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Major product of the following reaction ...

Major product of the following reaction
`CH_(3)-CH_(2)-Broverset(KCN)tounderset(H_(2)O)overset(overline(O)H)tounderset(Delta)overset(PCl_(5))to` product

A

`CH_(3)-CH_(2)-Cl`

B

`H_(3)C-CH_(2)-underset(O)underset(||)(C)-Cl`

C

`CH_(3)-CH_(2)-CN`

D

`CH_(3)-underset(O)underset(||)(C)-NH_(2)`

Text Solution

AI Generated Solution

The correct Answer is:
To determine the major product of the reaction involving `CH3-CH2-Br` with `KCN`, followed by hydrolysis with `H2O`, and then treatment with `PCl5`, we can break down the steps as follows: ### Step-by-Step Solution: 1. **Identify the Starting Material**: The starting material is `CH3-CH2-Br` (ethyl bromide). Bromine is a good leaving group. **Hint**: Recognize that bromine can easily leave, allowing for nucleophilic substitution. 2. **Nucleophilic Substitution with KCN**: When `KCN` is added, the cyanide ion (`CN⁻`) acts as a nucleophile. It attacks the carbon atom bonded to bromine, leading to the displacement of bromine. The reaction can be represented as: \[ CH3-CH2-Br + KCN \rightarrow CH3-CH2-CN + KBr \] The major product at this stage is `CH3-CH2-CN` (ethyl cyanide). **Hint**: Remember that nucleophiles attack electrophilic centers, resulting in the substitution of the leaving group. 3. **Hydrolysis of Ethyl Cyanide**: Next, the product `CH3-CH2-CN` undergoes hydrolysis when treated with water (`H2O`). The cyanide group (`CN`) is converted into a carboxylic acid group (`COOH`). The reaction can be represented as: \[ CH3-CH2-CN + H2O \xrightarrow{H^+} CH3-CH2-COOH \] The product formed is `CH3-CH2-COOH` (propanoic acid). **Hint**: Hydrolysis involves the addition of water, which converts nitriles to carboxylic acids. 4. **Conversion to Acid Chloride with PCl5**: Finally, when `PCl5` is added to `CH3-CH2-COOH`, it converts the carboxylic acid into an acyl chloride. The reaction can be represented as: \[ CH3-CH2-COOH + PCl5 \rightarrow CH3-CH2-C(=O)Cl + POCl3 + HCl \] The major product of this step is `CH3-CH2-C(=O)Cl` (ethyl acyl chloride or ethanoic chloride). **Hint**: The reaction with PCl5 replaces the hydroxyl group of the carboxylic acid with a chlorine atom, forming an acid chloride. ### Final Product: The final major product of the entire reaction sequence is `CH3-CH2-C(=O)Cl`, which is ethyl acyl chloride.
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