TOPIC WISE REVIEW CPP-II-GOC&EAS

Q.1 In each of the following pairs, determine whether the two represent resonance forms of a single species
or depict different substances. If two strictures are not resonance froms, explain why.
(a) and
(b) and
(c) and

Q.2 Match each alkene with the appropriate heat of combustion:

Heats of combustion (kJ/mol) : 5293 ; 4658; 4650; 4638; 4632
(a) 1-Heptene (b) 2,4-Dimethyl-1-pentene
(c) 2,4-Dimethyl-2-pentene (d) (Z)-4,4-Dimethyl-2-pentene
(e) 2,4,4-Trimethyl-2-pentene

Q.3 Choose the more stable alkene in each of the following pairs. Explain your reasoning.
(a) 1-Methylcyclohexene or 3-methylcyclohexene
(b) Isopropenylcyclopentane or allylcyclopentane

(c) or

(d) (Z)-Cyclononene or (E)-cyclononene

(e) (Z)-Cyclooctadecene or (E)-cyclooctadecene

Q.4 Rank the following sets of intermediates in increasing order of their stability giving appropriate reasons
for your choice.
(a) C 6 H 5 , p  NO 2 (C 6 H 4 )  , p  CH 3  (C 6 H 4 )  , p  Cl  C 6 H 4

(b)

Q.5 For the following compounds, arrange the labelled proton in increasing order of their ease of
deprotonation.

Q.6 In each of the following pairs of ions which ion is more stable:
 
(a) (I) C6H5– CH 2 and (II) CH2=CH– CH 2
 
(b) (I) CH3– CH 2 and (II) CH2 = CH

(c) (I) and

 (d) (I) CH 3  CH  CH 3 and CH 3  N  CH 3
| |
CH 3  C  CH 3 CH 3  C  CH 3
 
Q.7 Consider the given reaction:

+ 3H2 Pd /C
 

In the above reaction which one of the given ring will undergo reduction?

Q.8 In which of the following molecules resonance takes place through out the entire system.

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

COOCH 3
(e) | (f)
COOCH 3
Q.9 Which of the following groups cannot participate in resonance with other suitable group :
— 
(a) – COOH (b)  CO O (c) – COCl (d)  NH 3
  
(e)  C H 2 (f)  C H 2 (g) CH 2  N 
|
CH 3
Q.10 Which of the following group can participate in resonance with other suitable group :
 — 
(a) CH 2  O  (b)  CH 2  C H 2 (c)  CH  C H2 (d)
2


(e) (f) – BH2 (g)  P Ph 3

Q.11 Write the resonance hybrid of each of the following :

— 
(a) CH 2  CH  C H 2 (b) (c) (d) CH 2  CH  C H 2

(e) CH2 = CH – CH2

Q.12 In which of the following molecules  – electron density in ring is maximum :

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

Q.13 Which of the following pairs has higher resonance energy :


(a) CH3COOH and CH3COONa (b) CH2 = CH – O and CH2 = CH – OH

(c) and (d) and

(e) and CH2 = CH – CH = CH – CH = CH2

Q.14 In the reaction sequence

OH O
| ||
C 6 H 5  CH  CH 2  C  CH 3 (
i ) NaOBr
 product
( ii ) H 2 O / H 
( iii ) 
product will be
OH
|
(A) C 6 H 5  CH  CH 2  COOH (B) C6H5–COOH, COOH–COOH and CHBr3

O
||
(C) C 6 H 5  C  CH 3 , CO2 and CHBr3 (D) Only CHBr3

Q.15 Which of the following has minimum reactivity towards nucleophiles?

O O
|| ||
(A) CH2O (B) CH3CHO (C) CH 3  C  CH 3 (D) CH 3  C  CH 2  CH 3

Q.16 and

Are which type of isomers

(A) Chain (B) Position (C) Metamerism (D) functional

Q.17 Which of the following carbocation is most stable?

