Question

`[CH_(3)CH_(2)CH_(2)overset(+NMe_(3))overset(|)(CHCH_(3))]OHoverset(Delta)rarr`
The product obtained is .
A. `cis-CH_(3)CH_(2)CH=CHCH_(3)`
B. `trans-CH_(3)CH_(2)CH=CHCH_(3)`
C. `CH_(3)CH_(2)CH_(2)CH=CH_(2)`
D. a mixture of all of these

Answer 1

Correct Answer - D

Quaternary ammonium hydroxide unergoes Hofmann elimination to give the less substituted alkene (as the major product) resulting from loss of the more acidiec `beta (1^(@)gt2^(@) gt 3^(@)` This is the Hofman rule
Since the amine is a relatively poor leaving group the `TS` has more `C-H` bond -breaking than double bond formation or `NR_(3)` leaving Thus the acidity of the` betaH` becomes more important than the stability of the alkene that forms .