STUDY GUIDE FINAL

1. How can you convert the alcohol A to B? Write down all the reaction and reagent
needed. You may need several steps.

2. What will the oxidation product of the following alcohol?

3. Write a reasonable mechanism for the following reaction.

4. Write down the reagents that you will need to perform the following two step reaction.

5. Write the product(s) or reactants of each reaction.

a.

b.

c.
 d.

6. Exercise 8.21 in your book (page 248) (11th Ed.)

The following steps can be used to convert anisole to ortho-t-butylanisole. Give the
reagent for each step. Explain why over-all result cannot be achieved in one step by a
Friedel-Crafts alkylation. (Hint: Section 4.10 and 4.11 may be helpful for the second part
of this question.)

7. Write the product(s) or reactants of each reaction.

e.

f.

g.

8. Synthesize following compounds using starting materials with maximum 6 carbon atoms.

a. b.
 c. d.

9. Using the given hints, find the structures of A and B.

10. Draw the most stable chair conformations for the following compounds.

Br
Cl

N
H
F

11. Draw the lowest and highest energy rotamers of the following compound for the
indicated bond.

Cl
Br

F
 12. Synthesize the following compounds starting from given starting materials.

OCH3 OCH3 O

Br Cl NO 2

13. Fill in the boxes for the following synthesis.

Br
NaNH 2 Pd/C, H 2
+
14. Fill the boxes with correct product.

HBr

H +, H 2O

1) BH 3

2) NaOH, H 2O2

1) O3

2)Zn, AcOH

15. Draw all possible resonance structures for the following compounds
 HO 3S
MeO N

NO 2

16. Give the major product that you would expect to be formed in each of the following
reactions. If you think there is no reaction write NR after the arrow. In each case give the
mechanism (SN1, SN2, E1 or E2) by which the product is formed. Also indicate the correct
stereochemistry when applicable. Both product and the mechanism should be correct to
get credit. No partial credit.

NaI t-BuOK
Acetone t-BuOH
NaSH
DMF

Br H NaOMe
MeOH,rt DMSO

O
t-BuOH
S heat
DMF NaN3
DMF

17. Show how would you achieve the following syntheses. More than one step is required.
You can use any reagent or reactant you want.
 O
Br
HO

Cl

Cl

18. Show how would you achieve the following syntheses.

HO

OH

OH

O
O O O
19. Complete the following reactions.
 OH
PDC (excess)

HO OH DMF

HO

PDC (excess)
OH DMF
OH

O
H 1) NaOH
O
+
H 2) H +, H 2O, heat
S

O O MeOH (excess)
H cat. H 2SO 4

O O 1)LiAlH 4 (excess)
H 2) H 2O

O
1) NaCN, DMF

2) H +, H 2O

O
NaBH 4, MeOH

20. Write a reasonable reaction mechanism for the following imine formation reaction?
 H 2N
O H +, N

CH 3 CH 3

21. Show how would you achieve the following synthesis.

HO

22. Show how would you achieve the following synthesis.