Reduction of Pivalic acid?

2012-04-22 7:29 am
Can Pivalic acid be reduced to an alcohol, a tertiary alcohol
Explanation is appreciated

回答 (2)

2012-04-28 10:56 pm
✔ 最佳答案
Yes, you can turn pivalic acid into an alcohol.
No, you cannot turn pivalic acid into a tertiary alcohol.

Pivalic acid, or dimethylpropanoic acid, is a carboxylic acid. With strong reducing agents like LiAlH4, on can reduce an acid into respective parent alcohol, that is, 2,2-dimethylpropan-1-ol (neopentyl alcohol).

Notice that when acid is reduced, hydroxyl group is still attached to the alpha carbon which is originally where C=O locates:
R-COOH ------> R-CH2OH

Conversely speaking, only primary alcohol can be oxidized to give carboxylic acid; tertiary alcohol yields no acid. The reverse reaction should also apply.


圖片參考:http://imgcld.yimg.com/8/n/HA00075708/o/701204210094613873397100.jpg
2012-04-26 12:09 am
Lithium aluminium hydride is widely used in organic chemistry as a reducing agent.[3] It is more powerful than the related reagent sodium borohydride owing to the weaker Al-H bond compared to the B-H bond.[20] Often as a solution in diethyl ether and followed by an acid workup, it will convert esters, carboxylic acids , acyl chlorides, aldehydes, and ketones into the corresponding alcohols (see: carbonyl reduction). Similarly, it converts amide, nitro, nitrile, imine, oxime, and azide compounds into the amines (see: amide reduction).

AS LiAlH4 is a strong reducing agent, it can turn RCO2H into an alcohol.
1)LiAlH4 in dry ether
RCO2H ------------------------------> ROH
2)H30+


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