Portmess Homework Q&S 116

Portmess Homework Q&S 116 - CH 3 CCH 2 OH CH 3 CH 3...

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

View Full Document Right Arrow Icon
( e ) Elimination in 3-bromopentane will give the stereoisomers ( E )- and ( Z )-2-pentene. ( f ) Three alkenes can be formed from 2-bromopentane. 5.35 ( a ) The isomeric C 5 H 12 O alcohols are: ( b ) The order of reactivity in alcohol dehydration parallels carbocation stability and is tertiary . secondary . primary. The only tertiary alcohol in the group is 2-methyl-2-butanol. It will dehydrate fastest. ( c ) The most stable C 5 H 11 carbocation is the tertiary carbocation. ( d ) A proton may be lost from C-1 or C-3: CH 3 CH 3 CCH 2 CH 3 1 CH 3 H 2 C CCH 2 CH 3 CH 3 CH 3 C CHCH 3 1 1,1-Dimethylpropyl cation 2-Methyl-1-butene (minor alkene) 2-Methyl-2-butene (major alkene) 1,1-Dimethylpropyl cation CH 3 CCH 2 CH 3 CH 3 1 2-Methyl-2-butanol CH 3 CCH 2 CH 3 CH 3 OH 2,2-Dimethyl-1-propanol
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: CH 3 CCH 2 OH CH 3 CH 3 2-Methyl-1-butanol 3-Methyl-1-butanol 3-Methyl-2-butanol CH 3 CHCH 2 CH 2 OH CH 3 CH 3 CH 2 CHCH 2 OH CH 3 CH 3 CH OH CH 3 CHCH 3 CH 3 CH 2 CH 2 CH 2 CH 2 OH 1-Pentanol 2-Pentanol 3-Pentanol CH 3 CH 2 CHCH 2 CH 3 OH CH 3 CH 2 CH 2 CHCH 3 OH base E2 CH 3 CH 3 CH 3 CH 2 CH 3 CH 2 1 1 CH 3 CH 2 CH 2 CHCH 3 Br 2-Bromopentane 1-Pentene ( E )-2-Pentene ( Z )-2-Pentene CH 3 CH 2 CH 2 CH CH 2 base E2 CH 3 CH 3 CH 2 CH 3 CH 2 CH 3 CH 3 CH 2 CHCH 2 CH 3 1 Br 3-Bromopentane ( E )-2-Pentene ( Z )-2-Pentene 110 STRUCTURE AND PREPARATION OF ALKENES: ELIMINATION REACTIONS...
View Full Document

This note was uploaded on 09/20/2011 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