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When a nucleophile attack to carbonyl gr...


When a nucleophile attack to carbonyl group of a carboxylic acid derivative, the carbon-oxygen `pi`- bond breaks. The resulting intermediate is called a tetrahedral intermediate because `sp^(2)` carbon in the reactant has become a tetrahedral `(sp^(3))` carbon in the intermediate.
Here `overset(..)Y^(ɵ)` is leaving group, the weaker base is expelled preferentially.
Q. Which of the following given compounds don't form amide, when react with `CH_(3)COCl`.
(1). `CH_(3)-NH-CH_(3)`
(2). `CH_(3)-underset(CH_(3))underset(|)N-CH_(2)H_(5)`
(3).
(4). `CH_(3)-CH_(2)-CH_(2)-NH_(2)`

A

1 and 4

B

only (4)

C

2 and 3

D

only (1)

Text Solution

Verified by Experts

The correct Answer is:
B
Tertiary amine and pyridine doesn't from amides when react with `CH_(3)-underset(O)underset(||)C-Cl`
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Knowledge Check

  • The type of isomerism shown by the following compounds is CH_(3)CH_(2)CH_(2)CH_(2)CH_(3),CH_(3)-overset(CH_(3))overset(|)(C)H-CH_(2)CH_(3),CH_(3)-underset(CH_(3))underset(|)overset(CH_(3))overset(|)(C)-CH_(3)

    A
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    D
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    A
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    B
    `H_(5)C_(6)-overset(O)overset(||)(C)-H`
    C
    `CH_(3)-CH_(2)-OH`
    D
    `H-overset(O)overset(||)(C)-OH`

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