(a) Write the step and conditions involved in the following conversions:
 (i) Acetophenone to 2-phenyl-2-butanol
(ii) Propene to acetone
(b) Describe simple chemical tests to distinguish between the following pairs of compounds:
 Diethyl ether and Propanol

3

(a)

How will you carry out the following conversions:
(i) Acetone to chloroform?
(ii) Acetylene to Acetic acid?

3

(a)

Why is carboxyl group in benzoic acid meta directing?  Support your answer with two examples.

3

(a)

An aliphatic compound 'A' with a molecular formula of C₃H₆O reacts with phenylhydrazine to give compound 'B'.  Reaction of 'A' with I₂ in alkaline medium on warming, gives a yellow precipitate 'C'.  Identify the compounds A, B and C.

3

(a)

Write chemical reactions to affect the following transformations:
(a) Butan-1-ol to butanoic acid
(b) Benzyl alcohol to phenylethanoic acid
(c) 3-Nitrobromobenzene to 3-nitrobenzoic acid
(d) 4-Methylacetophenone to benzene-1, 4-di-carboxylic acid
(e) Cyclohexene to hexane-1,6-dioic acid
(f) Butanal to butanoic acid.

3

(a)

How will you bring about the following conversions in not more than two steps?
(i) Propanone to Propene
(ii) Ethanol to 3-Hydroxybutanal
(iii) Benzaldehyde to Benzophenone

3

(a)

Why are aliphatic carboxylic acids stronger acids than phenols?

3

(a)

Can Gattermann-Koch reaction be considered simular to Friedel-Crafts acylation? Discuss

3

(a)

Give the structure of the following compounds.
(i) 4-Nitropropiophenone
(ii) 2-Hydroxycyclopentanecarbaldehyde
(iii) Phenyl acetaldehyde

3

(a)

Write IUPAC names of the following structures.

3

(a)

Complete the following reaction sequence.

3

(a)

An alkene 'A' (Mol.  formula C₅H₁₀) on ozonolysis gives a mixture of two compounds 'B' and 'C'.  Compound 'B' gives positive Fehling's test and also forms iodoform on treatment with I₂ and NaOH.  Compound 'C' does not give Fehling's test but forms iodoform.  Identify the compounds A, B and C.  Write the reaction for ozonolysis and formation of iodoform from B and C.

3

(a)

An aromatic compound 'A' (Molecular formula C₈H₈O) gives positive 2, 4-DNP test.  It gives a yellow precipitates of compound 'B' on treatments with iodine and sodium hydroxide solution.  Compound 'A' does not give Tollen's or Fehling's test.  On drastic oxidation with potassium permanganate it forms a carboxylic acid 'C' (Molecular formula C₇HO)₆O₂),  which is also formed along with the yellow compound in the above reaction.  Identify A, B and C write all the reacitons involved.

3

(a)