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Question
Which of the following compound will most readily give a cyclic product when treated with a base ?
Which of the following compound will most readily give a cyclic product when treated with a base ?
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Solution
The correct option is C
Diesters on reacting with strong base undergoes intramolecular condensation reaction to give a cyclic β-keto ester product. This reaction is called Dieckmann condensation reaction.
The enolate ion formed at alpha carbon of one ester group will attack the electrophilic carbon of other ester group to form stable cyclic product.
Five membered ring are stable than four membered ring.
Compound (a) and (b) form 4 membered ring while (c) and (d) forms five membered rings.
Comparing (c) and (d), electrophilicity of carbon of ester in (d) is reduced due to presence of +I group (methyl) at α− carbon. Hence, it will react relatively slow compared to (c).
Diesters on reacting with strong base undergoes intramolecular condensation reaction to give a cyclic β-keto ester product. This reaction is called Dieckmann condensation reaction.
The enolate ion formed at alpha carbon of one ester group will attack the electrophilic carbon of other ester group to form stable cyclic product.
Five membered ring are stable than four membered ring.
Compound (a) and (b) form 4 membered ring while (c) and (d) forms five membered rings.
Comparing (c) and (d), electrophilicity of carbon of ester in (d) is reduced due to presence of +I group (methyl) at α− carbon. Hence, it will react relatively slow compared to (c).
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