Be sure to answer all parts. select the three most acidic hydrogen atoms in lactic acid, ch3ch (oh) co2h, and rank them in order of decreasing acidity. explain your reasoning.

Question

Chemistry

Charlize Lloyd

11 August, 10:03

Be sure to answer all parts. select the three most acidic hydrogen atoms in lactic acid, ch3ch (oh) co2h, and rank them in order of decreasing acidity. explain your reasoning.

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Chana Chase · Answer 1

Lactic acid having the formula such as CH_3CH_2COOH

On loosing a proton from carboxyl group may result in carboxyl ion which get stablises by reasonanse and thus the hydrogen of carboxyl is more acidic.

Whereas, after loosing hydrogen from 2nd carbon result in secondary carbanion. The charge on secondary carbanion get increases high enough due to + I effect of methyl group and thus attracts the lost proton to it. Thus the hydrogen at 2nd carbon is least acidic.

The compound with formula CH_3CH (OH) COOH.

On loosing a proton from carboxyl group may result in carboxyl ion which get stablises by reasonanse and thus the hydrogen of carboxyl is more acidic.

But the hydroxyl group having high + I effect than methyl group due to which the secondary carbanion formed after removal of proton will again attracts the lost proton towards it due to higher negative charge on it. Hence, in this case as well 2nd carbon is least acidic.