Dolbier HW Solutions 222

Dolbier HW Solutions 222 - 216 ALKYNES The desired...

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

View Full Document Right Arrow Icon
The desired intermediate, 1-butyne, is available by halogenation followed by dehydrohalo- genation of 1-butene. Reaction of the anion of 1-butyne with ethyl bromide completes the synthesis. ( b ) Dehydrohalogenation of 1,1-dichlorobutane yields 1-butyne. The synthesis is completed as in part ( a ). ( c ) 1-Butyne is converted to 3-hexyne as in part ( a ). 9.25 A single dehydrobromination step occurs in the conversion of 1,2-dibromodecane to C 10 H 19 Br. Bromine may be lost from C-1 to give 2-bromo-1-decene. Loss of bromine from C-2 gives ( E )- and ( Z )-1-bromo-1-decene. 9.26 ( a ) ( b ) ( c ) CH 3 CH 2 CH 2 CH 2 CC H NH 3 Li CH 3 CH 2 CH 2 CH 2 CH CH 2 1-Hexyne 1-Hexene CH 3 CH 2 CH 2 CH 2 C 1-Hexyne 1 CH H 2 Lindlar Pd CH 3 CH 2 CH 2 CH 2 CH 1-Hexene CH 2 CH 3 CH 2 CH 2 CH 2 C 1-Hexyne 1 CH 2H 2 Pt CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 Hexane Br BrCH 2 CH(CH 2 ) 7 CH 3 1,2-Dibromodecane
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

This note was uploaded on 09/26/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

Ask a homework question - tutors are online