Dolbier HW Solutions 390

Dolbier HW Solutions 390 - NaOD D 2 O Cyclopentanone O H H...

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
The third step is conversion of a vicinal bromohydrin to an epoxide in aqueous base. ( b ) The overall yield is the product of the yields of the individual steps. Yield 5 100(0.58 3 0.54 3 0.68) 5 21% 18.26 The product is a sul f de (thioether). Retrosynthetic analysis reveals a pathway that begins with ben- zene and acetic anhydride. The desired synthesis can be accomplished with the following series of reactions: The synthesis is completed by reacting bromomethyl phenyl ketone with 1-propanethiolate anion. 18.27 All these problems begin in the same way, with exchange of all the a protons for deuterium (Section 18.8).
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: NaOD D 2 O Cyclopentanone O H H H H Cyclopentanone-2,2,5,5-d 4 O D D D D KOH CH 3 CH 2 CH 2 SH CCH 2 SCH 2 CH 2 CH 3 O CCH 2 Br O CH 3 CH 2 CH 2 S 2 1-Propanethiol 1-Propanethiolate Phenyl (1-thiopropyl)-methyl ketone AlCl 3 Br 2 H 1 1 Benzene CH 3 COCCH 3 O O Acetic anhydride CCH 3 O Acetophenone CCH 2 Br O Bromomethyl phenyl ketone CCH 2 SCH 2 CH 2 CH 3 O CCH 2 Br 1 O SCH 2 CHCH 2 CH 3 2 CCH 3 O 1 O O CH 3 COCCH 3 (CH 3 ) 3 CCHCH 2 Br OH 1-Bromo-3,3-dimethyl-2-butanol KOH H 2 O 2-tert-Butyloxirane (68%) (CH 3 ) 3 CC CH 2 H O 484 ENOLS AND ENOLATES...
View Full Document

Ask a homework question - tutors are online