Question

1. Draw the Product of the Following Reactions: (5 marks) HO (CH3)2CHCH=CH2 - Η V + 2H— + 2H-Br - — 5.X- O CH3 D . AICI + H30 CM

Answer 1

Electrophilic addition of H+ to alkene gives a secondary carbocation which rearranges to more stable tertiary carbocation and then nucleophilic attack of water molecule gives an alcohol.

(CH3)2CH-CH=CH2 - + — сна I rearrangement. Ult31 — Нутно С (+) -Н, te+ 3 . . tartiary carbocation — (t, etta City

Successive addition of HBr with alkyne according to Markonickoff's rule gives a geminal dibromide.

م یر مولانا اسرار ا + CH3 geminal n. . 'dibromide 1 ا By :

First cyclohexyl iodide flipped to less stable axial conformer and then less hindered attack of the nucleophile acetate gives cyclohexyl acetate.

..må DMC s-coe a vetem SAG leyclohexyl iodide .) equatorial : conformer more stable m or --entz (swt) less hindered IZ approach axial conformer less stable suretz lcyclohexyl acetate )

This is a simple Diels Alder reaction and gives a substituted cyclohexene.

This a electrophilic substitution reaction, known as Friedel-Crafts alkylation. Since the acetyl group is meta directing hence the ethyl group added to the meta position.

CH greita .:-.AlCl3 resta Tiit CH₂ THE C.. Alla t A tott hens acats Htz Alca (firedel Craft . alkylation) election-withdrawing m-directing group. group, hence..