Synthesis Practice

Chapter 12

1. For the transformation shown, select the most appropriate reagent(s) to effect the change.

A)
B)
C)
D)
E)

1) OsO4; 2) NaHSO3, H2O

1) Hg(OAc)2, H2O; 2) NaBH4
1) RCO3H; 2) H3O+
1) BH3THF; 2) H2O2, NaOH
1) O3; 2) DMS

2. Selectthebestreagenttoconvert1-bromo-1-methylcyclohexane to 1-bromo-2methylcyclohexane.
A)
1) KOtBu; 2) HBr
B)
1) NaOEt; 2) HBr
C)
1) NaOEt; 2) HBr, ROOR
D)
1) KOtBu; 2) HBr, ROOR
E)
Br2, h
3. Which of the following sequences of reagents will move the alcohol functional group
from the tertiary position of 1-methyl-1-cyclohexanol to a secondary position?
A)
1) KOtBu; 2) Hg(OAc)2, H2O; 3) NaBH4
B)
1) TsCl, pyr; 2) KOtBu; 3) BH3-THF; 4) H2O2, NaOH
C)
1) H2SO4, heat; 2) BH3THF; 3) H2O2, NaOH
D)
1) TsCl, pyr; 2) NaOH; 3) BH3THF; 4) H2O2, NaOH
E)
C and D will both work
4. Reaction of compound A (molecular formula = C12H24) with ozone followed by reaction
with DMS produces only (CH3)3CCH2CHO. Which of the following could be compound
A?
A)
cis-2,3,7,8-tetramethyloct-4-ene
B)
trans-dodec-6-ene
C)
4,4-dimethylpent-1-ene
D)
cis-2,2,7,7-tetramethyloct-4-ene
E)
2,2-dimethyldec-4-ene

5. Which reagents will accomplish the following transformation?

A)
B)
C)
D)
E)

NaNH2
1) O3; 2) H2O
KMnO4
1) BH3THF; 2) H2O2, NaOH
H2SO4, H2O

6. Compound X has molecular formula C8H10. Reaction of Compound X with excess ozone,
followed by reaction with dimethyl sulfide and then washing with water produces only
the compounds shown below. Draw a possibility for Compound X that is consistent with
these results.

7. Propose an efficient synthesis of cyclopentanone from 1-methylcyclopentane:

8. The following sequence of reactions transforms acetylene into a compound with an

altered carbon skeleton (compound 1), and from that into a compound in which the
functional group has been changed (compound 2). Identify compounds 1 and 2:

9. Which of the following sequences efficiently converts 2-methylpropene and sodium

acetylide into 3-methylbutanal?

A)
B)
C)
D)
E)

1)
1)
1)
1)
1)

HBr; 2) NaCCH; 3) O3; 4) H2O

HBr; 2) NaCCH; 3) O3; 4) DMS
HBr, ROOR; 2) NaCCH; 3) O3; 4) H2O
HBr, ROOR; 2) NaCCH; 3) H2/Ni2B 4) O3; 5) DMS
NaCCH; 2) H2/Ni2B; 3) O3; 4) DMS

10. Propose a strategy to prepare the target as one of the major products:

11. Using retrosynthetic analysis, determine which compound(s) could lead to the
bromoalkene shown below in a single step:

12. Show that you understand the concept of retrosynthetic analysis by working backwards
two steps in the synthesis below. Identify possible combinations of A and B that could
lead to the alkyl halide (C).

13. Devise a method to complete the following synthesis.

14. Devise a synthesis to lengthen the legs of Ralph as requested below.

15. Propose a three-step synthetic sequence to accomplish the transformation below.

16. Propose a multi-step synthetic sequence to accomplish the transformation below.

17. Propose a multi-step synthetic sequence to accomplish the transformation below.

18. Propose a three-step synthetic sequence to accomplish the transformation below.