1.

The reaction of CçH,CH=CHCH, with HBr

produces
(a) CçH,CH,CH,CH,Br

CH=CHCH,
(b) (c) CoH,CHCH,CH,
Br
Br

() CH,CH,CHCH, (2015, Cancelled)

Br

2. In the replacement reaction

C+MF ’CF+MI
The reaction will be most favourable if M happens to
be
(a) Na (b) K
(c) Rb (d) Li (Mains 2012)
3. When chlorine is passed through propene at 400°C,
which of the following is formed?
(a) PVC
(b) Allyl chloride
(c) Propyl chloride
(d) 1,2-Dichloroethane (1993)
4. Elimination reaction of 2-bromopentane to form
pent-2-ene is
(A)B-Elimination reaction
(B) Follows Zaitsev rule
(C) Dehydrohalogenation reaction
(D) Dehydration reaction
(a) (A), (B), (C) (b) (A), (C), (D)
(c) (B), (C), (D) (d) (A), (B), (D)
(NEET 2020)

5. The hydrolysis reaction that takes place at the

slowest rate, among the following is

(a) -Cl aq.NaOH -ÕNa

CH, CH,
aq. NaOH
(b) H,C--CH,-CI > H,CCH OH
(c) H,C=CH-CH,CI-OH
H,C=CH-CH,OH
(d) -CH,C|49NaoH, CH,OH
(Odisha NEET 2019)
6. The compound A on treatment with Na gives B, and
with PCl, gives C. B and C react together to give
diethyl ether. A, B and Care in the order
(a) C,H,OH, C,H, C,H,CI
(b) C,H,0H,C,H,CI, C,H,ONa
(c) C,H,C, C,H, C,H,OH
(d) C,H,OH, C,H,ONa, CH,CI (NEET 2018)
7. The compound C7Hg undergoes the following
reactions :
3Cl,/A Br, /Fe ’B Zn/HCI
C,Hg
The product C is
(a) m-bromotoluene
(b) o-bromotoluene
(c) 3-bromo-2,4,6-trichlorotoluene
(d) p-bromotoluene. (NEET 2018)
8. Identify A and predict the type of reaction.
OCH,
NaNH,

Br
OCH,
NH, and elimination
(a) addition reaction

OCH,
Br
and cine substitution
(b) reaction

OCH,
and cine substitution
(c)

OCH3
and substitution
(d) reaction (NEET 2017)
NH,
9. Consider the reaction,
CH,CH,CH,Br + NaCN
CH,CH,CH,CN + NaBr
This reaction will be the fastest in
(a) ethanol
(b) methanol
(c) N,N-dimethylformamide (DMF)
(d) water. (NEET-II 2016)
10. Which of the following biphenyls is optically active?

(a)

CH,

(b)

CH,
O,N
(c)

Br Br

(d) (NEET-I 2016)

11. For the following reactions :
(A)CH,CH,CH,Br + KOH
CH,CH =CH, + KBr + H,O
(B)"CH, + KOH
Br
HyC CH,
+ KBr
OH

Br
(C) + Brz
Br
Which of the following statements is correct?
(a) (A) is elimination, (B) and (C) are substitution
reactions.
(b) (A) is substitution, (B) and (C) are addition
reactions.
(c) (A) and (B)are elimination reactions and (C) is
addition reaction.
(d) (A)is elimination, (B) is substitution and (C) is
addition reaction. (NEET-I 2016)
12. Twopossible stereo-structuresofCH,CHOHCOOH,
which are optically active, are called
(a) atropisomers (b) enantiomers
(c) mesomers (d) diastereomers. (2015)
13. In an Syl reaction on chiral centres, there is
(a) inversion more than retention leading to partial
racemisation
(b) 100% retention
(c) 100% inversion
(d) 100% racemisation. (2015)
14. Which of the following compounds will undergo
racemisation when solution of KOH hydrolyses?
CH,CI
(1) (ü) CH,CH,CH,C1

CH, ÇH,
(iiü) H,C-CH-CH,CI (iv) HYC
H
C,Hs
(a) (i) and (ii) (b) (ii) and (iv)
(c) (ii) and (iv) (d) (i) and (iv)
(2014)
15. Given:
Br
H Br H Br
CH3 and
H
H CH, CH,CH,
Br
II
Iand IIare
(a) identical
(b) a pair of conformers
(c) a pair of geometrical isomers
(d) a pair of optical isomers.
(Karnataka NEET 2013)
16. Which of thefollowing acids does not exhibit optical
isomerism?
(a) Maleic acid (b) a-Amino acids
(c) Lactic acid cid
(d) Tartaric acid (2012)
17. Consider the reactions :
CoHOH
(i) (CH,),CH CH,Br
(CH,),CH - CH,0C,H, + HBr
(ii) (CH,),CH - CH,Br C,H;0
(CH;),CH-CH,OC,H, + Br
The mechanisms of reactions (i) and (iü)
respectively
(a) Syl and S2 (b) Syl and Sl
(c) SE2 and SE2 (d) SE2 and S1
(Mains 2011)
18. Which of the following compounds undergoes
nucleophilic substitution reaction most easily?
CI
Cl
(a) (b)
NO,
CH,
CI
CI
(c) (d)|

