SELF ASSESSMENT TEST

Time : 50 Min Max. Marks: 90

INSTRUCTIONS
Q.1 to Q.30 have one or more than one correct alternative(s) and carry 3 marks each.
There is NEGATIVE marking and 1 mark will be deducted for each wrong answer.
Q.1 Pick an ether which can be prepared by direct Williamson's synthesis.
(A) CH3CH2CH2–O–CH2CH2CH3 (B) Ph–O–CH2CH3
(C) (CH3)3C–O–C2H5 (D) CH3CH=CH–O–CH=CH2

Q.2 The given product can not be formed by which set of reactants in the presence of AlCl 3 catalyst.

(A) + Cl – (B) –Cl +

(C) + CH3Cl (D) + CH3Cl

Q.3 The final major product of the following reaction is

conc. H SO ( CH 3CO ) 2 O KMnO / OH —

 24  A    B  4 
 C
BF3 

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

Organic Chemistry [9]

 Question No. 4 to 6 (3 questions)
A research scholar synthesised the compound A in the laboratory

A:

He wanted to study this compound in acidic medium and kept for some time in it. After an hour,
when isolated the compound, to his surprise, he got the mixture of two compounds B, C. He
studied their properties and compared them with A.
A B C
reaction with HaHCO 3 brisk effervescence no no
blue litmus red no no
NaOI no no yellow ppt.
[Ag(NH3) 2 ] no no silver - mirror
A  B  C carbon  54.55% ,
H 3O 
clue original
hydrogen  9.1%
Q.4 B formed is

(A) (B) (C) (D) none

Q.5 Compound C is
O
||
(A) CH 3CCH 3 (B) CH3CH2CHO (C) HCHO (D) CH3CHO
Q.6 B is formed due to
(A) cleavage of C–O bond followed by esterification between –COOH and –OH present.
(B) decarboxylation of –COOH group
(C) oxidation of –CH2COOH into –COOH
(D) none
HI
 A
Q.7
conc
 . HI
 B
A & B are respectively:

(A) & (B) &

(C) Both (D) Both

Q.8 An aromatic electrophilic substitution reaction with NaNO 2 / HCl will be observed in

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

Q.9 Which of the following will give a product with phenolic group on heating
(A) Phenyl propyl ether (B) Phenyl allyl ether
(C) Phenyl crotyl ether (D) Phenyl venyl ether
Organic Chemistry [10]
Q.10 Questions given below consist of two statements each printed as Assertion (A) and Reason (R); while
answering these questions you are required to choose any one of the following four responses:
(A) if both (A) and (R) are true and (R) is the correct explanation of (A)
(B) if both (A) and (R) are true but (R) is not correct explanation of (A)
(C) if (A) is true but (R) is false
(D) if (A) is false and (R) is true
Assertion : Two products, alkyl cyanide and alkyl isocyanide are obtained during the reaction of
alkyl halides with KCN. Order of cyanide isocyanide ratio is : 1°>2°>3°.
Reason : 3° alkyl halide undergo SN1 reaction which is non selective with respect to nucleophile
strength.
Q.11 Select true statement(s)
(A) Every alcohol which gives red colour during Victor Meyor test will give turbidity only on
heating with Lucas reagent.
(B) Propanol and isopropanol can be differentiated by idoform test.
(C) Butanol and isobutanol can be differentiated by Lucas test.
(D) Both iso-pentyl alcohol and neopentyl alcohol give product with same functional group with
HKMnO4
Q.12 In the reaction,
O
|| Base
+ CH2 = CH  C  CH 3 


how is the product formed?

(A) Micheal addition followed by aldol condensation
(B) Aldol condensation followed by Micheal addition
(C) Mannich reaction
(D) Knoevenagel reaction followed by aldol condensation
Q.13 Which are correct statements:
(A) Cannizzaro reaction is hydride transfer reaction
(B) Hofmann-degradation of acid amide involves intramolecular migration of alkyl / aryl group
from C toN
(C) Fries migration is intramolecular
(D) Cannizzaro reaction is disproportionation reaction
Q.14 Which is / are true statements:
(A) CH 2  CH 2  COOH on heating is converted into CH2 = CHCOOH
|
NH 2

