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Consider the following sequence of reac...

Consider the following sequence of reactions
`C_(2)H_(5)C -= CH overset(CH_(3)MgBr)rarr A underset((2)H_(2)O^(+))overset((1)HCHO) rarr B`
The product `(B)` is

A

`CH_(3)CH_(2)OH`

B

`C_(2)H_(5)underset(CH_(3))underset(|)C-CHCH_(2)OH`

C

`C_(2)H_(5)C-=C-underset(OH)underset(|)CH-CH_(3)`

D

`C_(2)H_(5)C-=C-CH_(2)OH`

Text Solution

AI Generated Solution

The correct Answer is:
To determine the product B from the given sequence of reactions, let's analyze each step carefully. ### Step-by-Step Solution: 1. **Identify the Starting Material**: The starting material is a terminal alkyne, specifically 1-pentyne (C2H5C≡CH). 2. **Reaction with Grignard Reagent**: The terminal alkyne reacts with the Grignard reagent, CH3MgBr. In this reaction, the terminal alkyne acts as a nucleophile and attacks the electrophilic carbon of the Grignard reagent. This results in the formation of a new carbon-carbon bond. The product of this reaction (let's call it A) will be: \[ C_2H_5C \equiv C - CH_3 \quad \text{(1-pentyne reacts with CH3MgBr)} \] 3. **Formation of an Alkyne Alcohol**: The product A (which is now a magnesium alkoxide) will then react with formaldehyde (HCHO) in the presence of an acidic workup (H3O+). The nucleophilic carbon (from the alkyne) will attack the carbonyl carbon of formaldehyde, leading to the formation of an alkoxide intermediate. 4. **Protonation**: After the nucleophilic attack, the intermediate is protonated during the acidic workup, resulting in the formation of a secondary alcohol. The structure will be: \[ C_2H_5C(CO)H \quad \text{(where CO is the -OH group from the formaldehyde)} \] 5. **Final Product B**: The final product B can be represented as: \[ C_2H_5C(CH_2OH)C \quad \text{(which is 3-pentanol)} \] ### Conclusion: The product B is 3-pentanol.
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