OCH, (Mains 2011)

19. Which one is most reactive towards Sy1 reaction?
(a) CçH,CH(C,H,)Br
(b) CH,CH(CH})Br
(c) CoH,C(CH,)(C,H,)Br
(d) CçH,CH,Br (2010)
20. The correct order of increasing reactivity of
X X

NO2

NO2
I II

(CH3),C-X (CH3),CHX
II IV

C-X bond towards nucleophile in the following

compounds is
(a) I<II < IV<III (b) II< III <I<IV
(c) IV <III<I<II (d) III< II<I<IV
(2010)
21. In the following reaction,
1. Mg, Ether
CeH;CH,Br 2. H,0+
’X,

the product 'X is

(a) CçH,CH,0CH,C,H,
(b) CçH,CH,OH
(c) CçH,CH,
(d) CçH,CH,CH,C,H, (Mains 2010)

22. Which of the following reactions is an example of

nucleophilic substitution reaction?
(a) 2RX+ 2Na ’R-R+ 2NaX
(b) RX + H, ’ RH + HX
(c) RX + Mg> RMgX
(d) RX+ KOH >ROH + KX (2009)
23. How many stereoisomers does this molecule have?
CH,CH =CHCH,CHBrCH,
(a) 8 (b) 2
(c) 4 (d) 6 (2008)
24. In a Sy2 substitution reaction of the type
DMF
R-Br + Cl ’ R-Cl + Br
which one of the following has the highest relative
rate?

CH,
(a) CH,-Ç-CH,Br (6) CH,CH,Br
CH,
(c) CH,CH,CH,Br (4) CH,-ÇH-CH,Br
CH3 (2008)
25. If there is no rotation of plane polarised light bya
compound in a specific solvent, though to be chiral,
1t may mean that
(a) the compound is certainly mes
(b) there is no compound in the solvent
(c) the compound may be a racemic mixture
(d) the compound is certainly a chiral. (2007)
26. CH, CHCI- CH, -CH, has a chiral centre. Which
one of the following represents its R-configuration?

(a) H-Ç-CH, (b) Cl-C-CH,

CI H

ÇH3
(c) H-C-CI (4) H,C-Ç-CI
H (2007)
27. Which of the following is not chiral?
(a) 2-Hydroxypropanoic acid
(b) 2-Butanol
(c) 2,3-Dibromopentane
(d) 3-Bromopentane (2006)
28. Which of the following undergoes nucleophilic
substitution exclusively by SNl mechanism?
(a) Ethyl chloride
(b) Isopropyl chloride
(c) Chlorobenzene
(d) Benzyl chloride (2005)

29. The chirality of the compound

Br

C*||H is

H,C CI
(a) R (b) S
(c) E (d) Z (2005)
30. Which of the following is least reactive in a
nucleophilic substitution reaction?
(a) (CH),C - CI
(b) CH,=CHC1
(c) CH,CH,CI
(d) CH, =CHCH,CI (2004)
31. Which of the following pairs of compounds
enantiomers?

CH, CH¡
H OH HO -H
and
(a) HO H H OH

CH, CH3
CH, CH,
H OH HO H
and
(b) HO H HO H

CH, CH,
CH, CH,
H OH IH OH
and
(c) HO H IH OH

CH, CH,
CH, CH
HO H and HO.
HO H
(d) H OH HO H

CH, CH, (2003)

32. Reactivity order of halides for dehydrohalogenation
is
(a) R-F>R- Cl> R- Br> R-I
(b) R- I>R- Br > R- Cl> R- F
(c) R-I>R-Cl>R- Br >R-F
(d) R-F>R-I>R- Br >R- CI (2002)
33. CH,CH,CI
NaCN
’X Ni/H,
acetic anhydride
Y
Z in the above reaction sequence is
(a) CH,CH,CH,NHCOCH,
(b) CH,CH,CH,NH,
(c) CH,CH,CH,CONHCH,
(d) CH,CH,CH,CONHCOCH, (2002)

