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CH(3)CH(2)-underset(CH(3))underset(|)(CH...

`CH_(3)CH_(2)-underset(CH_(3))underset(|)(CH)-CH_(2)-O-CH_(2)CH_(3)+HIto `?
The product is

A

`CH_(3)CH_(2)-underset(CH_(3))underset(|)(CH)-CH_(2)OH+CH_(3)CH_(2)I`

B

`CH_(3)-CH_(2)-underset(CH_(3))underset(|)(CH)-CH_(2)I+CH_(3)CH_(2)OH`

C

`CH_(3)-CH_(2)-underset(CH_(3))underset(|)(CH)-CH_(2)l+CH_(3)-I`

D

`CH_(3)-CH_(2)-OH` only

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem of the reaction of the ether \( CH_3CH_2-CH(CH_3)-CH_2-O-CH_2CH_3 \) with HI, we can follow these steps: ### Step 1: Identify the Structure of the Ether The given ether can be represented as: \[ CH_3CH_2-CH(CH_3)-CH_2-O-CH_2CH_3 \] This is an unsymmetrical ether because the two alkyl groups attached to the oxygen atom are different. ### Step 2: Understand the Reaction with HI When ethers react with hydrogen iodide (HI), they undergo cleavage. The reaction typically results in the formation of an alcohol and an alkyl halide. The cleavage occurs at the ether bond, breaking it into two parts. ### Step 3: Determine the Mechanism The reaction proceeds via an SN2 mechanism, especially for unsymmetrical ethers. In this mechanism, the nucleophile (I⁻ from HI) attacks the less sterically hindered carbon atom adjacent to the ether oxygen. ### Step 4: Identify the Alkyl Groups In our ether: - The left side has the alkyl group \( CH_3CH_2-CH(CH_3)-CH_2 \) (which is more sterically hindered). - The right side has the alkyl group \( CH_2CH_3 \) (which is less sterically hindered). ### Step 5: Cleavage of the Ether The I⁻ ion will preferentially attack the less hindered side (the ethyl group \( CH_2CH_3 \)). Therefore, the ether bond will break, leading to: - Formation of an alcohol from the more hindered side. - Formation of an alkyl halide from the less hindered side. ### Step 6: Write the Products After the cleavage: 1. The alcohol formed will be: \[ CH_3CH_2-CH(CH_3)-CH_2-OH \] (which is butanol) 2. The alkyl halide formed will be: \[ CH_3CH_2I \] (ethyl iodide) ### Final Products The final products of the reaction are: - Alcohol: \( CH_3CH_2-CH(CH_3)-CH_2OH \) (butanol) - Alkyl Halide: \( CH_3CH_2I \) (ethyl iodide) ### Summary The products of the reaction of the given ether with HI are: \[ CH_3CH_2-CH(CH_3)-CH_2OH + CH_3CH_2I \] ---
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