SO4 + 2NaOH  Na2SO4 + 2H2O (2nd)
2 mmole
reacted
Hence m moles of H2SO4 reacted in 2nd equation = 1
 m moles of H2SO4 reacted from 1st equation = 6 – 1 = 5 m moles
 m moles of NH3 in 1st equation = 2 × 5 = 10 m moles
 m moles of N atom in the organic compound = 10 m moles
 mass of N = 10 × 10–3 × 14 = 0.14 g
0.14
% of N = × 100 = 10 %
1.4

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Structure Identification & POC

Atomic mass of Br Wt. of AgBr

9. %X= × × 100
Molecular mass of AgBr Wt. of organic Bromide
80 141
Thus % Br = × × 100 = 24
188 250

10.  (5-keto-2-methyl hexanal)

11. Nitrogen in aniline is estimated by Kjeldahl's method.

PART - IV
1. The given compound gives Tollen’s reagent and 2,4-DNP test i.e. the compound is aldehyde. Further it
gives no Iodoform test. From the given molecular formula C8H8O is expected. Therefore the correct
answer is (C).

O3
2.  
Oxidation

O / Zn
3. 
3
 2-methylpentanedial+4-oxopentanal+formaldehyde+acetone.

4. CH3–CH–CH=CH2 gives bromine water test, Lucas reagent test and haloform test.
OH

5.

(I) gives immediate turbidity by Lucas reagent and (II) does not give turbidity appriciably.

6. Terminal alkyne and –CH=O group gives positive test with tollens reagent.

7. 2H / Ni
 
C  CH H2 / Ni
CH2 – CH3
|   | 3 monochloro product
HC  C – CH – C  CH H3C – CH2 – CH – CH2 – CH3
Both structures give three monochloro structural isomeric products.

Na
8. C3H4  CH3–C C–H CH –C C Na + ½H2
3

Br 2 + H2O
+ve
Bayer's Reagent +ve
Cu2Cl2 + NH4OH
+ve
AgNO3 + NH4OH
+ve

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Structure Identification & POC

9. CH3–O–CC–H gives white precipitate with tollen’s reagent and Liberates H2 gas with Na metal.
CH3
|
CH3  C  CH2  O  CH3 gives instant turbidity with anhydrous ZnCl2/HCl and Liberates half mole H2
|
OH
gas with sodium metal.

H / Ni Cl / h
10. X= 
2
 
2
 3 structural products

11. CnH2nO2 = 172

 n = 10
OH
[I]
 COOH +
P + H3O+

[II] COOH +
HO

[III] COOH +
HO

CH3 CH3

12. CH3 –C=CH–CH3 CH3 –CH–CH=CH2

CH3 CH3 CH3
CH3–CH–C CH H2C =C–C=CH2 CH3 –C=C=CH2

13. CH3–C–CH2–CH2–CH2–CH3 CH3–C–CH–CH2–CH3

O O CH3
CH3
CH3–C–CH2–CH–CH3 CH3–C–C–CH3
O CH3 O CH3

14. Na Metal, HCl+ZnCl2, FeCl3, NaOH+Phenolpthalein, dill.KMnO4, Br2/H2O gives positive test with
ascorbic acid.

15. Compound (I), (IV), (V), (VII) and (IX) gives positive haloform compound (III), (VII) and (IX) gives
positive Lucas reagent, x = 5, y = 3 so, (5 + 3) = 8.

16. Only one alkene

Three monochloro isomers are possible as it has three different types of 'H' atoms.

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Structure Identification & POC

17. DU  1, must be acid  C5H11–COOH 8 isomers

18. (NH4)3PO4.12MoO3

19. Cysteine, Methionine, Diethylthioether, Ethylmercaptan

reductive
20.  O+O O + H–C–H
ozonolysis
O

CH3 reductive
21. C C  CH3 –C–H + CO2 + OHC–C–CHO
H ozonolysis
O O

 2HCHO + H–C–C–CH2–C–H + H–C–CH2–C–CH2–C–H

reductive
22.
ozonolysis
O O O O O O

(23-24) (P) = (Q) = (R) =

O O O
(P) & (R) can decolorize bromine water.
(R) can answer Tollen’s reagent test but (P) cannot.
There is no aromatic ring is any of the structures.

25. Due to unsaturation brown colour of Br2/H2O decolourises. Carboxylic acid gives CO 2 gas with
NaHCO3. Aldehydes gives black or silver ppt. with Tollen's reagent and terminal alkyne gives white ppt.
with tollen's reagent. group gives positive 2,4-DNP test.

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