34. CH,-CH,-ÇH-CH, obtained by chlorination of

Cl
n-butane will be
(a) meso form (b) racemic mixture
(c) d-form (d) 1-form. (2001)
35. An organic compound A(C,H,CI) on reaction with
Na/diethyl ether gives a hydrocarbon which on
monochlorination gives only one chloro derivative
then, A is
(a) t-butyl chloride (b) s-butyl chloride
(c) iso-butyl chloride (d) n-butyl chloride.
(2001)
36. A compound of molecular formula C,H6 shows
optical isomerism, compound will be
(a) 2,3-dimethylpentane
(b) 2,2-dimethylbutane
(c) 2-methylhexane
(d) none of these. (2001)
37. Which of the following compounds is not chiral?
(a) CH,CHDCH,CI (b) CH,CH,CHDCI
(c) DCH,CH,CH,CI (d) CH,CHCICH,D
(1998)
 38. Replacement of CI of chlorobenzene to give
phenol requires drastic conditions. But chlorine
of 2,4-dinitrochlorobenzene is readily replaced
because
(a) NO, donates e at meta position
(b) NO, withdraws e from ortholpara positions
(c) NO, makes ring electron rich at ortho and para
(d) NO, withdrawse from meta position.
(1997)
39. The alkyl halide is converted into an alcohol by
(a) elimination
(b) dehydrohalogenation
(c) addition
(d) substitution. (1997)
40. The following reaction is described as
H,C(CH), OH
(ÇH),CH,
Cc- Br HO C
H,C H CH,
H
(a) SE2 (b) SyO
(c) S2 (d) Sl (1997)
41. Reaction of t-butylbromide with sodium methoxide
produces
(a) sodium t-butoxide
(b) t-butyl methyl ether
(c) isobutane
(d) isobutylene. (1994)
42. Grignard reagent is prepared by the reaction
between
(a) magnesium and alkane
(b) magnesium and aromatic hydrocarbon
(c) zinc and alkyl halide
(d) magnesium andalkyl halide. (1994)
43. Chlorobenzene reacts with Mg in dry ether to give a
compound (A) which further reacts with ethanol to
yield
(a) phenol (b) benzene
(c) ethyl benzene (d) phenyl ether. (1993)
44. Benzene reacts with n-propyl chloride in the
presence of anhydrous AlCl, to give
(a) 3-propyl-1-chlorobenzene
(b) n-propylbenzene
(c) no reaction
(d) isopropylbenzene. (1993)
45. Which chloro derivative of benzene among the
following would undergo hydrolysis most readily
with aqueous sodium hydroxide to furnish the
corresponding hydroxy derivative?
NO,
(a) O,N-C (6) O,N-Oa
NO,
(c) Me,N-<O-a () CçH,CI
cHCI (1989)
46. Which of the following is an optically active
compound?
(a) 1-Butanol (b) 1-Propanol
(c) 2-Chlorobutane (a) 4-Hydroxyheptane
(1989)

10.8) Polyhalogen Compounds

47. Trichloroacetaldehyde, CCl,CHO reacts with
chlorobenzene in presence of sulphuric acid and
produces
CI

OH
(b)
Cl

CCl,

CH,CI (2009)

Industrial preparation of chloroform employs

acetone and

(a) phosgene
(b) calcium hypochlorite
(c) chlorine gas
(1993)
(d) sodium chloride.
49. Phosgene is a common name for
(a) phosphoryl chloride
(b) thionyl chloride
(c) carbon dioxide and phosphine
(d) carbonyl chloride. (1988)

50 NaOH +? NEET
CH,CH,CO0»Na.
RKT Heat 2021

CH,CH, + Na ,CO,
Consider the above reaction and identify the
missing reagent/chemical.
(a) BH (b) Red phosphorus
(c) CaO p(d) DIBAL-H
51 The major product of the following chemical NEET
reaction is 2021
CH,. >CH -CH=CH,+HB.CH,CO),0,
?
CH

(a) CHs. CH-CHy CH Br

CHS
(b) CH3. CH- CH
CH3
CH,.>CH
(C) CH,
CH,
Br
CH,.
(d) CHCBr-CH CH
CH,
52 The major product formed in NEET
dehydrohalogenation reaction of 2-bromo 2021

pentane is pent-2-ene. This product

formation is based on
(a) Saytzeffs rule (b) Hund's rule
(c) Hoffmann rule (d) Huckel's rule
53 The incorrect statement regarding chirality NEET
is : 2022
(1) Syl reaction yields 1:1 mixture of both
enantiomers.

(2) The product obtained by Sy2 reaction

of haloalkane having chirality at the
reactive site shows inversion of
configuration.
(3) Enantiomers are superimposable
mirror images on each other.
(4) A racemic mixture shows zero optical
rotation.
54 The given compound 2023
CH = CH-CH-CH, CH,
X

isan example of
(1) aryl halide (2) allylic halide
(3) vinylic halide (4) benzylic halide