Exam 2 study Guide

1. When HBr is used to halogenate and alkene, it is possible you could get either Markovnikov
addition or anti-Markovnikov addition.

Explain why by showing likely mechanism of both reactions. Label which is

Markovnikov and which is anti-Markovnikov.
2. Write major product

Br2
CCl 4

3. Write major product

H2SO 4 , H2O
heat

4. Write reagents

1.
2.

OH

5.

Write reactants
1. O3
2. DMS

6. Write major product

1. MCPBA
2. HBr

draw one product with correct absolute

sterochemistry

7. Write major product

1. BH3
2. NaOH, H2O2

8.

Write major product

Cl2
CH2Cl2

draw one product with correct absolute

sterochemistry

9.

Write major product

O3

DMS

10. Write major product

Cl2, H2O

11. Write reagents

HO

12. Write major product

13. What are reagents

HO

14. Write major product

1) OsO4
2) NaHSO3, H2O

indicate sterochemistry of product

15. Order from strongest to weakest nucleophile. Explain. (8)

H2S
H2O
CH3CH2COOH
I
II
III

HS
IV

16. Determine the major product of the reaction and show the mechanism with proper electron
pushing for each step. (15)

17. Determine the major substitution product and elimination product of the reaction and show
the mechanism with proper electron pushing for each step. (15)

18. Write major product

OH

H2SO 4
high heat
180 C

19. Write major product

Cl

CH3CH2OH/CH3CH2OK

20. Write major product

CH3OH
Br

Expected minor product

21. Order from strongest to weakest nucleophile

a.

b.

c.

22. Draw the mechanism of the following reaction. Would this be the major product? Explain.
(10)
Cl

H2O

Label Mechanism

23. Draw the mechanism of the reaction. Explain why the major product violates Zaitsevs rule.
(10)
Cl
NaOEt/EtOH

Label Mechanism

24. Write major product

NaOCH3 / HOCH3

Cl

25. Write major product

Br

NaSH
DMSO

26. Write major product

OH

H2SO 4 , heat

27. Use the following compound to answer the following questions.

a. Draw the compound in a bond line structure.be sure to indicate stereochemistry

and label carbons 1-3 on your compound. (6)
b. Draw enantiomer of the structure in Fischer projection. (4)
c. Draw a diastereomer of the structure in Fischer projection.(4)
d. Draw geometric isomer of the structure in Fischer projection.(4)
e. Are any stereoisomers of the compound a meso compound? If so draw at one in
Fischer projection. (4)
28.
Draw: (1Z,3Z)-1-fluoropenta-1,3-diene
29. Name

Solutions

1.

2.

3.

4.
a. 1) BH3 2) H2O2, NaOH
5.

6.

7.

8.

9.

10.

11.
H2SO4, H2O or 1) Hg(OAc)2, H2O, H2SO4 2) NaBH4
12.

13. Hg(AcO)2, 2. NaBH4

14.

and enantiomer
15.
HS-> H2S>H2O>CH3CH2COOH
HS->H2S charged nucleophiles are better nucleophiles
H2S>H2O more polarizable are better nucleophiles (farther down periodic table)
H2O> CH3CH2COOH better bases are better nucleophiles

16.

17.

18.
19.

20.

and

21.
a. PH2- > HS- > Cl- increasing basicity
b. III > II > I increasing basicity
c. I > II > III less substitution, more free nucleophile
22.
The reaction is an E1 mechanism

The major product is a SN1 product

23. E2 elimination occurs through the only anti-periplanar H. Zaitsev product not possible

24.

25.

26.

27.

a.

b.

c.

d.

(many possibilities, must have C5H8O6 formula)

e. yes.
28.

29. (1R,3S) dichlorcylohex-4-ene