Download Alcohols/Wade: Reactions

Alcohols/Reactions
Name: ______________________
1. Predict the major products of the following reactions.
a) (R) – 2- butanol + TsCl in pyridine
b) (S) – 2-butyl tosylate + NaBr
c) Cyclooctanol + CrO3/H2SO4
d) Cyclopentylmethanol + CrO3.pyridine.HCl
e) Cyclopentylmethanol + Na2Cr2O7/H2SO4
f) Cyclopentanol + HCl
g) Cyclopentanol + H2SO4/heat
h) Product from above + OsO4/H2O2 followed by HIO4
i) Sodium methoxide + t-butyl iodide
j) Sodium ethoxide + 1-bromobutane
Dr. Gupta/Wade/Alcohols-Reactions/Page 1 of 7
2. Predict the major products of dehydration by acid catalysis.
a) 1-hexanol
b) 2-hexanol
c) 3-pentanol
d) 1-methylcyclopentanol
e) Cyclopentylmethanol
f) 2-methylcyclopentanol
3. When 1-cyclohexylethanol is treated with aqueous HBr, the major product is 1-bromo-1ethylcyclohexane. Give a mechanism for the reaction.
How would you convert 1-cyclohexylethanol to (1-bromoethyl)-cyclohexane in a good yield?
Dr. Gupta/Wade/Alcohols-Reactions/Page 2 of 7
4. Show how you will make each of the following compounds from an alcohol of your choice.
a) .
b) .
c) .
d) .
e) .
f) .
g) .
h) .
i) .
Dr. Gupta/Wade/Alcohols-Reactions/Page 3 of 7
5. Predict the major products (including stereochemistry) when (cis)-3-methylcyclohexanol
reacts with the following reagents.
PBr3
SOCl2
Conc HBr
(cis)-3-methylcyclohexanol
TsCl/pyridine, then NaBr
6. What simple chemical test can you use to distinguish between the following pairs of
compounds? Write the test and the observation.
a) 1-butanol and 2-butanol
b) 2-butanol and 2-methyl-2-butanol
c) Cyclohexanol and cyclohexene
7. How will you synthesize the following compound from compounds of 6 carbons or less?
Dr. Gupta/Wade/Alcohols-Reactions/Page 4 of 7
8. Show how you would carry out the following conversions.
a) .
b) .
c) .
d) .
9. Predict the esterification products of the following acid/alcohol pairs.
a) CH3CH2CH2COOH + CH3OH
b) .
c) .
d) 2CH3CH2OH + H3PO4
e) CH3OH + HNO3
Dr. Gupta/Wade/Alcohols-Reactions/Page 5 of 7
10. Compound A is an optically active alcohol. Treatment with chromic acid converts A to a
ketone B. In a separate reaction A is treated with PBr3, converting A to C. Compound D is
purified and reacted with magnesium and ether. Compound B is added to the resulting
solution of the Grignard reagent. After hydrolysis, this solution is found to have 3,4dimethyl-3-hexanol. Propose the structures for A, B and C.
PBr3
A
H3O+
Mg, ether
C
Grignard Reagent
Na2Cr2O7, H2SO4
D
3,4-dimethyl-3-hexanol
B
11. Give the structures of the following products V through Z.
PBr3
Cyclopentanol
Mg, ether
W
O
||
CH3C-Cl
i) V
X
Y
Z
ii) H3O+
Na2Cr2O7, H2SO4
V
12. Show how you would synthesize the following compounds using alcohols of 4 or less
carbons and any other reagents of your choice.
a) .
b) .
Dr. Gupta/Wade/Alcohols-Reactions/Page 6 of 7
c) .
d) .
e) .
f) .
13. Determine the structures A through G in the following scheme.
Dr. Gupta/Wade/Alcohols-Reactions/Page 7 of 7