TigerLilies

Senior Member
10+ Year Member
5+ Year Member
Jul 5, 2004
280
0
Status
what's the product(s) of potassium tbutoxide and 3-bromo-1-octene?
 

anon-y-mouse

Senior Member
10+ Year Member
Nov 14, 2005
1,382
13
Status
Resident [Any Field]
You can do this on your own... K-tertbutoxide, hmm, BULKY BULKY *base*... what's going to happen? Check your SN1/SN2/E1/E2 criteria.
 

TigerLilies

Senior Member
10+ Year Member
5+ Year Member
Jul 5, 2004
280
0
Status
anon-y-mouse said:
You can do this on your own... K-tertbutoxide, hmm, BULKY BULKY *base*... what's going to happen? Check your SN1/SN2/E1/E2 criteria.
I am confused. :(
 
About the Ads

Cooolguy

Senior Member
10+ Year Member
7+ Year Member
Jul 17, 2005
232
0
Status
Remember, a bulky base will lead you to something sexy
 
D

davie85

You have two possible reactions that could occur. The first and the least likely route is the formation of an ether by way of Williamson Ether Synthesis (SN2 displacement of bromide). This type of reaction occurs most readily with primary alkyl halides due to minimal steric interference. The second and most probable pathway that can be followed is deprotonation of one of the protons on carbon 4 with simultaneous explusion of bromide (E2). The driving force for this E2 elimination comes from forming a conjugated pi system. The double bond formed is of the trans or "E" configuration. The cis or "Z" double bond is unlikely to form in any significant amount because the reaction would have to proceed through a transition state of higher energy.
 
About the Ads