The following dihaloalkanes gives an N-(haloalkyl)phthalimide on reaction with one equivalent of the potassium salt of phthalimide. Deduce the structure of the phthalimide derivative formed:

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Both A and B in equal proportions

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Neither A nor B are formed. An elimination product is formed rather.

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Solution

The correct option is A

If you look at the potassium salt of phthalimide, the nitrogen part, with its negative charge, is a capable nucleophile. This charge is stabilized by the presence of the two electron-withdrawing carbonyl groups on either side of the nitrogen anion. But it is a nucleophile nevertheless:

As shown above, the nucleophile attacks the carbon bearing the better leaving group. In general, Bromine is a much better leaving group than Fluorine in nucleophilic substitutions. The Bromide might form KBr depending on the nature of the solvent.

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The following dihaloalkanes gives an N-(haloalkyl)phthalimide on reaction with one equivalent of the potassium salt of phthalimide. Deduce the structure of the phthalimide derivative formed:

Pthalamide on treatment with ethanolic potassium hydroxide forms potassium salt of phthalimide which on heating with alkyl halide followed by alkaline hydrolysis produces the corresponding amine. This reaction is known as:

Q. (a) Write the reactions involved in the following:

(i) Hoffmann bromamide degradation reaction

(ii) Diazotisation

(iii) Gabriel phthalimide synthesis

(b) Give reasons :

(i)

(C H_{3})_{2} N H

is more basic than

(C H_{3})_{3} N

in an aqueous solution.

(ii) Aromatic diazonium salts are more stable than aliphatic diazonium salts.

Q. Match the column I with column II and mark the appropriate choice.

	Column I		Column II
(A)	Aniline	(i)	Can be made by Gabriel phthalimide reaction
(B)	N-Methylaniline	(ii)	Undergoes electrophilic substitution reaction with $H N O_{2}$
(C)	N, N-Dimethylaniline	(iii)	Forms yellow oily product with $H N O_{2}$
(D)	Benzylamine	(iv)	Gives azo dye test

Q. An alkene (A)

C_{16} H_{16}

on ozonolysis gives only one product (B)

C_{8} H_{8 O}

. Compound (B) on reaction with

N a O H / I_{2}

yields sodium benzoate. Compound (B) reacts with

K O H / N H_{2} N H_{2}

yielding a hydrocarbon (C)

C_{8} H_{10}

. Write the structures of compounds (B) and (C). Based on this information two isomeric structures can be proposed for alkene (A). Deduce their structures. The isomer of (A) which on catalytic hydrogenation (

H_{2} / P d - C

) gives a racemic mixture is:

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