Tpoic 11

Types of Reaction Mechanism

O14
Which one Is ost reactive towards nucleoplhilic addition 7. Which of the following applies in the reaction? (AIIMS]
1. (CBSE AIPMTI Ale. ROH

-CHO
CH,CHBrCH,CH, ?

(b) -COCH; I. CH,CH-CHCH,major product +

(a)
II. CH,=CHCH,CH,minor product
CHO CHÌ
(a) Hofmann's rule
(b) Saytze ff's
(d) (c) Kharasch effect
(d) Markownikoffs rule
8. Under identical conditioins, Sy Ireaction will occur most
CH; NO, efficient with [WB JEE]
. n incomect statement with respect to Syl and Sy 2 (a) tert-butyl chloride
mechanisms for alkyl halide is [KCET] (b) 1-chlorobutane
(a) Astrong nucleophile in an aprotic solvent increases (c) 2-methyl-1-chloropropane
the rate or favours Sy2reaction (d) 2-chlorobutane
(b) Competing reaction for an SE2 reaction 9. The following reaction,
rearrangement H CH,
(c) Sy Ireaction can be catalysed by some Lewis acids Alcoholic
(d) Aweak nucleophile and a protic solvent increases the
rate or favours S lreaction CH,CH
CH, X
KOH, -H, 0,-KBr
3. The boiling points of four saturated hydrocarbons are
given below which boiling point suggests maximum CH,
number of carbon atoms in its molecule? [AIIMS]
(a) -162° C (b)-88.6° C (c) -0.5° C (d) -42.2°C
CH,Çc CH,
2012 CH;
4. Among the following compounds the one that is most is an example of LAMUI
reactive toward electrophlic nitration [CBSE AIPMT] (a) a-elimination
(a) benzoic acid (b)nitrobenzene (b) ß-elimination
(c) toluene (d) benzene (c) Hofmann elimination
S. Consider the reaction, (d) None of the above
RCHO +NH,NH, ’ RCH =NNH,. 10. Which one of the following undergoes S2 reaction
What type of reaction is it? [CBSE AIPMT] faster [AMUJ
(a) Electrophilic addition elimination reaction
(b) Free radical addition elimination
reaction -CH-CI
9 Electrophilic substitution elimination
(0) Nucleophilic addition reaction CH, CH,
6. Which of climination reaction.
the following does not show Sy2reaction?
(a) Vinylic halide > C= -CH,CI
(b) Allyl chloride CHX [AIIMS)

(c) Chlorobenzene
(d) All of the CH=CH,Cl
above
 244 | Chapterwise &
Topicwise Medical Entrances Solved Papers

Ion11. Which of the

following
electrophilic reagent?
is the most reactive towards
(CBSE AIPMTI
CH;

(a) CH, -CH, (b) CH, Br

(b) CH,
CH,OH OCH,
CH,
(c) .CH: (d)
CH;
(c) H -Br
OH NHCOCH,
12. Which one is a C,H,
nuclecophilic
the following? substitution reaction among H
[CBSE AIPMT]
(a) CH,CHO + HCN ’ (d) H--CH,-CH,-CH,
CH, CH(OH)CN
() CH,-CH -CH, +H,0-H, Br

CH,-CH-CH, 16. Which of the following is nucleophilic addition reac

(a) Hydrolysis of ethyl chloride by NaOH
(c) RCHO +R'
OH
(b) Purification of acetaldehyde by NaHSO, [Guj CE
MgB’ R-CH-R (c) Alkylation of anisol
OH (d) Decarboxylation of acetic acid
CH, 2010
(d) CH,-CH,-CH -CH,Br +NH, 17. The correct order of increasing reactivity of CXbond
towards nucleophile in the following compound is
X
[CBSE AIPT
X

13. The
CH,-CH,-CH- CH, NH, NO,
compound that does not undergo hydrolysis by SN 1
mechanism is
(Kerala CEE]
. (CH;)3C-X (CH),CH-I
(a) CH,=CHCH,Ci
(b)CçH,Cl NO,
(c) CçH, CH,CI (I) (I) (I)
(d) CçH_ CH(CH, )CI (IV)
(e) CgH, CH(C,H, )Ci (a) III <II<I<IV (b)I<II<IV<II
14. Which one of the following alkylbromides undergoes most (c) II<III<I<IV (d) IV< III <|<II
18. Ethanolic KOH gives
rapid solvolysis in methanol solution to give corresponding MHT CET
methyl ether? [DUMET] (a) dehalogenation reactions
(b) dehydrogenation reactions
(b) Br (c) dehydrohalogenation reactions
(d) substitution reactions
19. The SNl reactivity of the following halides will be
order
(c) Br (d) [Manipal
I. (CH;), CBr
III. (CH,),C(CH,)Br II. (CH,), CHBr
Br IV. (CH),CHBr
V. C,H,Br
15. Which will undergo fastest Sy 2substitution reaction when Codes
teated with NaOH? (a) II> I>
(c) V> III>V> IV
[DUMET]
(b) I> II>V>[>IV
CH, 20. SN I>II>IV> III (d) II >II>I>V>V
Br
lreaction of alkyl
(a) retention of halides leads to Manipall
(a) H,C; (b) racemisationconfiguration
H (c) inversion of
(d) None of the configuration
above
 ues Z40
1.Inthe following halogen compounds, which
undergoes fastest SNlreaction? compound 29. Find the major product
Cl [RPMT] (considering
when the following substrate Eas the
is subjected to electrophile)
II.
aromatic substitution. electrophilie
(0JEE)

