NATIONAL INSTITUTE OF TECHNOLOGY ROURKELA

END-SEMESTER EXAMINATION, 2018

SESSION: 2018-19 (Autumn Semester)

Subject code: CY-2101 Subject Name: Hydrocarbons and Their Functional groups Dept. Code: CY
No. of pages: 2 Full Marks: 50 Duration: 3 h
Date: 22.11.2018 Time: 8.30 am

Answer all questions

Figures in the right hand margin indicate marks
Q.
No. All parts of a question should be answered at one place Marks

1 Write three methods of preparations with mechanistic details for the following 4x3
compounds. each

2 Explain how a mixture of 1°, 2° and 3° amines can be separated by Hinsberg’s 3

method.

3 Write the possible product(s) with mechanistic details [0.5+1.5] for the following 4x2
reactions. each

4 Write short notes (Importance, reaction pathway) on the following with suitable 4x3
examples. each
a) Iodoform reaction
b) Nucleophillic Substitution reaction with alkyl halides
c) Hoffmann-Martius rearrangement
d) Diazonium compound (one synthetic method and One use)

5 Describe the relative reactivity of acid derivatives (ester, acid chloride, acid 2
anhydride and amide) towards nucleophilic addition considering H2O as the
nucleophile.

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6 Answer the followings with suitable reasoning. 5x2
a) Which among ethanol and ethanthiol is more acidic? each
b) Which among n-butanol and phenol is more acidic?
c) Explain the boiling point differences of CH3NH2 (b.pt. 6.5 °C), CH3OH (65 °C),
CH3COOH (118 °C).
d) Arrange 1°, 2° and 3° amines in the ascending order of their boiling points.
e) Write and explain the difference in the products for the addition of MeMgBr
(Grignard Reagent) and Me2CuLi (Gillman reagent) with vinyl methyl ketone.

7 Write one chemical reaction showing the reaction pathway for the following 3x1
compounds. each

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