Which one of the following reagents can not cause $C - O$ bond fission in alcohols?

H C l / Z n C l_{2}

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P C l_{5}

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S O C l_{2}

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Sodium

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Solution

The correct option is D Sodium
Unlike other reagents which promote a substitution reaction, Na only abstracts the proton. Hence, no $C - O$ bond fission takes place.

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