EXER CISE -I

Q.l Rate ofhydration of

CH3
~CH -CH20 [:>---c Ha:CH CH t>:~H a:CH2
30
(I) (II) (ill)
will be in order:
(A) I < II < III (B) I < III < Il (C) II < I < III (D) III < II < I

Q.2 3-methyl-3-hexanol Cfill not be prepared by

(A) CH3MgI and 3-hexanone, followed by hydrolysis
(B) C2IfsMgl and 2-pentanone, followed by hydrolysis
(C) C3H_µgI and 2-butananone, followed by hydrolysis
(D) Ci19MgI and propanone, followed by hydrolysis

·-\1/hich of the following reaction is called as 'Bouveault-Blanc reduction'

(A) Reduction of acyl halide with HiPdBaSO
4
(B) Reduction of ester ,,vith Na/Ci~ OH
(C) Reduction of anhydride \\tith LiAlH
4
(D) Reduction of carbonyl compounds with Na/HgHCl

Q.4 B
NaBH 4
OcH =CH -CH O tt,/N, ,A
AandB are:

.· ' (A) 0 CH2CH2CHO, OC H= CH-CH,OH

. (B) 0 CH2CH,C HpH, 0 CH=C H-CH20H

(C) 0 CH=C H-CH ,OHin bothca ses

(D) 0 CH2CH2CH20H in both cases

Q.5
0-CHi . cold >A
alkalrneKMnO 4
Cr03
AcOH
>B

A and Bare:

- CtCH CtCH3 3 CH3 CH3

(A)
OH
OH'
OH
0 (B)
Ct
OH
OH'
0 0
0

/C) r/~A rYCH 3

(D) no formation of A and B
\ ~OH'~OH
Q ·6 How would you get racemic mixture of 1,2-butane diol from cis 2-butene.
OH
I .
CH3CH = CHCH (i)A > CH 3 -CH-CH -CH 3 ,A& Bare
3 (ii)B
I
OH
(A) A= KMnO/O H-, B = H20 (B)A= CF 3C0 3H, B == H 20
(C) A= OsO /OH-, B = H20 (D) A= O/H2 0, B = Ph3P

· OCH2C H3 OCH=C H2
· OH - ~ -

~
Q.7

Ob:CH, ocH,CH,OH
- - - -

Select schemes A, B, C out of

I acid catalysed hydration II HBO III oxymercuration-demercuration
(A) I in all cases (B) I, II, III (C) II, III, I (D)III, I, II

Q.8
_f)H 9H _
~ . In this diol
(A) 0 Hat C2 is more basic than that of at C5 (B) OH at C2 is more acidicthan at C 5 •
(C) both have same basicity (D) both have same acidic strength

Q.9 · H+ . ? Product is:

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

Q.10 Dehydration ofthe alcohols

;\_OH

(I)
~
(II)
OH >i (III)
~OH

(IV) ·

wiHbe in order
(A) IV > III > II > I (B) I > II > III > IV (C) IV> II > III> I (D) II > IV > I > III
 . .
Q .11 Which one [Link]-wm g can not be the produ-ct dunn
. .
g dehydration offiO1lov.ino0 alcohol.

(C)o (D
)o
XH -NH 2 2

Q.12 V NaNO 2
HCI
A

Ais

(A) 0 -. (B)o
OH CH')-OH OH CHrC I

.(D)o A

Q.13 CH3MgB r+ Q 0
A
HBr
B Mg / ether ) C HCHO )
Ho+
3
D ID) E

Eis

(C) r'l
- Yi CH3

I2 / NaOH
Q.14 Li A, A is
Li

.(A)o 0
. 60~ C-OH
-

O
.-
0
II
C-OH
~' 0

(B) (C) (D)

0 OCH 3

Q .15 Ethanol on reaction with acetic anhydride gives

(A)Acetic ester (B) F0Im1c ester
(C) Ethanoic acid (D) Acetic ester and Ethanoic acid both

Q .16 Glycol on heating with PI mainly gives-

3
(A) Ethylene (B) Ethylene iodide (C) Ethyl iodide (D) Ethane
 KHS04 ) A LiAIH4 >B
Q.17 Glycerol fj.

A and Bare:
(B) Glyceryl sulphate, acrylic acid
(A)Acrolein, allyl alcohol
(D) Only acrolein (B is not formed)
(C)Allyl alcohol, acrolein
~

Q.18 Hy:_ ~ CI Ale. KOH > Majorproductis

0

(A) H"'o ~ o"'H (B) H" 'o~

(C) H" 'o~ (0) 00

Q.19 Phenol withHinsberg's reagent gives

(A) Sulphone · (B) Sulphanilic acid ,Jr}-Sulphonic ester (D) Sulphonal

_@(O H (i)CHC! 3 +KOH

Q.20 _ [X] here 'X' is:
OH ~ii)CH2I 2,6

. @
(A) 0
· OH (B) ~OH .

