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HW1 OC2 Solution

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28 views8 pages

HW1 OC2 Solution

Uploaded by

ngocthanh2821
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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1.

Answer:

a. 2-methyl-1,4-butanediol
b. 3-ethyl-2-hexanol
c. cis-1,3-cyclobutanediol
d. cis-2-methyl-4-cyclohepten-1-ol
e. cis-3-phenylcyclopentanol
f. 3-bromo-4-hydroxy-benzonitrile or 2-bromo-4-cyanophenol

2.

Answer:
3.

Answer:
4. Predict the major products (including stereochemistry) when
cis-3-methylcyclohexanol reacts with the following reagents.
a. PBr3
b. SOCl2
c. Lucas reagent
d. concentrated HBr
e. TsCl/pyridine, then NaBr

Answer:

5.

Answer: In each case one of the reagents might take a proton from the other. In
example (a), would the phenolate anion remove a proton from acetic acid? The
answer is yes because acetic acid is a much stronger acid than phenol The difference
is five pH units so the equilibrium constant would be about 105 and the equilibrium
would lie far across to the right.
6.

Answer: Electron-withdrawing effects make phenols more acidic and


electrondonating effects make them less acidic. Phenol itself (the fourth example)
has a pKa of 10. The only compound less acidic than phenol must be the third with
three weakly electron-donating methyl groups. One chlorine atom has an inductive
electron-withdrawing effect so the last compound has pKa 9. The remaining two
have the powerful electron-withdrawing nitro group. So the first compound, with two
nitro groups, must have pKa of 4 (making it as strong an acid as acetic acid) and the
second, with one nitro group, must have pKa of 7.

7. Identify the reagents you would use to accomplish each of the following
transformations.

Answer:
8. Identify all the reagents you would use to achieve the below product.

Answer: This type of transformation can be achieved via a Grignard reaction. However,
the starting material has an OH group, which is incompatible with a Grignard reaction. To
resolve this issue, we must first protect the OH group and then perform the desired Grignard
reaction. Deprotection then gives the desired product, as shown.

9. Give products and mechanisms for the following reactions.

Answer: In the first example, the ethyl Grignard reagent acts as a base to remove a
proton from the alkyne.
For the second example, it’s about making the organometallic reagent and adding it
to the carbonyl group. Cyclobutanone is more electrophilic than many other ketones
because of the strain of a carbonyl group in a four-membered ring.

The third example raises the question of which halogen is replaced. In fact, bromine
is more easily replaced than chlorine. Iodine is more easily replaced than either, and
fluorine usually does not react.

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