(B) CH 2  CH 2  CH 2COOH on heating is converted into

|
OH

(C) CH 2 COOH on heating forms

|
OH
(D) CH 2 COOH forms Zwitter ion which moves towards cathode at pH = 4.
|
NH 2

Organic Chemistry [11]

 H 2O
Q.15 PhMgBr + 2PhCHO 
 A   B
B is
(A) Ph2CH–OH (B) Ph3C–OH (C) PhCH2–OH (D) Ph–OH
O
|| 
Q.16 Me  C  O  CH 2  CH 2  N H 3 NaOH
 Q
Q is:
O O
|| ||
(A) Me  C  O  CH 2  CH 2  NH 2 (B) Me  C  NH  CH 2  CH 2  OH

(C) (D) MeCOONa + HOCH2CH2NH2

Q.17 How many asymmetric carbon atoms are present in the following compound Coccinellin?

Coccinellin
(A) 2 (B) 3 (C) 4 (D) 6
Q.18 Which one of the following is non-reducing sugar?
(A) Glucose (B) Arabinose (C) Fructose (D) Sucrose
Q.19 Which of the following molecules is capable of forming Zwitter ion?
(A) CH3–CHOH–NH2 (B) NH2–CH2–COOH
(C) CH3–COOH (D) CCl3–NO2
Q.20 Which of the following option is correct? Where a, b, c, d are positions of electrophilic attack.
Nf = Not favourable; f = favourable (for electrophilic attack)

(A) (B)

(C) (D) All


Q.21 +O=S H
 X + Me2S

Structure of X is
OH OH CHO CH 2  CH 3
| | |
(A) HO–CH2–CHO (B) CH 2  CH 2 (C) CHO (D) |
OH

Organic Chemistry [12]

Q.22 Identify (X) of the following reaction:

Caro
 's acid

 (X)

(A) (B)

(C) (D)

Q.23 is converted into by

(A) (i) KMnO4(ii) H+;  (B) (i) Na2Cr2O7, H+ (ii) H+ ; 

(C) (i) Ag(NH3)2+ (ii) H+ ;  (D) All of these

Q.24 OH

 Olefinic product.


Identify major product

(A) (B) (C) (D) None of these

O
|| conc. H SO
Q.25 Ph 3C  C  OH  24  (A)
MeOH
A is:
O O
||  
||
(A) Ph 3C  C  OMe (B) Ph 3C  O Me (C) Ph 3C  O H (D) Ph  C  Ph

Q.26 An alkene cnH2n is converted by a reduction procedure to cnH2n +2. The % change in the molecular
weight = 3.57. What is the value of n?
(A) 2 (B) 3 (C) 4 (D) 5

Organic Chemistry [13]

Q.27 The product expected from the reaction

CHO
|
CH 2
|
CHOH HIO
4 
| excess
CHOH
|
CH 2OH

O
||
(A) H  C  CH 2  CHO  HCOOH  HCHO
(B) HOOC–CHOH–CHOH–COOH+HCOOH
(C) HOOC–CH 2CH2COOH + HCOOH + HCHO
(D) HOOC – COOH + HCOOH + HCHO

Q.28 Column I (reaction) Column II (name of the reaction)

(A) 2C6H5CHO 20
%NaOH

 (P) Benzoin condensation
(B) C6H5CHO + HCHO 20
%NaOH

 (Q) Cannizzaro reaction
(C) 2C6H5CHO KCN

/ C 2 H 5OH
 (R) Cross cannizzaro reaction
CH COONa
(D) C6H5CHO + (CH3CO)2O 3  (S) Perkin reaction


Q.29 Column I (reaction) Column II (reagent)

(A) Wolf-kishner reduction (P) NaCN /C 2H5OH
(B) Witting reaction (Q) (C6H5)3P = CH2
(C) Benzoin condensation (R) conc. NaOH
(D) Cannizzaro reaction (S) NH2NH2/KOH

Q.30 Column I (compound) Column II (pka)

O
||
(A) CH 3  C  CH 2  COOC 2 H 5 (P) 17

O O
|| ||
(B) CH 3  C  CH 2  C  CH 3 (Q) 8.9
(C) CHO–CH2–CHO (R) 10.7
(D) CH3–CHO (S) 5

Organic Chemistry [14]