(A) (B)

(C) (D)
Q.18 Which of the following alcohol shows fastest reaction with HI ?

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

Q.19 Among the foloowing pairs in which case the second compound has higher heat of hydrogenation.

(A) , (B) Cis-2-butene, trans-2-butene

(C) , (D) 1-butene, 2-butene

Q.20 CH3CH2NO2 will not show...... isomerism:

(A) Chain (B) functional (C) tautomerism (D) geometrical
Q.21 In which of following compound chiral center is not affected on heating.
(A) CH 3  CH  COOH (B)
|
OH
(C) CH 3  CH  CH 2  COOH (D) CH 3  CHCOOH
| |
OH CH 2COOH

Q.22 3 H O
 

products can be: (Both stable & unstable form)

(A) CH3CH(OH)2, CH3CH(OH)COOH (B) CH3CHO, CH3CH(OH)COOH
(C) CH3CH2COOH, CH3CH2OH (D) CH3CH(OH)COOH, CH3CH2OH
Q.23 Which of the following compounds yield most stable carbanion after rupture of (C1–C2) bond:
O O O
|| || ||
(A) CH 3  C  CCl 3 (B) CH 3  C  CBr 3 (C) CH 3  CH 2  C  CI 3 (D) none of these
1 2 1 2 1 2
Q.24 Products formed when HCl adds to 2,4- hexadiene is:
(A) 4-chloro-2-hexene (B) 2-chloro-3-hexene
(C) 2-chloro-4-hexene (D) 1-chloro-2-hexene
Q.25 Which species is not aromatic?

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

Q.26 Aromatic character is possible only when

(A) six electrons are delocalized
(B) the molecule is cyclic and planar having delocalized (4n +2) electrons where n = 1,2,3....
(C) alternate sigma () & pie () bond are present.
(D) None is true
Q.27 (i)Choose the member of the following pairs of unsaturated hydrocarbons that is more reactive towards
acid-catalysed hydration and predict the regiochemistry of the alcohols formed from thi s compound.

(a) or (b) or

(c) or

Q.28 The reaction of cyclopentyl bromide with sodium cyanide to give cyclopentyl cyanide

NaCN

ethanol  water

Cyclopentyl bromide Cyclopentyl cyanide

proceeds faster if a small amount of sodium iodide is added to the reaction mixture. Can you suggest
a reasonable mechanism to explain the catalytic function of sodium iodide?
Q.29 When ethyl bromide is added to potassium t-butoxide, the product is ethyl t-butyl ether.
CH3CH2 – Br + (CH3)3C – O– +K  (CH3)3C – O – CH2CH3
ethyl bromide potassium t-butoxide ethyl t-butyl ether
(a) What happens to the reaction rate if the concentration of ethyl bromide is doubled ?
(b) What happens to the rate if the concentration of potassium t-butoxide id tripled and the concentration
of ethyl bromide is doubled ?
(c) What happens to the rate if the temperature is raised ?
Q.30 Solution A was prepared by dissolving potassium acetate in methanol Solution B was prepared by
adding potassium methoxide to acetic acid. Reaction of methyl iodide either with solution A or with
solution B gave the same major product. Why ? What was this product?
Q.31 Outline an efficient synthesis of each of the following compounds from the indicated starting material
and any necessary organic or inorganic reagents :
(a) Cyclopentyl cyanide from cyclopentane.
(b) Cyclopentyl cyanide from cyclopentene.
(c) Cyclopentyl cyanide from cyclopentanol.
(d) Isobutyl iodide from isobutyl chloride.
(e) Isobutyl iodide from tert-butyl chloride.
(f) Isobutyl azide from isopropyl alcohol
Q.32 Choose the compound of molecular formula C7H13Br that gives each alkene shown as the exclusive
product of E2 elimination.

