
a) NaBH4
Interpretation:
The product obtained when the compound shown is treated with NaBH4; then with H3O+.
Concept introduction:
All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH4. Acids, esters and aldehydes yield a 10 alcohol upon reduction with LiAlH4, while ketones yield 20 alcohols. The reaction is carried out in ether solution as LiAlH4 reacts violently with water and explodes when heated above 120°C.
Esters will react with two molar equivalents of ethylmagnesium bromide to yield a 10 alcohol.
To give:
The products obtained when the compound shown is treated with NaBH4; then with H3O+.
b) LiAlH4
Interpretation:
The product obtained when the compound shown is treated with LiAlH4; then with H3O+.
Concept introduction:
Aldehydes and ketones can be reduced to alcohols using NaBH4. It reduces the esters very slowly and does not reduce carboxylic acids. The reduction can be carried out in either water or alcohol solution.
All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH4. Acids, esters and aldehydes yield a 10 alcohol upon reduction with LiAlH4, while ketones yield 20 alcohols. The reaction is carried out in ether solution as LiAlH4 reacts violently with water and explodes when heated above 120°C.
Esters will react with two molar equivalents of ethylmagnesium bromide to yield a 10 alcohol.
To give:
The products obtained when the compound shown is treated with LiAlH4; then with H3O+.
c) 2 CH3CH2MgBr
Interpretation:
The product obtained when the compound shown is treated with 2 CH3CH2MgBr; then H3O+.
Concept introduction:
Aldehydes and ketones can be reduced to alcohols using NaBH4. It reduces the esters very slowly and does not reduce carboxylic acids. The reduction can be carried out in either water or alcohol solution.
All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH4. Acids, esters and aldehydes yield a 10 alcohol upon reduction with LiAlH4, while ketones yield 20 alcohols. The reaction is carried out in ether solution as LiAlH4 reacts violently with water and explodes when heated above 120°C.
Esters will react with two molar equivalents of ethylmagnesium bromide to yield a 10 alcohol.
To give:
The products obtained when the compound shown is treated with 2 CH3CH2MgBr; then H3O+.

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Chapter 17 Solutions
Organic Chemistry
- What is the name of the following compound? SiMe3arrow_forwardK Draw the starting structure that would lead to the major product shown under the provided conditions. Drawing 1. NaNH2 2. PhCH2Br 4 57°F Sunny Q Searcharrow_forward7 Draw the starting alkyl bromide that would produce this alkyne under these conditions. F Drawing 1. NaNH2, A 2. H3O+ £ 4 Temps to rise Tomorrow Q Search H2arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning

