PistonFan531

10+ Year Member
Jun 23, 2008
294
1
Status
Pharmacist
1. Which is more stable, (Ch3)3C+ or (CH3)2(CF3)C+? Why?

2. Which C4H10O isomer do you expect to have the higher boiling point, CH3CH2OCH2CH3 or CH3CH2CH2CH2OH? Why?
 

rycetrix

10+ Year Member
May 12, 2008
399
3
Status
Pharmacist
1. (CH3)3C+ is more stable than (CH3)2(CF3)C+. CF3 groups are EWG (electron withdrawing groups). The CH3 groups are EDG (electron donating groups) which help stabilize the carbocation. Electrons are negative which make the carbocation less positive, thus stabilizing it. If you have EWG's instead, you lose that donation of electrons to stabilize the carbocation.

2. Go to the link to find the answer:
http://chemed.chem.purdue.edu/genchem/topicreview/bp/2organic/alcohols.html#vs
 
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