Question

mation shown below requires at least two steps. Provide the reagents/conditions for each & Each transformatie transformation. (20 pts) Reagents A-? Reagents ? Reagents D? Reagents .....: Reagents ? 6. Predict the product from the Birch reduction shown below: (3 pts) N2, NH3 CH, OH Bonus: (6 pts) Provide a synthesis for the target molecule using benzene.

Answer 1

SCHE 1) iso-Pr-Br + FeBr3 H2CCH; 2) H2/Ni Br2 + FeBr3 CH S3 CH3 CH2Br2 + FeBr3 1) n-Pr-Br + FeBr3 1)HNO3 +H2SO4 2) Sn/HCI CH3 CH NH2

A) -S-CH3 is ortho-para directing group. Bromination occurs at ortho position predominantly in presence of FeBr3 Lewis acid catalyst via aromatic electrophilic substitution. B) n-Propyl group is a bulky group and hence Fridel-Craft alkylation does not happen at ortho position, instead it happens at par apositon predominantly. C) Nitration as well happens at para position. And the reduciton of nitro group to give aniline. D) Fridel-Craft alkylation happens at para position. E) First the F-C alkylation at para position and then reduction of benzene ring. CN NC Na, NH3 CH3OH NC O CN H3C CH3 H2C1 CH3 Brich reduction always gives meta protonation product.

CH3 CH3 Na in liq. NH3 1 eq. mCPBA 1) iPr-MgBr names for OBA the money on yo ur , moren, of mCPBA CH3 - 2) H30+ CH O cyclohexa-1,4-diene OH 1)Me-MgBr 2) H30+ Via Brich reduction of benzene we get cyclohexa-1,4-diene. One of the C=C is epoxidized and then ring is opened with Grignard reagent to get anti addition. Further next C=C is epoxidized and ring it opened with another grignard reagent to give another anti addition, mCPBA is an epoxidizing agent, meta-chloroperbenzoic acid. CH3 HO, H2C OH