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Topic: For which reaction is the equilibrium constant the greatest?  (Read 5004 times)

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Offline NewtoAtoms

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For which reaction is the equilibrium constant the greatest?
« on: February 22, 2009, 07:47:33 PM »
For which reaction is the equilibrium constant the greatest?

a. 1
b. 2
c. 3
d. 4

I have done the leg work I just would appreciate some guidance.
I know that equilibrium constant are greater of aldehydes than for ketones
However these are all aldehydes therefore I am forced to examine the substituents.

                       OH
                       l
1. CH3CH2CH2 - C - H                                       C (OH, H, CN, CH2CH2CH3)
                       l
                       CN

                       OH
                       l
2.  CH3CH2CF2- C - H                                        C (OH, H, CN, CH3CH2CF2)
                       l
                       CN

               OH
               l
3. CH3CH2CCH3                                                 C (OH, CH3, CN, CH2CH3)
               l
               CN

                OH
                l
4.  CH3CF2CCH3                                                 C (OH, CH3, CN, CH3,CF2)
                l
                CN

Looking at the above substituents that are attached to the C, I would conclude that 1 has the greatest equilibrium constant because according to the steric affects, it is less crowded in comparison with the others.

Can anyone tell me if my reasoning is correct?

Thank you for your help and time.
Have a great day.

New to Atoms.

Offline nj_bartel

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Re: For which reaction is the equilibrium constant the greatest?
« Reply #1 on: February 22, 2009, 10:19:11 PM »
Those aren't all aldehydes (3 is actually the least reactive of any of them).

Offline NewtoAtoms

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Re: For which reaction is the equilibrium constant the greatest?
« Reply #2 on: February 23, 2009, 06:57:34 AM »
Pardon me, I apologize for my mistake.
Yes 1 and 2 are aldehydes and 3 and 4 are ketones. 
According to my notes, aldehydes have a greater equilibrium constant than ketones, therefore either 1 or 2 would be have the greatest equilibrium constant. Because they are both aldehydes, I should then compare the substituents correct? In comparison #2 has 2 F's attached therefore the crowding is more and the equilibrium constant is lower than that of 1.  Is this correct?  Is my reasoning correct or am I totally missing something.

Thank you for your time

New to atoms

Offline sjb

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Re: For which reaction is the equilibrium constant the greatest?
« Reply #3 on: February 23, 2009, 07:41:28 AM »
Actually, the size difference between a fluorine and a hydrogen in these circumstances isn't that much. I'd perhaps look into electronics as well as sterics.

S

Offline McCoy

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Re: For which reaction is the equilibrium constant the greatest?
« Reply #4 on: February 23, 2009, 09:56:25 AM »
I can choose #2 because there are 2 electron rich species on the alpha carbon.

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