Chemistry Aldehydes & Ketones MDCAT 2013
PMDC Verified Question 85 of 94
What is the structure of alcohol which on oxidation with acidified \( Na_2Cr_2O_7 \) gives \( C_6H_5-CO-CH_3 \)?
A
\( C_6H_5-CH_2CH_2OH \)
B
\( C_6H_5-CH(OH)CH_3 \)
C
\( C_6H_4(OH)-CH_2CH_3 \)
D
\( C_6H_5-C(OH)(CH_3)_2 \)
Tap any option to test your recall and reveal the step-by-step Propolis autopsy.

Propolis Cognitive Error Autopsy

Official Correct Choice:
Option B: \( C_6H_5-CH(OH)CH_3 \)
Concept:

Ketones are produced strictly by the oxidation of secondary alcohols.

Solution:

  • The target product is acetophenone, \( C_6H_5-CO-CH_3 \), which is a ketone.


  • To form this ketone, the precursor must be a secondary alcohol with the exact same carbon skeleton.


  • Option B, 1-phenylethanol (\( C_6H_5-CH(OH)CH_3 \)), is a secondary alcohol. Oxidation removes the two hydrogen atoms from the \( CH-OH \) unit to form the \( C=O \) double bond.


Why other options are incorrect:

Option A is a primary alcohol and would oxidize to a carboxylic acid. Option C is a phenol derivative. Option D is a tertiary alcohol, which strongly resists oxidation.

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