Chemistry Paper V Organic Chemistry Previous Year Question Paper Year 2006 : IInd Year

Q. 1. (a) The compound A, C7 H8, on treatment with methylchloride and aluminium chloride, yields a mixture of two isomers B and C, C8 H10, which are oxidized by potassium permanganate to the isomeric acids D and E, C8 H6 O4, respectively. Whereas D is unaffected by heat, E gives F, C8 H4 O3. What are the structures of the compounds involved ? 5

(b) Convert
(i) p-MeCOC6H4CO2H—> p-MeCHOHC6H4 COOH
(ii) Ph. H –> 4-NH2 – 2 – OH – benzoic acid.
Answer :

Q. 2. (a) Draw the Fischer projection formulae for :
(i) (R) -3-methyI pentan-l~O|
(ii) (R)-3-methoxy-2-methylpropan-l-0| 2

(b) Predict the product of each of the following reactions :
(i) CH2 = CHCOOH + H2 / Ni -> ?

Image no.7

(c ) Write out the possible isomers of the aromatic compound, C7 H7 Cl. What would each give on oxidation ?
Answer :

Q. 3. Discuss the reaction mechanism of:
(i) Hoesch condensation
(ii) Ester hydrolysis
(iii) Wurtz reaction
Answer :

Q. 4. (a) Write a short note on Keto-enol tautomerism. 2
(b) Starting from diethyl-malonate, how will you prepare the following:
(i) 4-Methylpentanoic acid,
(ii) α-Methylsuccinic acid

(c ) Suggest what A and B could be in the reaction :

Image no.8
Answer :

Q. 5. (a) Discuss the isomerism exhibited by maleic and fumasic acids.

(b) Draw conformational isomers of cyclohexane. Which form is more stable ?

(c ) What happens when :
(i) Glycerol is treated with HI.
(ii) Citric acid is heated with cone. HjSO4.
Answer :

Q. 6- (a) 2,6-Di-t-butylphenol is a much weaker acid than phenol. Explain.

(b) How will you prepare the following :
(i) m-nitroaniline from benzene
(ii) Phenol from aniline. 2

(c ) Discuss the directive influence of-CHO and -NH2 groups in aromatic electrophilic substitution reaction.
Answer :

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