Org Chem Practice Test - Check solutions?

Started by bmathew, October 11, 2010, 06:48:14 PM

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bmathew

Hi, I did a practice test for an upcoming organic chemistry midterm. There are no solutions posted so I was hoping you could check to see if my answer are correct, and if not give me an idea of what I did wrong:

1) http://img299.imageshack.us/i/orgt1.jpg/

2) http://img840.imageshack.us/i/orgt2.jpg/

3) Rank the following in order of acidity  (1=lowest, 7= highest): Ethanol, Acetic Acid, Water, Phenol, Ethyl Amine, Methane, Triflouroacetic acid

My answer:
1: Methane
2: Ethyl Amine (N is less electronegative than O, so a negative charge on N would be less stable than one on O and thus the conjugate base of N would be less stable than one for oxygen, meaning it is a weaker acid)
3: Water (I didn't really know where to put this one, but I think it's roughly neutral?)
4: Ethanol (Here there are 2 electron donating alkyl groups)
5: Acetic Acid (Here there is 1 electron donating alkyl group)
6: Phenol (Resonance stabilized)
7: triflouroacetic acid (1 electron withdrawing group with highly electronegative Flourines)

4)http://img832.imageshack.us/img832/5742/orgt3.jpg

5) Use Newman projections to illustrate why 2-flouroethanol has a greater dipole moment than 1,2-diflouroethane

Is this because in 1,2-diflouroethane, there will be no dipole in an anti conformation (it will cancel out), whereas in 2-flouroethanol, there will be a dipole in all conformations?


I would appreciate it if you could just check over my answers and point out any mistakes I might have made. Thank you very much.

uma

I can not see the pictures
Please attach the file with the message


uma

My answer:
1: Methane
2: Ethyl Amine (N is less electronegative than O, so a negative charge on N would be less stable than one on O and thus the conjugate base of N would be less stable than one for oxygen, meaning it is a weaker acid)
3: Water (I didn't really know where to put this one, but I think it's roughly neutral?)
4: Ethanol (Here there are 2 electron donating alkyl groups)
5: Acetic Acid (Here there is 1 electron donating alkyl group)
6: Phenol (Resonance stabilized)
7: triflouroacetic acid (1 electron withdrawing group with highly electronegative Flourines)

here order is okay except water and ethanol
Get the order of acidity of water and ethanol as indicated by their pKa of 15.7 and 16 respectively.
presence of electron donating group on OH will reduce the acidity of ethanol in compare to water.

uma

in image 1 - for first compound
there is no methoxy group
it is methyl on 5carbon and on 4th carbon is N-methylamino
now change the name accordingly

for the third with the newman projection you have only three carbons in the main chain
so it must be
2-methylpropanol
rest are okay


uma

Here is the answer for second image. Please see the attachment.

uma

for the third image
your first newman projection is wrong '
you have made 1-cyclopentyl-5-methylhexane
you need to put one more methyl group on the back carbon of newman projection
second one is right

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