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An organic compound X(C(4)H(9)Br) on tre...

An organic compound `X(C_(4)H_(9)Br)` on treatment with alc, KOH gave isomeric product with the formula `C_(4)H_(8)`. On ozonolysis one of these gave only product `CH_(3)CHO` while the other gave two

A

2-bromobutane

B

2-bromopentane

C

1,2-dibromo butane

D

3-bromopentene

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem, we need to identify the organic compound \( X \) with the formula \( C_4H_9Br \) that, upon treatment with alcoholic KOH, yields isomeric products with the formula \( C_4H_8 \). We also know that one of these products gives only acetaldehyde (\( CH_3CHO \)) upon ozonolysis, while the other gives two products. ### Step-by-Step Solution: 1. **Identify the Structure of Compound \( X \)**: - The compound \( X \) has the formula \( C_4H_9Br \). This indicates it is a brominated alkane with four carbon atoms. The possible structures for \( C_4H_9Br \) include: - 1-bromobutane - 2-bromobutane - 1-bromo-2-methylpropane - 2-bromo-2-methylpropane 2. **Reaction with Alcoholic KOH**: - When \( X \) reacts with alcoholic KOH, elimination occurs, leading to the formation of alkenes. The elimination can produce two isomeric alkenes from \( X \). - The possible alkenes from \( 2-bromobutane \) are: - 1-butene (\( CH_2=CH-CH_2-CH_3 \)) - 2-butene (\( CH_3-CH=CH-CH_3 \)) 3. **Ozonolysis of the Alkenes**: - Ozonolysis of alkenes involves the cleavage of the double bond and formation of carbonyl compounds. - For 1-butene: - Ozonolysis gives two moles of acetaldehyde (\( CH_3CHO \)). - For 2-butene: - Ozonolysis gives one mole of acetaldehyde (\( CH_3CHO \)) and one mole of propanal (\( CH_3CH_2CHO \)). 4. **Determine the Correct Alkyl Halide**: - Since one alkene gives only acetaldehyde and the other gives two products, we can conclude that the compound \( X \) must be 2-bromobutane. This is because: - 2-bromobutane leads to 1-butene (which gives two moles of acetaldehyde) and 2-butene (which gives acetaldehyde and propanal). 5. **Final Answer**: - Therefore, the compound \( X \) is \( 2-bromobutane \). ### Summary of Findings: - Compound \( X \) is \( 2-bromobutane \) (option A).
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