3-bromo 3-methylhexane reacts with aq. KOH to give racemic mixture of products. Identify the type…
Chemistry20253 marksShort answer
3-bromo 3-methylhexane reacts with aq. KOH to give racemic mixture of products.
(a)[1.0]
Identify the type of reaction mechanism.
(b)[1.0]
Draw the structure of the transition state intermediate.
(c)[1.0]
If Bromine is replaced by fluorine, will the reaction proceed faster or slowly? Give reason.
Answer
Answer (a)
Official answer key
$S_N1$
Answer (b)
Official answer key
3-methylhexan-3-yl cation:
The transition state/intermediate is the tertiary carbocation: a planar $\mathrm{C^+}$ bonded to $\mathrm{CH_3}$, $\mathrm{CH_3CH_2}$ and $\mathrm{CH_2CH_2CH_3}$.
Carbocation with positively charged carbon attached to CH3, CH3CH2 and CH2CH2CH3.
Answer (c)
Official answer key
The reaction will become slow due to higher bond dissociation energy of C-F bond.
Check your working with the IUPAC name to structure: draw the structure of an organic compound from its IUPAC name, with formula and functional groups.