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Which of the following compounds requires an oxidizing agent for its preparation from 1-butanol?

1. CH3CH2CH2CH2Br
2. CH3CH2CH2CH = O
3. (CH3CH2CH2)2O
4. CH3-CH2-CH=CH2

Correct answer: CH3CH2CH2CH = O

Solution

Converting 1-butanol to butanal (CH3CH2CH2CHO) is an oxidation and requires a mild oxidizing agent (e.g. PCC). The others (bromide, ether, alkene) are made by substitution/dehydration and need no oxidant.

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