bnemiStry

DPP 5.2
Nucleophilic Addition Reactions
Ltd.
Single Correct Answer Type
1. Which of the following compounds has the largest (a) OH

equilibrium constant for the addition of water?t

QH
(a) CH,0
(C) (d) Allof these
(b) -NO,

(c)
YaX 1av 5. Acompound X(C,H0,) upon treatment with CH,MgX
gives 4 moles of methane. Identify the structure of (X)
OH QH OHe sfaute
(d) -NO,
(a) ( (6) CHO
ta) 0 OH ÖH OH
2. CHH D,os (c)
OH O
yOH (b(d) .5
OHliblold
DCHH OH OH -OHs) A
180 arnin
The intermediate is Br
CH,MgBr
18OD 18 OD >(A)
1(eq.)
(a) CH,-¢-D (b) CH,-c-H CH=0
16OD 18OD (a) (b)
16OD H,
(c) CH;--H (a) CH,--H
16OD 16OD (c) (d)
CH,
CH,-OH CHO
[X] CH¡O. H
CH-Ph (i) KCN
CH,0 H 7. H -OH ’ Products
3. (u) HO
H OH H -O
H CH,OH
H -0CH3 -0CH3
Products obtained in the reaction is
CH,OH CH,-OH (a) Racemic mixture (b) Diastereomer
Compound (X) in the above reaction is (c) Meso compound (d) Optically pure enantiomer
8. The correct statement/s about the following reaction
(a) Ph-C-H) (b) Ph -C- CH, sequence is/are
Cl,/FeCls HNO, + H,SO4 HNO, + H,SO4, A NH,NH, A

(c) Ph-CH, -C-H (d) Ph-CH,-C-CH,

(1) (2) )
O,N. P>(P)(4)
-CH=N-NH -NO,-(0)
(5)

(a) R'gives an alcohol condensation reaction on heating

with NaOH solution
1mole CH; Mg X
4. +H,0 P). The product (P) is (b) Step (4) is an aromatic nucleophilic substitution
reaction
(c) The compound 'Q' gives ayellow precipitate in acetone
(d) The end product is a mixture of three compounds
 Aliphatic and Aromatic AldYhydes and Ketones 5.5
9. The following preparation of caprolactum from the oxinme 14. Analyse the following reaction. If
of cyclohexanone involves a rearrangement called
NH
HOCH,CH,COCH,CH,CO,Et
(NOH ICH,MgX -’P
ICHMgX0 1CH;MgX ’R

(a) Pinacol-Pinacolone rearrangementoaall d (a) EIO - C-CH,-CH,-C-CH,- CH,OMgX

(b) Claisen rearrangement
(c) Beckmann rearrangement
CH,
(d) Curtius rearrangement
10. Which of the following will be the product of the following
reaction?
(b) EtO -C -CH, - CH, - c-CH,CH,OMEX
ÔMgX
ÇHS
(0+HO-CH,-¢-CH-0H acid
(c) CH,-C -CH,- CH, C-CH, - CH, -OMgX
CH,
HO-3 (excess)
bens un CH,
(a)
(d) CH,-c-CH,-CH,-C-CH,-CH, - OMgX
(c) (d)
OMgX
Which is/are correct?
11. An organic compound C,H,0 does not give a precipitate (a) Pis (a) (b) Q is (a)
with 2, 4-dinitrophenyl hydrazine reagent and also does (c) R is not (d) (d) Q is (b)
not react with metallic sodium. It could be
(a) CH,CH,- CHO (b) CH,=CH -0CH, 15. Which of the following correctly indicate(s) the rate?
(c) CH, -COCH, (d) CH, =CH- CH, OH
(a) CH,CH
CN CH,CHO
(very fast) KCN +
HCI
Me
oCHO
(slow)
Multiple Correct Answers Type OH

12. In which of the following reactions deuterium exchange Me

is observed? CN
D,o-OH
(a) CHy G-CH-CH; exces CD; CCD CH; Ph Ph
CH,CH=0
D,o/OH (b) (hydrate) H,O/H* ’ hydrate
(b) CHrÇH-Ç-H CH, CD-c-H (fast)n o (slow)t.
H N/OH9 CHMgBr
(c) Cyanohydrin slow C,H,CHO fast

D Adduct formation
D,oÔH
(c) D) (d) Allof these

(d) H-C-H- D,0/OH ’D-C-D 16. Observe the following reaction:

HCN (excess)
CH, -C-CH,-C-CH,
Products.
13. In which of the following reactions deuterium exchange
is not observed?
The correct statement is
Ph. CH, (a) The product is a mixture of two conmpounds
(a) CH,
(b)
Ph (b) The product is optically inactive
(c) The product is a mixture of two chiral and one achiral
Me stereoisomer
LCHO
(c) (d) Ph
H,C
Br (d) The product is a mixture of three stereoisomers
 Linked Comprehension IypE
Matching Column Type
For questions 2-22
17. Mach e vnoitose in oohn l NHOH so
Akkebydes nd keSreact i
ese ca
keorimes respeively. Corfgraion of
Cokumni Colsmnl
Reactions) Products)

2WLOH
Formaion of
p.six enbere
ring tkes place
OH

Finel product
OH
3-nsatred
kesone
20. (X] #,BPa-NH,+ CH,-C-OH
Final protuct
c #C-C-CH-CH,-CH,--# formed will
Identify the onfizrztion of [X] compound
give positive
Tolen's test (a)
CH
Ps
CH, Fnal product
formed will
react with 2.
CHoH
Ph
4-DNP
CH-CHN
Ping expansion P
takes place () CH-CH
NumericalValue Type 21. Whích step is a rate determining step?
(2) II (b) III (c) IV
18. Aronatic catonyi conpOs having molecukar frmula
CHO react wih NHOH. H¡w mar oxines can be
Eormed? 22.
(Z)eyeskynas B).
19. Exzrise tte srsctural foTuls of folSowing conpounds
ad fird t ube of coos hích show hígher The product (B) ís
rae of ruclephilc aitin rein than (a) NH,-CH-COOH
CH,
CH,-COOH
(b)
H,- NH,
NH,
(c)
C, -OH
(d)
 ANSWER KEY

Single Correct Answer Type Matching Column Type

1. (b) 2. (d) 3. (a) 4. (c) 5. (d) 17. (a ’p, 4, s, t), (b ’ p, t), (c -’p, q, s), (d ’p, q, S, t)
6. (b) 7. (b) 8. (b) 9. (c) 10. (d) Numerical Value TypeoWesh a o
11. (b) HO
18. (10)19. (3) otbo
Multiple Correct Answers Type l iPav t .
Linked Comprehension Type
12. (a, b, c) 13. (a, c) 14. (a, c, d)
15. (a, c) 16. (b, d
c, )fo 20. (b) 21. (a) 22. (b)

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