ORG CHEM II
Problem Set Chapter 17
ANSWER KEY
1. Name the following compound using IUPAC nomenclature.
OH
CH3CHCH2CH2CHCH3
5-phenyl-2-hexanol
2. Compound A has the formula, C7H14OH. When it is reacted with POCl3 in
pyridine, it forms Compound B, C7H12. Compound B reacts with ozone,
followed by zinc in acetic acid, to form Compound C,
O
O
HCCH2CH2CH2CH2CCH3 . Draw the chemical structures for Compounds A &
B.
CH 3
CH 3
OH
O
POCl3
2) Zn, H+
A
O
1) O 3
B
H
CH 3
C
3. Over each arrow show the chemical reagents and conditions needed to
perform the following reactions. (Only one reaction is implied for each
example below.)
PCC, CH 2Cl 2
a. CH3CH2CH2CH2OH → CH3CH2CH2CHO
SOCl 2
b. CH3CH2CH2CH2OH → CH3CH2CH2CH2Cl
CrO 3, H 2SO4
c. CH3CH2CH2CH2OH → CH3CH2CH2CO2H
d. CH3CH2OH
NaH
→ CH3CH2O-Na+
4. Complete the following road map using any needed reagents, containing 4
or less carbons, and any needed conditions. Show the major product for
each reaction used.
OH
CH 3CH 2CH 2CH 2OH
OH
POCl3
CH 3CH 2CHCH3
Hg(OAc)2 NaBH 4
H2SO 4
H2O
CrO3
H2SO 4
OH
O
8. What reagent or series of reagents would you need to accomplish the
following conversions? A series of reactions should be numbered in sequence.
O
CH 2CH 3
POCl 3
1) CrO 3, H 2SO 4
2) CH 3CH 2 MgX
3) H3O +
CrO 3
H2SO 4
OH
1) POCl 3
2) O3
3) Zn, H+
PBr 3
Br
1) POCl 3
2) OsO 4
3) NaHSO 3
H
H
OH
OH
O
O
9. Show three different Grignard reactions which would result in the alcohol at
right.
CO 2CH 3
1) 2eq CH3 MgX
2) H3O +
C
O
H3C
O
C
CH 3
1) CH3 MgX
2) H3O +
1)
2) H3O +
CH 3
MgX
10. Show, over the arrows, the reagents and conditions needed for the
transformat
CH 2Cl
CO 2H
CO 2H
2eq LiAlH4
CHO
SOCl 2
CrO 3
CH 2OH
NaBH4
PCC
O
O
MgX
1)
H
C
CHO
H3C
H
S Cl
O
2) H3O
+
NaH
CH 2O- Na+
CH 2OTs
11. What reagents are needed for the following transformations? If more than
one reaction is necessary, show each set of reagents and conditions over a
separate arrow and show the major product for each reaction.
PCC
a. CH3CH2OH → CH3CHO
1) NaBH 4
2) H 3 O+
b. CH3CHO →
CH3CH2OH
SOCl 2
c. CH3CH2OH → CH3CH2Cl
NaH
d. CH3CH2OH
→ CH3CH2O-Na+
CrO3 , H 2 SO 4
e. CH3CH2OH →
CH3CO2H
f. CH3CH2OH → CH3CH2CO2H