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21931 Roll No.


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No. of Pages
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Total No. of Questions : 09


B.Tech. (Petroleum Refinery Engg) (2013 Onwards) (Sem.3)
21931 21931 21931 ORGANIC
21931 21931CHEMISTRY
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Subject Code : BPTC-301


Paper ID : [A3259]
21931 Time : 3 Hrs.
21931 21931 21931 21931 21931 Max. Marks
21931 21931 : 60 21931

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
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attempt any 21931 21931
T WO questions. 21931 21931 21931 21931

21931 21931 21931 21931 SECTION-A


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1. Write briefly :

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a) Write the structure21931
of the product21931
A and explain21931
its formation21931
: 21931 21931

Pd/C, quinoline S
H2 + PhCH2CH2COCl A.
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b) Write the isomers of the compound having formula C4H9Br.

c) Write the product of each of the following reactions :


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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

d) What do you understand by reducing sugars? Give example.


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e) Compare the acidities of ClCH2CH2OH and CH3CH2OH with explanation.

f) Account for the following differences in acidity :


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(a) FCH2COOH > ClCH2COOH

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ClCH2COOH 21931
> ClCH2CH2COOH.
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21931 1|M
21931 code-72190
21931 21931 21931 21931 21931 (S2)-2785
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g) Account for the following order of increasing basicity:


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RC N < RCH = NR < RNH2.

h) Define the term epimer and illustrate with threose and erythreose.
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i) Write the structure of Malachite Green.

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j) Define
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aromaticity21931
with example.21931 21931 21931 21931 21931

21931 21931 21931 21931 SECTION-B


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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.

4. Account for the following order of decreasing basicities :


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(a) pCH3OC6H4NH2(E)>C6H5NH2(A) >oCH3OC6H4NH2(F)>mCH3OC6H4NH2 (G)

(b) pCH3C6H4NH2(H)>mCH3C6H4NH2(I) > C6H5NH2(A)> oCH3C6H4NH2 (J)


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5. Write short note on Hell-volhard-Zelinsky reaction and Give their mechanism.

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

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SECTION-C
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7. (a) Describe the Lucas test for distinguishing between 1, 2 and 3 alcohols.

21931 21931 (b) Write a short note21931


21931 on Aldol Condensation.
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(c) Account for the following order of complex formation with BMe3 :
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Me2NH > MeNH2 > NH3 > Me3N.

(d) Explain why the CO bond in phenol is shorter than in alcohol.


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(e) Account for the formation of osazone from a 2-ketohexose.

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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)
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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
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(i) Write all the possible structures for X

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(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
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following pairs21931
: 21931 21931 21931 21931 21931

(i) PhCH = CHCH2OH and PhCH = CHCHO


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(ii) 21931
PhCH2COCH221931 21931
CH3 and PhCH(OH)CH 21931
2CH2CH3
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(c) Complete the following :


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(i) PhCOCH2CH3 + SO2Cl2

(ii)
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21931 3|M
21931 code-72190
21931 21931 21931 21931 21931 (S2)-2785
21931 21931

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