Chemistry Aldehydes & Ketones MDCAT 2014
PMDC Verified Question 84 of 94
For the reaction:

$$ \text{?} + HCN \xrightarrow{\text{Base}} (CH_3)_2C(OH)CN $$
A
\( C_2H_5COCH_3 \)
B
\( CH_3COCH_3 \)
C
\( C_2H_5CH(CH_3)OH \)
D
\( C_2H_5CH_2CHO \)
Tap any option to test your recall and reveal the step-by-step Propolis autopsy.

Propolis Cognitive Error Autopsy

Official Correct Choice:
Option B: \( CH_3COCH_3 \)
Concept:

The addition of hydrogen cyanide (\( HCN \)) to a carbonyl compound yields a cyanohydrin. By examining the alkyl groups on the central carbon of the product, we can deduce the original carbonyl reactant.

Solution:

  • The product given is \( (CH_3)_2C(OH)CN \).


  • In a cyanohydrin, the central carbon was originally the carbonyl carbon (\( C=O \)).


  • By removing the \( -OH \) proton and the \( -CN \) group to reform the \( C=O \) bond, we are left with the two groups attached to that carbon: two methyl groups (\( CH_3 \)).


  • The carbonyl compound consisting of a carbonyl group bonded to two methyl groups is Acetone (\( CH_3COCH_3 \)).


Why other options are incorrect:

If option A (2-butanone) were used, the product would have one ethyl and one methyl group. Option C is an alcohol, which doesn't react with HCN. Option D is an aldehyde, which would yield a cyanohydrin with an ethyl group.

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