836 CHAPTER 19 Carbonyl Compounds III
- Indicate how each of the following compounds could be synthesized from the given starting material and any other necessary
reagents:
a. d.b. e.c. f.- Bupropion hydrochloride is an antidepressant marketed under the trade name Wellbutrin®. Propose a synthesis of bupropion
hydrochloride, starting with benzene. - What reagents would be required to carry out the following transformations?
- Give the products of the following reactions:
a.b.- a. Show how the amino acid alanine can be synthesized from propanoic acid.
b. Show how the amino acid glycine can be synthesized from phthalimide and diethyl 2-bromomalonate.CH 3 CHCO−O+NH
3
alanineCH 2 CO−O+NH
3
glycineCHCH+O OO OHO−2 CH 3 CH 2 OCCH 2 CH 2 COCH 2 CH 3O O- CH 3 CH 2 O−
- H 3 O+
O OCH CH CHCCH 3OCH CHCO−OCH CHCOCH 2 CH 3CCHCH 3
+NH
2 C(CH 3 ) 3 Cl−OClbupropion hydrochlorideO OO
(CH 2 ) 2 CH 3
CH 3 CH 2 OC(CH 2 ) 4 COCH 2 CH 3CCH 2 CH 3OCCH 2 CH 2 CH 2 COHOOO OOOCH 3 CCH 2 COCH 2 CH 3O OCH 3 CCH 2CH 3 C(CH 2 ) 3 COCH 3O O CH 3
CH 3OOOCH 3 CCH 3OOCH 3 CCH 2 CH