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Chapter 4: Problem 82

Reaction of an alkyl halide (A) with alcoholic KOH forms a product which on ozonolysis gives a mixture of propanone and methanal. The structure of the alkyl halide (A) is (a) 2 -Bromobutane (b) 1,4 -Dibromobutane (c) 2 -Bromo-2-methyl propane (d) 2,3 -Dibromobutane

Short Answer

Expert verified
The correct structure of alkyl halide (A) is 2-Bromo-2-methylpropane (option c). This is based upon the elimination (E2) reaction with alcoholic KOH, forming 2-Methylpropene as a product. Upon ozonolysis, the products obtained are propanone and methanal, which matches the provided information.

Step by step solution

01

Option (a): 2-Bromobutane

Let's first consider the reaction of 2-Bromobutane with alcoholic KOH. This reaction involves an elimination (E2) reaction, which will remove a proton on the carbon adjacent to the carbon with the bromine atom, resulting in a double bond. The product formed will be 2-Butene. Upon ozonolysis of 2-Butene, we get ethanal and ethanal, which is not propanone and methanal. So, option (a) is incorrect.
02

Option (b): 1,4-Dibromobutane

When 1,4-Dibromobutane reacts with alcoholic KOH, an elimination (E2) reaction occurs, leading to the formation of trans-2-Butene and BrCH2CH2Br as the product. Upon ozonolysis of trans-2-Butene, we get ethanal and ethanal again, which is not propanone and methanal. So, option (b) is incorrect too.
03

Option (c): 2-Bromo-2-methylpropane

When 2-Bromo-2-methylpropane reacts with alcoholic KOH, an elimination (E2) reaction occurs, leading to the formation of 2-Methylpropene as the product. Upon ozonolysis of 2-Methylpropene, we get propanone and methanal, which matches the given condition. So, option (c) is the correct structure of alkyl halide (A).
04

Option (d): 2,3-Dibromobutane

For the sake of completion, let's consider the reaction of 2,3-Dibromobutane with alcoholic KOH. An elimination (E2) reaction occurs, and we get 2,3-Dibromo-2-butene as the product. Upon ozonolysis of 2,3-Dibromo-2-butene, we get 1,3-dibromoacetone, ethanal and HBr, which is not propanone and methanal. So, option (d) is incorrect. Based on our analysis, the structure of alkyl halide (A) is 2-Bromo-2-methylpropane, making option (c) the correct answer.

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