NIR/KW/18/2080

Bachelor of Science (B.Sc.) Semester—III Examination

CHEMISTRY (ORGANIC CHEMISTRY) (NEW & OLD)
Compulsory Paper—II
Time : Three Hours] [Maximum Marks : 50
N.B. :— (1) All FIVE questions are compulsory and carry equal marks.
(2) Give diagrams and chemical reactions wherever necessary.
1.
6
(A) Define the term orientation. Discuss the directive influence of –NH2 group on further electrophilic
3
8
substitution on benzene ring.
(B) Discuss the mechanism of SN1 reaction with energy profile diagram. 5
5

OR

6
83
(C) Give Fittig reaction for formation of biphenyl. How will you prepare benzoic acid from
biphenyl ? 2½
(D) How are (i) Chloropicrin and
(ii) Phosgene, prepared from chloroform ? 2½
(E) How will you obtain toluene by Wurtz-Fittig reaction ? How is it converted to benzyl chloride ?
2½
(F) How DDT is prepared from chlorobenzene ? Give its uses. 2½
2.
3 6
(A) Give method of preparation of glycerol starting from propylene. What is the action of excess
of HI on it ? 8 5
(B) Discuss the reaction and Mechanism of Reimer-Tiemann reaction. 5
OR
(C) Discuss the mechanism of Pinacol-Pinacolone rearrangement reaction. 2½
(D) What is the action of following on ethylene glycol :
(i) dil. HNO3 and
(ii) Pb(CH3COO)4 OR HIO 4 ? 2½
(E) Discuss acidic nature of Phenol on the basis of resonance stabilization of Phenoxide ion.2½
(F) Write note on Gatterman Synthesis. 2½
3. (A) What is Aldol condensation ? Discuss its mechanism with example. 5
(B) Explain the structure of carbonyl group. How will you prepare the following :
(i) Acetophenone from benzonitrile and

3 6
(ii) Acetaldehyde from acetyl chloride ?
3 6 5
8 OR 8
(C) Discuss Wittig reaction with example. 2½
(D) Write a note on Cannizzaro’s reaction. 2½

BKR—11076 1 (Contd.)
 (E) What is the effect of following on Acetaldehyde ?
(i) Tollen’s Reagent and
(ii) Fehling solution ? 2½
(F) Give the general mechanism of nucleophilic addition to carbonyl group. 2½
4. (A) Discuss the acidity of carboxylic acids. What is the effect of electron withdrawing and electron
donating groups on the acidity of carboxylic acids ? 5
(B) What are esters ? What is the action of following on Ethylacetate :
(i)
3 6 Ammonia

8(ii) Thionyl Chloride

(iii) Hydrazine and
(iv) Hydroxyl amine ? 5

6
83
OR
(C) How is Cinnamic acid prepared from benzaldehyde in presence of :
(i) Sodium acetate and
(ii) Sodium ethoxide ? 2½
(D) Write a note on Hell-Volhard-Zelinsky reaction. 2½
(E) Discuss the mechanism of acid catalyzed hydrolysis of ester. 2½
(F) What is the action of heat on :

3 6
(i) Succinic acid and
(ii) Phthalic acid ?
8 2½
5. Attempt any TEN of the following :—
(i) Define O/P ratio. 1
(ii) Give uses of chloroform. 1
(iii) Which is more reactive : Chlorobenzene or benzyl chloride ? 1
(iv) What is the action of bromine water on phenol ? 1
(v) How is Trinitroglycerine obtained from glycerol ? 1
(vi) Give the structural formula of butane-2, 3-diol. 1
(vii) How acetone is obtained from methyl cyanide ? 1
(viii) What is the action of peracetic acid on acetone ? 1
O
||
(ix) Give the IUPAC name of CH3–C–CH2–CH3 . 1

6
(x) Give any two physical properties of carboxylic acid.
(xi) How is 3 36
1

8 phthalic acid obtained from o-xylene ?

(xii) How is ethyl acetoacetate obtained from ethyl acetate ?
8 1
1

BKR—11076 2 NIR/KW/18/2080