INSTRUCTIONS TO CANDIDATES :
1. SECTION-A is COMPULSORY consisting of TEN questions carrying T WO marks
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each. 21931 21931 21931 21931 21931 21931 21931
2. SECTION-B contains FIVE questions carrying FIVE marks each and students
have to attempt any FOUR questions.
3. SECTION-C contains T HREE questions carrying T EN marks each and students
21931 21931 have to21931
attempt any 21931 21931
T WO questions. 21931 21931 21931 21931
1. Write briefly :
Pd/C, quinoline S
H2 + PhCH2CH2COCl A.
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HCN, ZnCl2
(a) Resorcinol A
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(b) 21931 21931
Me2NC6H5 + HCONMe 21931
POCl
2
3
B. 21931 21931 21931 21931
21931 1|M
21931 code-72190
21931 21931 21931 21931 21931 (S2)-2785
21931 21931
h) Define the term epimer and illustrate with threose and erythreose.
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j) Define
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aromaticity21931
with example.21931 21931 21931 21931 21931
2. a) Give the product of oxidation of KMnO4 of 1, 2 and 3 alcohols in acidic and basic
media.
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b) Why is KMnO4 not the reagent of choice for the preparation of methyl vinyl ketone
from the corresponding alcohol?
21931 21931 c) Why can MnO2 be21931
21931 used for this synthesis?
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3. Give the product of oxidation of each of the following alcohols with Cr2 O 72 in H2SO4.
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(a) (CH3)2CHOH
(b) (CH3)2CHCH2OH
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(c) Ph2CHOH
(d) Ph2C(CH3)OH
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(e) cyclopentanone.
6. (a) Give the product from the reaction of D-threose with PhNHNH2, show the
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intermediates and21931 21931
classify the product. 21931 21931 21931 21931
(b) Give the product from the same reaction with D-erythrose and account for the result.
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(c) What conclusion can be drawn about this reaction with epimers?
21931 2|M
21931 code-72190
21931 21931 21931 21931 21931 (S2)-2785
21931 21931
SECTION-C
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7. (a) Describe the Lucas test for distinguishing between 1, 2 and 3 alcohols.
(c) Account for the following order of complex formation with BMe3 :
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Me2NH > MeNH2 > NH3 > Me3N.
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8.
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(a) Write a mechanism
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for the oxidation
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of a 2 alcohol
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with Cr(VI)
21931
as HCrO4 .21931 21931
(b) Compare the ease of oxidation of cis- and trans-4-t-butyl cyclohexanol with a Cr(VI)
reagent.
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9. (a) Compound X, C9H10O, is inert to Br2 in CC14. Vigorous oxidation with hot alkaline
permanganate yields benzoic acid. X gives a precipitate with semicarbazide
21931 21931 hydrochloride
21931 and21931
with 2,4-dinitrophenylhydrazine
21931 21931 (DNPH). 21931 21931 21931
21931 21931
(ii) 21931
How can these21931 21931
isomers be distinguished by21931 21931
using simple chemical tests?21931 21931
(b) Give a simple chemical test to distinguish between the compounds in each of
21931 21931 the21931
following pairs21931
: 21931 21931 21931 21931 21931
(ii)
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21931 3|M
21931 code-72190
21931 21931 21931 21931 21931 (S2)-2785
21931 21931