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Question

An unknown alkyl halide (A) reacts with alcoholic KOH to produce a hydrocarbon (C4H8). Ozonolysis of the hydrocarbon affords one mole of propionaldehyde and one mole of formaldehyde. Suggest which organic structure among the following is the correct structure of the above alkyl halide(A).

A
CH3(CH2)3Br
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B
CH3CH(Br)CH(Br)CH3
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C
CH3CH2CH(Br)CH3
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D
Br(CH2)4Br
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Solution

The correct option is A CH3(CH2)3Br
In dehydrohalogenation reaction, major product will be saytzeff product i.e. more substituted alkene.
Ozonolysis is the cleavage of an alkene or alkyne with ozone to form organic compounds in which the multiple carbon-carbon bond has been replaced by a double bond to oxygen.
1-butene on ozonolysis yields formaldehyde and propionaldehyde.
The formation of product is given below.
Thus alkyl halide (A) is bromobutane. Hence option (a) is correct.

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