Dolbier HW Solutions 238

Dolbier HW Solutions 238 - one or more sp 3 carbon atoms....

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

View Full Document Right Arrow Icon
232 CONJUGATION IN ALKADIENES AND ALLYLIC SYSTEMS The allylic radical formed in the f rst step abstracts a bromine atom from Br 2 in the second propa- gation step. 10.5 Write both resonance forms of the allylic radicals produced by hydrogen atom abstraction from the alkene. Both resonance forms are equivalent, and so 2,3,3-trimethyl-1-butene gives a single bromide on treatment with N -bromosuccinimide (NBS). Hydrogen atom abstraction from 1-octene gives a radical in which the unpaired electron is delocalized between two nonequivalent positions. Allylic bromination of 1-octene gives a mixture of products 10.6 ( b ) All the double bonds in humulene are isolated, because they are separated from each other by
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: one or more sp 3 carbon atoms. Humulene CH 3 CH 3 H 3 C CH 3 CH 2 CHCH 2 (CH 2 ) 4 CH 3 1 BrCH 2 CH CH(CH 2 ) 4 CH 3 CH 2 CHCH(CH 2 ) 4 CH 3 Br NBS 1-Octene 3-Bromo-1-octene 1-Bromo-2-octene (cis and trans) CH 2 CHCH 2 (CH 2 ) 4 CH 3 1-Octene CH 2 CHCH(CH 2 ) 4 CH 3 CH 2 CH CH(CH 2 ) 4 CH 3 NBS (CH 3 ) 3 CC CH 2 CH 3 2,3,3-Trimethyl-1-butene (CH 3 ) 3 CC CH 2 CH 2 Br 2-(Bromomethyl)-3,3-dimethyl-1-butene (CH 3 ) 3 CC CH 2 CH 3 2,3,3-Trimethyl-1-butene (CH 3 ) 3 CC CH 2 CH 2 (CH 3 ) 3 CC CH 2 CH 2 1 3-Bromocyclohexene Bromine atom 1 2-Cyclohexenyl radical Bromine H H Br Br Br Br...
View Full Document

Ask a homework question - tutors are online