Question 24.2: Lactic acid can be isolated from sour milk. Is lactic acid c......
Lactic acid can be isolated from sour milk. Is lactic acid chiral?
\quad\quad \ \ \ OH \ \ O\\ \quad\quad\quad| \ \ \ \ \ \ \parallel \\ \underset{3}{C}H_{3} – \underset{2}{C}H – \underset{1}{C}OH \quad\quad\quad \text{Lactic acid}STRATEGY
To find out if lactic acid is chiral, list the groups attached to each carbon, and see if any carbon is attached to four different groups.
Step-by-Step
\text{Groups on carbon 1} \quad\quad \text{Groups on carbon 2} \quad\quad \text{Groups on carbon 3}\\
1. -OH \quad\quad\quad\quad\quad\quad\quad 1. -CO_{2}H \quad\quad\quad\quad\quad 1. -CH(OH)CO_{2}H \\2. =O \quad\quad\quad\quad\quad\quad\quad \ \ \ 2. -OH \quad\quad\quad\quad\quad\quad \ 2. -H \\ 3. -CH(OH)CH_{3} \quad\quad \ \ 3. -H \quad\quad\quad\quad\quad\quad\quad 3. -H \\ \quad\quad\quad\quad\quad\quad\quad\quad\quad\quad\quad 4. -CH_{3} \quad\quad\quad\quad\quad\quad 4. -H
Of the three carbons, carbon 2 has four different groups, so lactic acid is chiral.
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