(a) (b) (c)

(d) (e) CH = CH2 (f)

(g) C(CH3)3
Q.33 Write the structure of the principal organic product to be expected from the reaction of 1-bromopropane
with each of the following :
(a) Sodium iodide in acetone.
O
||
(b) Sodium acetate ( CH 3CONa ) in acetic acid.
(c) Sodium ethoxide in ethanol.
(d) Sodium cyanide in dimethyl sulfoxide.
(e) Sodium azide in aqueous ethanol
(f) Sodium hydrogen sulfide in ethanol
(g) Sodium methanethiolate (NaSCH3) in ethanol.
Q.34 Complete the following reactions. Give all possible products in each case. Give mechanism of the
reactions.

HOH / 
(a) Moist
 Ag 2O
  (b) CH2 – Cl  

Q.35 Complete the following reactions :

O O
|| ||
i ) I 2 / NaOH / 
(a) CH 3  C  (CH 2 ) 4  C  CH 3 (   (A)  (B)
( ii ) H 

O
||
(b) C  CH 3 (
i ) Br2 / NaOH
  
(C)  (D)
( ii ) H

(c) CHOH – CH3 (

i ) CaOCl 2 / HOH
    (E) + (F)
( ii ) H
NaOH / F2
(d) CH 3  CH  CH 2  CH 3   G + H
|
Cl
Q.36 Complete the following reactions

(a) C6 H 5  CH  CH 3  NaCl  HOH Electrolys

  is
 A sweet smelling liquid
|
Br

(b) C6H5 – aq

. NaOH


O
||
( i ) CH 3 C  CH 3
Q.37 CH 3 CH 2 CH 2 Cl alc
. KOH
 A SO
2Cl 2
 B Mg
 /
Et 2O
 C     D
( ii ) aq. NH 4 Cl

/
H2SO
4   E.

Q.38 Give the product of reaction of each of the following with excess phenylmagnesium bromide followed
by acid hydrolysis:
 (a) (b) (c) (d)
(e) C6H5–CN
Q.39 (a) Which compound will give Walden Inversion in SN2 reaction?
(A) CH3–CH2–Br (B) Ch3–CHD–Br (C) CH3–Br (D) C6H5–CH2–CH2Cl

(b) Which among the following will give SN1 reaction?

(A) (B) (C) CH3–CH2–I (D)

Q.40 Which of the following is not the property of benzene:

(A) Characteristic smell (B) Inflammable
(C) Unsaturation (D) Colourless
Q.41 Which of the following reagents and conditions convert benzene to chloro-benzene:
(A) Cl2, sunlight, heat (B) HCl, heat (C) HCl, sunlight, heat (D) Cl2, AlCl3, cold

Q.42 Ethylbenzene + Cl2 Light

 (main) compound is:
(A) o-& p-chloroethylbenzene (B) 1-Chloroethylbenzene
(C) 2-Chloroethylbenzene (D) m-Chloroethylbenzene
Q.43 p-Nitrotoluene on further nitration gives:

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

Q.44 Which of the following substituted benzene derivatives would furnish three isomers in significant amount
when one more substituent is introduced:

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

Q.45 Which of the following carbocations is expected to be most stable?

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

Q.46 For the electrophilic substitution reaction involving sulphonation, which of the following sequence
regarding the rate of reaction is true?
(A) k C6 H6 > k C6 D6 > k C6 T6 (B) k C6 H6 < k C6 D6 < k C6 T6

(C) k C6 H6 = k C6 D6 = k C6 T6 (D) k C6 H6 > k C6 D6 < k C6 T6

Q.47 Match the following:
Column I Column II

(A) CO2is evolved from (P)

NaHCO3 by the reaction of

(B) Libermann nitroso test is given by (Q)

(C) Compounds gives yellow oily (R)

liquid on reaction with NaNO2 + HCl

(D) Compounds evolve a colourless gas (S)

on reaction with active metals

Q.48 Write the principal organic product in each of the following reactions:

