Practice Sets - Minnesota State University Moorhead

1

Practice Sets

Organic Chemistry II Table of Contents

? Online Organic Chemistry II, Chem 360,

? Dr. Craig P. Jasperse, Minnesota State University Moorhead

? For full class website, see

? Fall/spring: ? Summer: ? Face:

Test Test 1 PS#1: Arrow-Pushing/Mechanisms Practice Set Test 1 PS#2: Acid Base Practice Set Test 1 PS#3: Alcohol-related Mechanisms Problems Test 1 PS#4: Alcohol-Related Retrosynthesis Problems

Page 3 7 11 15

Test 2 PS#1: Jasperse NMR Problems

17

(this will only show the first ten or 42. It will have link to the full 42-

problem practice set, which are also included in the class notes.

Test 3 PS1: Mechanism Practice (Many)

27

Test 3 PS2: Retrosynthesis + Synthesis Design Practice

35

Test 4 PS1: Acid-Base Practice 1 (Easy, basics)

39

Test 4 PS2: Acid-Base Practice 2 (Harder, more test representative) 43

Test 4 PS3: Mechanisms, Retrosynthesis + Synthesis

45

2

Test 1 PS#1: Arrow-Pushing/Mechanisms Practice Set

3

1

Chem 360

Name:

Jasperse

Quiz (mechanisms)

Due:

Arrow-Pushing Practice, Page 1:

? Draw arrows for each of the steps in the following reactions. ? I won't require this on tests, but you may find it useful to include all lone-pairs on atoms that

react.

? I won't require this on tests, but you may find it useful to draw in all hydrogens on atoms that react. (It is not useful to draw in all H's on atoms that don't react.)

? Remember that arrows track the movement of electrons, so an arrow should go from the source of electrons and point directly to the atom that accepts them.

1. (Old Test)

O H

+ H-Br

H O

H2O

H

Br

H O

OH2 H

Br

2. SN2

Br + NaI

I + NaBr

3. E2

Br

+ NaOH

H

H

H

Br 4. SN1

+ HOH + NaBr

H

H

H

H

O

OH

H2O

+ Br-

+ H

Br 5. E1

H2O

H

H

H

+ Br

+ H3O

H

H

Test 1 PS#1: Arrow-Pushing/Mechanisms Practice Set

Page 2: Draw the arrow(s) for each of these steps.

OH H+

1.

OH2

2.

+

H H2O

3.

HH

OH2 + H2O

+ H3O+

Br

4. Ph

Br

_ OH

5. Ph

+ Ph

_ + Br

OH _

Ph

+ Br

6. Ph

D-Br

_ Ph + D + Br

7. Ph +

D

+

_ Br

Br D

Ph

O

CH3

H

8.

O

_ OCH3

9.

O

H

H CH3

_ O

OCH3

OH H

CH3

10. Ph

Br-Cl

Ph + Br+ Cl _

Cl Br

Ph

Br H NEt3

11. H H

+

_

+ H NEt3 + Br

4 2

Test 1 PS#1: Arrow-Pushing/Mechanisms Practice Set

5

3 For each of the following reactions, write whether the mechanism would be radical, cationic, or anionic?

HNO3

NO2

1.

Br NaOH

OH

2. O2N

O2N

O CH3OH, H+

H3CO OCH3

3.

H

H

Br Br2, peroxides

4.

O Br2, NaOH

5.

O Br

O H2O, H+

OH

OH

6.

peroxides

7.

etc

etc

H3CO OCH3 H2O, H+ O

8.

O LiCH3

OLi

9.

CH3

 ................
................

In order to avoid copyright disputes, this page is only a partial summary.

Google Online Preview   Download