HOOC . OH . OH C~O H

(C) @ o'----
. CH2
(D) rryocH 3

OHC o/ · OHC ~OC H3

Q.21 CH 2 = CHCHCH 2 CH 2 0H Mno 2 > [Link] s

~
I
OH
(B) CH 2 = CHCHCH 2CHO
I
OH .

0
II
(C) CH 2 = CHCCH 2 CHO (D) CH 2 = CHCCH 2COH
II II
0 ·o

(D)None
 CH 3
Q.23 CH 3 -~- t-C H
3
~ Me 3C-I + Me-O H true about this is
I I
H CH 3
(A) Me3C-0M e with anhydrous HI gives this reaction
(B) Me3C-0M e with concentrated Hi gives this reaction
(C) both of the abov e
(D)n one

· 9 .2 4 The reaction of CH OC H with HI gives

3 2 5
(A) CH31 (B) C2H 0H
5

Q.25 Consider the reaction ofHI with the following:

I
0
Whic h forms di-iodide on reaction with HI (excess)?
II
00
(A) I and II both (B) II only (C) I only (D)n one

0
Q.26 . I\ ~R'
RMgX
H 0 . ➔
2
? Product Obtained is:
~R"

R R' R R
I I I I
(A) R'-C -CH 2 0H (B) RCH 2 -C-O H (C) R'CH -C-O H (D) R"C H -C- OH
2 2
I I I I
R" R" .R'' R'

· 1s e
Q.27 NO - CH - CH2 OH /MeOH > 'A'
2 "a /
Product 'A' is:

18
OH OH
I I
(A) N0 2 - CH - CH2 (B) N0 2 - CH ---?H 2
I .
OH . OH
18

18
OH OH
I I
(C) N0 2 -CH -CH 2 (D) N0 2 - CH - CH 2
I I
OH OH
18
Q.28 ~
.:-
~ H 30 e A. 'A'is

CH3
OH

(A)A
\__/-cH 3
(D)6-CH,
OH OH

Q.29 (A) (B)A&Bare:

(A)
0H~ H- 3
&.
.~H OH 3

H3CO OH OH CH 3

(C)
rr
H . . . ·oH
3
&,
'.

·,
u.·' .
MeO
.
·o.·

CH3
. (D)

9H3 Hz018 ) A .
Q.30 B CH 3-C-CH2
. · CH 3ONa
'd H+

AandB are

CH 3 CH 3 CH 3 · CH
I I I I 3
(A) CH 3 -C-CH 2 , CH 3 -C-CH 2 (B) CH 3 -:-C-CH 2 , CH -C-CH
I I I I I I 3 I I 2
18
0H OH OH OCH 3 OH 180H OH OCH
. 3

CH 3 CH 3 CH3 CH
3
I I I .. I
(C) CH 3 -C-CH 2 , CH 3 -C-CH2 (D) CH3-C-CH2' CH3 -:C-CH2
· I I .I I I I · I I
isOH OH OH 180H 18
· 18 180H 0H · OCH 3 OH
 Q .3 1 In the- following reaction, final product is
14
NaOC,H~
CICH., CH - CH 1
- \0 / -

14
14
(A) ClCH 1 CH C H 2 0 C 2 H 5 (B) CICH 2 CH C H 2 0Na
I I
OH OC 2H 5

14
14
(C) C H 1 - CHCH 2 0C 2 H 5 (D) CH 7 - CH C H 2 0C 2 H 5
\ 0 I \0 I
Question N o 32 to 34 (3 questions)
500°C No reaction

LiA IH4 B

NaBH 4 ~
' - - -~ ~CO OH

Q.3 2 Compo un_d ~B' is?

( A ) a .· ... (B) Q-- coOH (C)@ -CH,- --OH . (D) ~CH 3

Q .3 3 Organi c compo und A does not undergo de carboxylation reaction because ?

(A) Interme diate does not follow Saytzefl'n rule
(B) Interme diate does not follow Hofinann's rule ·
(C) Interme diate does not follow Bredt's rule
(D) Interme diate does not follow MarkwoniKoffs rule

Q.3 4 Total No. ofstere oisome rs ofB are?

(A}2 _ . (B)4 _ - (C) 3 (D)6

-- - - . -a•·
Q.35 Oxali cacid +A--- ~ : ( )
. 0

-> B, B is:
hence A _c_on_c._H_2s_o4~
0 . . 0 0
(A)() (B) o=c) _
(C) CH 2 -O-C H 2
I I
(D)o=( }.o
0 0 0
OH · OH
 EXERCISE-II

Q.1

(A) ~ -
(C)o (D)o
HBO, o>..ymercuration-demercurationand acid catalysed hydration \:[Link] not give same product in

C , true about the product C is

Q.2 In the reaction sequence, CaC 2

(KJ Give yellow ppt. [Link] NaOI

(B) It's final oxidation product is carbonyl compound
. _({}'_, Its final oxidation product is CO 2 and H 2O
(D) Its final oxidation product is CH.,COOH
_,

Q .3 Compound which gives alcohol on reduction is/are 0 0

II \\
(A) :tv1e-C-Cl (B) Me-C-NH 2 (C) Me-CH-CH 2 (D) Me-C-0-C- M e
. 'I
II II \ 0 I
·o 0
Q.4 Identi:f.)1 Band C (respectively) in following conversion.

