Which one of the following is not formed when acetone reacts with 2-pentanone in the presence of dilute NaOH followed by heating?
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Answer
(2) [figure]
Solution
Acetone CH3COCH3 forms an enolate at CH3; 2-pentanone CH3COCH2CH2CH3 forms enolates at C-1 (CH3) or C-3 (CH2). Aldol addition followed by heating gives α,β-unsaturated ketones.
(1) Acetone enolate + acetone (CH3)2C=CH-CO-CH3 (self condensation) — formed.
(3) Acetone enolate + 2-pentanone CH3CH2CH2-C(CH3)=CH-CO-CH3 — formed.
(4) C-3 enolate of 2-pentanone + acetone (CH3)2C=C(C2H5)-CO-CH3 — formed.
(2) C2H5-CO-C(CH3)=C(C2H5)2 contains an ethyl ketone unit C2H5-CO- and a pentan-3-one-derived =C(C2H5)2 unit; neither acetone nor 2-pentanone can supply these.
Compound (2) is not formed.
Answer: (2)