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Which of the following compounds shall not produce propene by reaction with HBr followed by elimination or direct only elimination reaction?
A
$H_2C=C=O$
B
$H_3C-CH_2-CH_2Br$
C
Cyclopropane
D
$H_3C-CH_2-CH_2OH$
Explanation
Ketene gives acetyl bromide, not propene.
Detailed Solution
Cyclopropane $\xrightarrow{HBr} CH_3CH_2CH_2Br \xrightarrow{Elimination} CH_3-CH=CH_2$
$CH_3CH_2CH_2OH \xrightarrow{HBr} \xrightarrow{Elimination} CH_3-CH=CH_2$
$CH_2=C=O \xrightarrow{HBr} H_2C=C(Br)-OH \rightleftharpoons CH_3-CO-Br$ (no propene)
$CH_3CH_2CH_2Br \xrightarrow{Elimination} CH_3-CH=CH_2$
$CH_3CH_2CH_2OH \xrightarrow{HBr} \xrightarrow{Elimination} CH_3-CH=CH_2$
$CH_2=C=O \xrightarrow{HBr} H_2C=C(Br)-OH \rightleftharpoons CH_3-CO-Br$ (no propene)
$CH_3CH_2CH_2Br \xrightarrow{Elimination} CH_3-CH=CH_2$