0 conc.:2S04 )

OH
A Os04 )
H30EB
B
.
9
H
t.
C

(A)CY-D
OH
& 0--0
OHOH
(B) &
0--0
ccil/D
OH
(D) None of these
OH
&
Cb
Q. 5

(A)
Clu
Select the correct synthesis products

I BH3 ·THF H 20 2 ,0lr NaOH

0
CB)
Clu I
Hg(OAc)i
H 20
)
NaBH 4 NaOH

a
 xaOHJ H 2 0 >Product is:
Q.6 j 9s=c

(A) @f°H
(B)@LH
CI H O ~ CI
(C)
HO
J§f (D) 0
Q. 7 Methanol can be distinguished from ethanol by ·
(A) Heating with½ and alkali · (B) Treating with schiff's reagent
(C) Treating with Cr0 3 solution in dil. H2 SO4 (D) Treating with Lucas reagent

. Q.8 Lucas test is used to make distinction between 1°, 2° and 3° alcohols
ROH + HCl anhydrous ZnCl 7
cone.
White turbidity
This shm,vs that
(A) ROH behaves as a base .
(B) greater the value ofpKa (alcohol), greaterthereactivitywithconc. HCI and thus sooner the [Link]
ofwhite turbidity.
(C) alcohol which reacts fastest with Na metal, will give turbidity at fastest rate
(D) alcohol which gives red colour d ~ Victor Mayor test, will always give turbidity _at slower rate then
those giving [Link] white colour during Victor Mayor test ·

Q.9 End-product ofwhich offollowing reaction give positive Iodoform test.

0 0
II II
(B) Ph-C-O- Et (i) CH3MgBr (excess)
(A) H-C-Cl (i) CH3MgBr(excess)
(ii ) W (ii)Hs

0 0
II (i) CH 3MgBr (excess )
II (i) CH 3MgBr ( excess )
(C) H-C-O-E t (D) CH 3 -C-H
(ii ) H 9 (ii)HEB

Q.1 0 Dehydration of alcohols take place more rapidly with l P ~han with H 2 SO 4 . Select the correct
statement(s) about the following dehydration reaction. ~

aOH :;~ 0 v.

~«Cl4;'i u_7e+ •
(A) It does not involve carbocation.
(B) It 0 volves R---OPOCli with-OPOC 12 as a better leaving group. ·
(_C) It mvo~ves E2 mec~sm as pyridine base abstracts proton from the adjacent carbon as the same
tune at which- OPOC1i 1s leaving.
(D) It is El reaction without formation of carbocation.
 Q .11 Consider the following conipoundA(below)
OnOH
0
J-l OH 0
Select the correct statement(s) · .- ·a· th II
(A) It is more-acidic than CH3OH (B) It.1smore ac1 1c an CH,,COH .)

(C) It reacts very fast with Lucas reagent (D) Itis a diacidic base

HOY_
Q· 12 LJ HI > Products

ion?
Which of the following are possible products in the above react
I

(A) (B)o-A .I

Q .13 Products form by following reactions are

~ CHCli+KOH l

CH3
OH OH 0

(C)o
OH

(A}
~C HO
. (B) ~C HO
(D)
bCHO
CH3 CHCI 2 CH3
CH3 CH3
\

NaNO 2
Tilden
) (i) NH3 (ii) ➔ (iii). The product (iii) can be
Q.14 C2HsNH2 reagent HCI

(A)Alcohol (B)Ether (C) Alkyl chloride (D) Alkyl nitrite

Q.15 Which offollowing reaction represent major product.

0 0 OH

(A)
H3CD
0
II
NaBH 4 )
'Q HC
(B) ., D I
NaBH 4
➔ vH
II OH II
0 0 OH

OH 0 OH

H3CD 'QH
0

(C)
II
LiAIH~
)
'QH (D)D II

II
LiAIH, )

0
0 OH 0
 Q .16 Predict major organic prod~t from the following reaction: ·
0
H C II
3 T9 NaBH4:.:A
V \uAIH :.: B
~
4

0 OH

J\H 'C;JH
(A)~
II
0
~H

OH
(B)
~ OH OH

OH OH 0

(C)~
OH
~H

OH
(D) 't)H
0
~OH

Q .17 Which can [Link] by HIO4?

0 . 0 . OHO
· A 11 · II I II
( . ) CH 3CH 2 CCH 2 CCH 3 (B) CH 3CHCCH 2 CH 3

0
0 0
II II
~OH
(C) (D) CH 3CCH 2 CHCH 2 CCH 3
OH I
OH

Q .18 Which ofthe following will get oxidised by Br2 / KOH into carboxylic acid?

(A) CH --CH/0H
3
(B) [:>- I CH- <rn 3
OH
r-"\/OH
(C)OCHzO H (D) \.___pCH3

OH

Q.19 Q
CH3 . OH
Pee > (X) Major

OH 0 0 OH

(A)(lO (B)Q (C)O,

OH
(D)Q
0