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Topic: Assistance with Zaitsev rule.  (Read 6451 times)

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Offline NewtoAtoms

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Assistance with Zaitsev rule.
« on: June 27, 2008, 03:58:30 PM »
Hello Organic Chemists. 

I am studying the dehydration of alcohols and have stumbled upon this very unique rule.... Zaitsev rule.

Unfortunately I am at a complete loss of understanding. 

Can anyone reference a website that clearly and 'simply' explains it? 

All my textbook says is:
Eliminations that are regioselective in the direction that yields the alkene with the most highly substitued double bond are said to obey the Zaitsev rule. 

It then proceeds to give the example:

(CH3)2CCH(CH3)2       ------>          2,3 dimethyl 1 butene              2,3 dimethyl 2 butene
          l                                            (minor product)                      (major product)
          OH
2,3, Dimethyl2-butanol

Can anyone give me direction as what a minor product and major product is....


Eeek!  I am lost...

p.s. is there an organic chemistry book on Zaitsev rule for dummies?  he he he....

going to drown my confusion in a movie and a large bag of popcorn...

THANK YOU!!!

New to organic chemistry

Offline Ak

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Re: Assistance with Zaitsev rule.
« Reply #1 on: June 27, 2008, 05:04:48 PM »
refering to the example given by your book...

in an elimination reaction 2 products can form, because the hydrogen can come off of Carbon 1 or Carbon 3 (OH is on carbon 2 and it comes off no matter what)

zaitsev's rule tells us that in an elimination reaction, the alkene that has more substitutes on the double bond will form more often then the one with less as it is more stable...hence the major product is the more stable product as it is produced more often

Offline bluenote

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Re: Assistance with Zaitsev rule.
« Reply #2 on: June 27, 2008, 08:43:02 PM »
As for good 'dummy' style books try Organic Chemistry as a Second Language.  It opened my eyes when I was an undergrad.

Offline NewtoAtoms

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Re: Assistance with Zaitsev rule.
« Reply #3 on: June 27, 2008, 10:00:01 PM »
Thank you so much Ak for the wonderful diagram, I deeply appreciate the time you took to explain it to me. I will just work on a bunch of examples, now that I have a base.

Thank you bluenote for the suggestion on the book.  As I type, I have just finished ordering it!!!

Have a great weekend everyone!

New to Organic Chemistry (and a little frightened!)

Offline azmanam

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Re: Assistance with Zaitsev rule.
« Reply #4 on: June 28, 2008, 07:08:03 AM »
The beginning of this website might be helpful, too

http://www.cem.msu.edu/~reusch/VirtTxtJml/alhalrx3.htm
Knowing why you got a question wrong is better than knowing that you got a question right.

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