H NNH
(i) + C6H5CH2SK  A (ii) 2 2  B
triethylene
glycol

( i ) HNO , H SO
3 2 (i) NaNO , HBr
(iii)    4  D (iv)   2   E
( ii ) NaOCH 3 ,CH 3OH ( ii ) CuBr

( i ) NBS, Benzoyl peroxide ,CCl , heat

(v) 4
          F
( ii ) NaSCH 3

(vi) + CH3CH2ONa  G (vii) + C6H5CH2SNa  H

(viii)
NaOCH
 3  I (ix) + Mg
,THF

CH 3OH heat
Q.49 Suggest a reasonable mechanism for each of the following reactions:
( i ) Excess NaNH , NH
(a) C6H5Br + CH2(COOCH2CH3)2     
2
2  C6H5CH(COOCH2CH3)2
( ii ) H 2O

( i ) Excess NaNH , NH
2
     3 
(b) ( ii ) H 2O

NaNH
2 
 
(c) ether

K CO
(d) 2 
3 
heat

Q.50 Say which pka belong to which functional group in case of following amino acids :

(i) cysteine : 1.8, 8.3 & 10.8

(ii) glutamic acid : : 2.19, 4.25, 9.67

Q.51 Record the following sets of compounds according to increasing pKa ( = – log Ka)

(a) , , cyclohexane carboxylic acid. (b) 1-butyne, 1-butene, butane

(c) Propanoic acid, 3-bromopropanoic acid, 2-nitropropanoic acid

(d) Phenol,o-nitrophenol, o-cresol (e) Hexylamine, aniline, methylamine
Q.52 Explain which compound is the weaker base.

(a) or (b) CH2 = CH – CH = CH – CH2– or CH2 = CH – CH2–

O O O O
|| || || ||
(c) O   C  C  OH or HO  C  C  OH (d) or
Q.53 Rank the following amines in increasing basic nature.

(a)

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

(b)

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

(c)

(i) (ii) (iii)

Q.54 Arrange the basic strength of the following compounds.
(a) OH– CH3COO– Cl–
(i) (ii) (iii)
(b) CH  C– CH2 = CH– CH3 CH2 –
(i) (ii) (iii)
(c) CH2 = CHCH2NH2 CH3CH2 CH2NH2 CH  C – CH2NH2
(i) (ii) (iii)

(d)

(i) (ii) (iii)

Q.55 Set the following in increasing order of pka :
(i) Methane sulfonic acid, acetic acid & methanol.
(ii) CH3– CH2 – CH3 , CH2 = CH – CH3 , CH3 – CHO , CHO – CH2 – CHO , CH4
(iii) CH3NO2 , (NO2)2 – CH2 , (NO2)3 – CH

(iv) , , ,

(v) CH3COOH , NO2– CH2 – COOH , CH 3  C  CH 2  C  OH

|| ||
O O

(vi) , ,

H H H H
(vii) CHO – CH2 – CHO , CH 3  C  CH 2  C  CH 3 , Et  O  C  CH 2  C  O  Et ,
|| || || ||
O O O O

Et  O  C  CH 2  C  CH 3
|| ||
O O
Q.56 Cyanic acid (HO–CN) & isocyanic acid (H–N=C=O) differ in the positions of their electrons but
their structure do not represent resonance structures.
(a) Explain
(b) Loss of a proton from cyanic acid yields the same anion as that obtained by loss of a proton from
isocyanic acid. Explain.

(e)

(i) (ii) (iii)

(f) Cl– RCOO– OH– RO– NH2 –
(i) (ii) (iii) (iv) (v)
Q.57 Set the following in increasing order of pkb :
(i) CH3NH2 , (CH3)2 NH , (CH3)3 N , NH3 [In aqeous medium]

(ii) , (iii) ,

Q.58 Which of the following would you predict to be the stronger acid ?

