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H(3)C-CH(2)-underset(O)underset(||)(C)-C...

`H_(3)C-CH_(2)-underset(O)underset(||)(C)-CH_(3)underset(D_(2)O)overset(NaBH_(4))to` Product ?

A

`H_(3)C-underset(H)underset(|)overset(OD)overset(|)(C)-CH_(2)-CH_(3)`

B

`H_(3)C-underset(D)underset(|)overset(OH)underset(|)(C)-CH_(2)-CH_(3)`

C

`H_(3)C-underset(D)underset(|)overset(OD)overset(|)(C)-CH_(2)-CH_(3)`

D

none

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem, we need to analyze the reaction step by step. The starting material is a ketone, and we will be reducing it using sodium borohydride (NaBH4) in the presence of deuterium oxide (D2O). Let's break down the process: ### Step 1: Identify the Reactants The starting material is: \[ \text{CH}_3\text{CH}_2\text{C}(\text{O})\text{CH}_3 \] This is a ketone (specifically, butan-2-one). ### Step 2: Reduction of the Ketone Sodium borohydride (NaBH4) is a reducing agent that will reduce the ketone to an alcohol. The mechanism involves the hydride ion (H-) from NaBH4 attacking the carbonyl carbon (C=O) of the ketone. The reaction can be represented as: \[ \text{CH}_3\text{CH}_2\text{C}(\text{O})\text{CH}_3 + \text{NaBH}_4 \rightarrow \text{CH}_3\text{CH}_2\text{C}(\text{OH})\text{CH}_3 \] ### Step 3: Formation of the Alcohol After the hydride attack, the carbonyl group is converted into a hydroxyl group (OH), resulting in: \[ \text{CH}_3\text{CH}_2\text{C}(\text{OH})\text{CH}_3 \] This is butan-2-ol. ### Step 4: Hydrolysis with D2O Now, we perform hydrolysis using deuterium oxide (D2O) instead of regular water. During this step, the hydroxyl group (OH) will be replaced by a deuterated hydroxyl group (OD). The reaction can be represented as: \[ \text{CH}_3\text{CH}_2\text{C}(\text{OH})\text{CH}_3 + \text{D}_2\text{O} \rightarrow \text{CH}_3\text{CH}_2\text{C}(\text{OD})\text{CH}_3 \] ### Step 5: Final Product The final product after the reaction with D2O will be: \[ \text{CH}_3\text{CH}_2\text{C}(\text{OD})\text{CH}_3 \] ### Conclusion The product of the reaction is: \[ \text{CH}_3\text{CH}_2\text{C}(\text{OD})\text{CH}_3 \] ### Matching with Options From the options given, we can conclude that the correct product corresponds to: - **Option 1: CH3ODCH2CH3**
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