Arrange the following compounds in increasing order of their property as indicated :

Acetaldehyde, acetone, di-tert-butyl ketone, methyl torl-butyl ketone (reactivity towards HCN).

$C H_{3} C H_{2} C H (B r) C O O H, C H_{3} C H (B r) C H_{2} C O O H, (C H_{3})_{2} C H C O O H, C H_{3} C H_{2} C H_{2} C O O H {(a c i d s t r e n g t h)}$

Benzoic acid, 4 - nitrobenzoic acid, 3, 4 - dinitro benzoic acid, 4 - methoxy benzoic acid (acid strength).

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Solution

The reactivity of a compound depends on the steric hindrance due to the groups present around the carbonyl group. Greater the steric hindrance, less will be the reactivity of the compound. Reactivity towards HCN is in following order.

Di - tertiary butyl ketone < Methyl tertiary butyl ketone < Acetone < Acetaldehyde.

Alkyl group with +I effect decreasees the acidic strength whereas with -I effect increases the acidic strength -I effect decreases with distance.

Increasing order of acidic strength is

$(C H_{3})_{2} C H C O O H < C H_{3} C H_{2} C H_{2} C O O H < C H_{3} C H (B r) C H_{2} C O O H < C H_{3} C H_{2} C H (B r) C O O H$

Increasing order of acidic strength is

$(C H_{3})_{2} C H C O O H < C H_{3} C H_{2} C H_{2} C O O H < C H_{3} C H (B r) C H_{2} C O O H < C H_{2} C H_{2} C H (B r) C O O H$

Electron donating group ( $- O C H_{3}$ ) decreases the acidic strength where as electron withdrawing group $(N O_{2})$ increases the same.

Increasing order of acidic strength is :

4 - methoxy benzoic acid < benzoic acid < 4 - nitrobenzoic acid < 3, 4 - dinitrobenzoic acid.

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H C N

C H_{3} C H_{3} C H (B r) C O O H, C H_{3} C H (B r) C H_{2} C O O H, (C H_{3})_{2} C H C O O H

4 -

3, 4 -

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p-nitro benzoic acid, p-methoxy benzoic acid, and

benzoic acid

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