(a) or

(b) CH3 – CH2 – CH2 – OH or CH3 – CH = CH – OH

(c) CH3 – CH = CH – CH2 – OH or CH3 – CH = CH – OH

Q.59 The Ka of phenylacetic acid is 5.2 × 10–5, and the pKa of propionic acid is 4.87.

(a) Calculate the pKa of phenylacetic acid and the Ka of propionic acid.
(b) Which of these is the stronger acid?
(c) Predict whether the following equilibrium will favor the reactants or the products.
Q.60 In each of the following pairs which is less stable :

(a) l (b) l

(c) l (d) l

(e) l

Q.61 In each of the following pairs which will have higher enol content :

(a) CH 2  CHO and CH 2  CHO (b) and

| |
NO 2 Cl

(c) and

(d) and

Q.62 Draw enol forms of these carbonyl compounds and comment on the stability of the enol forms.

(a) (b)
 ANSWER HINT SOLUTION

Q.1 (a) are resonance form

Q.2 (a) 4658, (b) 4638, (c) 4632, (d) 4656, (e) 5293
Q.3 (a) i , (b) i , (c) ii, (d) i, (e) ii
Q.4 (a) ii < iv < i < iii, (b) iii < ii < i
Q.5 1<2<3
Q.6 (a) I, (b) I, (c) II, (d) II
Q.7 A
Q.8 (b), (c) Q.9 (d) Q.10 (a), (e), (f), (g)
Q.11 ?
Q.12 B
Q.13 (a) II, (b) I, (c) I, (d) I, (e) I
Q.14 C
Q.15 D
Q.16 D
Q.17 C
Q.18 B
Q.19 C
Q.20 A,D
Q.21 A,B,D
Q.22 A,B
Q.23 A
Q.24 A,B
Q.25 B
Q.26 D
Q.27 (i) (a) II, (b) I, (c) II
28. ?
29. ?
Q.30 MeCOOMe
31. ?

Q.32 (a) ; (b) ; (c) ; (d) ; (e)

(f) , (g)

Q.33 (a) ; (b) ; (c) ; (d) ; (e) ; (f) ; (g)

34. ?
Q.35 (a) CHI 3 +(CH2 )4(COOH)2 , (b) CHBr 3+ , (c) CHCl3 + , (d) CHF3 +
EtCOONa

Q.36 (a) CHCl3, (b) PhCHO

Q.37 Me2C=CH–CH=CH2
38. ?
39. ?
Q.40 C
Q.41 D
Q.42 B
Q.43 A
Q.44 C
Q.45 D
Q.46 A
Q.47 (A) Q, (B) P,R,S, (C) R,S, (D) P,Q,R,S

Q.48 (i) (ii) (iii) (iv)

(v) (vi) (vii) (viii)

(ix)

49.

Q.50 (i) cysteine : (ii) glutamic acid :

Q.51 (a) 2; (b) 1; (c) 2; (d) 2

Q.52 (a) 3<2<1<4; (b) 1<2<3<4; (c) 3<1<2
Q.53 (a) 1>2>3; (b) 1<2<3; (c) 3<1<2; (d) 2<1<3; (e) 1<2<3; (f) 1<2<3<4<5
Q.54 (i) 1<2<3; (ii) 1>5>2>3>4; (iii) 1>2>3; (iv) 1>3>4>2; (v) 1>3>2; (vi) 2>1>3;
(vii) 3>4>2>1
55.
Q.56 (i) 4>3>1>2; (ii) 1<2; (iii) 1<2
Q.57 (a) 1<2<3; (b) 3>1>2; (c) 1<3<2
Q.58 (a) 2; (b) 2; (c) 2
Q.59 (a) 4.25, (b) 1.34×10–5, (c) reactant
Q.60 (a)2; (b) 2; (c) 2; (d) 2; (e) 1
Q.61 (a) 1; (b) 1; (c) 1; (d) 1

Q.62 (a) (b) both are more stable