Which of these would be best to convert pentanal into 2-hexanol? CH3MgBr then H3O+ O NaBH4 CH3OH, H+ CH3CI, AICI3 O (CH3)2CuLi then H3O+

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Chapter1: Chemical Foundations
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**Question:**

Which of these would be best to convert pentanal into 2-hexanol?

**Options:**

- ○ CH₃MgBr then H₃O⁺
- ○ NaBH₄
- ○ CH₃OH, H⁺
- ○ CH₃Cl, AlCl₃
- ○ (CH₃)₂CuLi then H₃O⁺

**Explanation:**

This question involves the conversion of pentanal (an aldehyde) to 2-hexanol (an alcohol) using different reagents. For such conversions:

1. **CH₃MgBr then H₃O⁺**: This is a Grignard reaction where CH₃MgBr adds a methyl group to the carbonyl carbon followed by acid workup to produce an alcohol. This method can convert an aldehyde to a secondary alcohol.
   
2. **NaBH₄**: This reagent is used for the reduction of aldehydes and ketones to alcohols but will not extend the carbon chain.

3. **CH₃OH, H⁺**: Typically used in acetal formation with aldehydes; not applicable for the desired transformation.

4. **CH₃Cl, AlCl₃**: Used in Friedel-Crafts alkylation for aromatic compounds; not applicable for converting aldehydes to alcohols.

5. **(CH₃)₂CuLi then H₃O⁺**: A Gilman reagent (lithium diorganocopper) which can be used for conjugate additions, but not typically used to convert aldehydes to alcohols with chain extension.

The most effective method for this transformation would be option 1, using the Grignard reagent CH₃MgBr then H₃O⁺, which will involve adding a methyl group to pentanal, producing 2-hexanol.
Transcribed Image Text:**Question:** Which of these would be best to convert pentanal into 2-hexanol? **Options:** - ○ CH₃MgBr then H₃O⁺ - ○ NaBH₄ - ○ CH₃OH, H⁺ - ○ CH₃Cl, AlCl₃ - ○ (CH₃)₂CuLi then H₃O⁺ **Explanation:** This question involves the conversion of pentanal (an aldehyde) to 2-hexanol (an alcohol) using different reagents. For such conversions: 1. **CH₃MgBr then H₃O⁺**: This is a Grignard reaction where CH₃MgBr adds a methyl group to the carbonyl carbon followed by acid workup to produce an alcohol. This method can convert an aldehyde to a secondary alcohol. 2. **NaBH₄**: This reagent is used for the reduction of aldehydes and ketones to alcohols but will not extend the carbon chain. 3. **CH₃OH, H⁺**: Typically used in acetal formation with aldehydes; not applicable for the desired transformation. 4. **CH₃Cl, AlCl₃**: Used in Friedel-Crafts alkylation for aromatic compounds; not applicable for converting aldehydes to alcohols. 5. **(CH₃)₂CuLi then H₃O⁺**: A Gilman reagent (lithium diorganocopper) which can be used for conjugate additions, but not typically used to convert aldehydes to alcohols with chain extension. The most effective method for this transformation would be option 1, using the Grignard reagent CH₃MgBr then H₃O⁺, which will involve adding a methyl group to pentanal, producing 2-hexanol.
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