(a)1 (b) I
(c)lll (d)None of these
Which of the:following compound is most reactive (a)
nucleophilic addition reaction2 towards
[RPMT]
(a) Ethanal (b)Propanal
(c) Butanone (d) Propanone (b)
1. Presence of anitro group in a benzene ring [RPMT] E
(a) renders the ring basi
b) deactivates the ring towards nucleophilic substitution
ic) deactivates the ring towards electrophilic substitution (c)
(d) activates the ring towards electrophilic substitution
4. The following reaction is described as [CMC]

OH’ HO cH), CH,

CH; (CH, )s (d)
C- Br
H,C
H
|CH,
H 30. Correct order of reactivity towards electrophilic
(a) S 2 (b) S, 2 (c) SE 1 (d) Sy 0 substitution on the following substrate is [OJEE]
25. Which kind of fission is favoured by sunlight? [VMIMC] CI CH, NO,
(a) Heterolytic fission (b) Homolytic fission
(c) Both a' and b' (d) None of the above I. I. II. IV.
26. Assertion (A) In SE Ireaction on 2-bromobutane, product (a) I> IV>H> II (b) II >I>I|>V
formed is a racemic mixture.
(c) II> IV>I>II (d) I> II> II> V
Reason (R) Carbocation is the intermediate of S
reaction. [VMMO] 31. Order of reactivity towards nucleophiic substitution
reaction of the compounds [AMUJ
(a) Both A and R are correct and R is the correct
explanation of A NMe, NO, CI
(b) Both A and R are correct but R is not the correct NO, 0,N NO,
explanation of A
(c) A is correct but R is incorrect
(d) BothA and Rare incorrect
Cl CI NO, NO,
009 I. II. III. 1V.
21. Which of the following reactions is an example of (a) I> II>II>IV (b) II >1>II>IV
nucleophilic substitution reaction? [CBSE AIPMT] (c) IV>III>II>I (d) IIl> V >II>I
(a) RX + KOH ’ ROH+ KX
(b) 2RX +2Na R-R+ 2NaX 2008
towards
(c) RX + H, ’ RH+ HX 32. Which one of the following is the most reactive
(d) RX + Mg ’ RMgX electrophilic attack? [CBSE AIPMT]
28. The product of which of the following reactions has the
-CH,OH NO
highest ease to undergo clectrophilic substitution? [AIIMS] (a)
(a) C,H,COCI Pd/ BaSO4 C1
(b) CH, Cl,/FeClg -OH
CHCI/ Anhy. AlCly
(c)CH,
(d) C,H,0H Conc. H,SO4
 33. In a SN 2substitution reaction of the type
DMF
40. Most reactive compound towards selectrophilic subsi
R - Br+ C1 ’ R-Cl+ Br

Which one of the following has the highest relative rate?

[DUM
[CBSE AIPMT] OC,Hs CH,
(a) CH;CH, -CH,Br (b) CH,-CH-CH, Br (b)
(a)
CH,
C1

(c) CH,C-CH, Br (c) (d) None of these

(d) CH,CH, Br
CH,
41. The formation of cyanohydrin from acetone is
34. The hydrolysis of 2-bromo-3-methylbutane by S l of reaction? which tr
[Guj CE
mechanism gives mainly [Kerala CEEJ (a) Electrophilic substitution reaction
(a) 3-methyl-2-butanol (b) Electrophilic addition reaction
(b) 2-methyl-2-butanol (c) Nucleophilic addition reaction
(c) 2,2-dimethyl-1-propanol (d) Nucleophilic substitution reaction
(d) 2-methyl-1-butanol
(e) l-pentanol 2007
35. The reaction, 42. The order of decreasing reactivity towards an electroni
CH,=CHCH, + HBr ’ CH,CHBrCH, is reagent, for the following [CBSE AIPME
type of [Haryana PMT] I. Benzene II. Toluene
(a) electrophilic addition reaction. III. Chlorobenzene and IV. Phenol
(b) nucleophilic addition reaction (a) I> II> II > I
(c) free radical addition reaction (b) II>IV> [>II
(c) IV >III> I[> (d) IV >II>.>II
(d) electrophilic substitution reaction
43. Williamson's synthesis involves [MHT CET
36. Dehydration of alcohol is an example of which type- of
reaction? [J&K CET] (a) SE Imechanism (b) nucleophilicaddition
(a) Substitution (c) Sy 2 mechanism (d) S mechanism
(b) Elimination
(c) Addition (d) Rearrangement 44. Which of the following is least reactive in
substitution reaction? nucleophil
37. Conversion of chlorobenzene to phenol involves [Manipa
(a) electrophilic substitution (a) (CH, )C-CI (b) CH, CHCI
[J&KCET] (c) CH,CH, CI
(b) nucleophilic substitution (d) CH, CHCH,CI
(c) free radical substitution
(d) electrophilic addition 2006
38. t-butyl chloride preferably undergo hydrolysis by 45. Assertion (A) The presence of nitO group
(a) Sl mechanism [Punjab PMET] nucleophilicsubstitution reactions in aryl halides.facila
(b)SE2 mechanism Reason (R) The intermediate
of nitro group. carbanion stabiliseu
(c) Any of 'a' and 'b to the is
(d)None of the above presence
(a) Both A and R
[AIMS

39. Reimer-Tiemann reaction involves a are correct and R is the corte

[AMU] explanation
(b) Both A and R
of A
(a) carbonium ion intermediate are coIrect but R the coned
(b) carbene intermediate explanation of R is not
(c) carbanion intermediate (c) A is correct but
(d) free radical intermediate (d) Both A and R R is incorrect
are
incorrect