Organic Chemistry 2 Major

Mid-Term Exam 3

April 18, 2011

Instructions. Answer all questions on the answer sheets in the back of the exam with the letter, number, or drawing that corresponds to the best answer. All questions are 10 points each. At the end of the exam, turn in the answer sheets only. You may keep the exam. Important! Before you begin, put your name and ID number on all of the answer sheets. 1. Write the structures of the organometallic compounds (A and B) formed from the following reactions.
a) H3C CH3 Br + 2Li diethyl ether

b) H3C

CH3 Br

Mg

diethyl ether

2. Give the major organic product (A and B) of each of the following reactions.
O a) MgBr ND3 1) MgBr 2) H3O+ H

b)

3. Give the best reagent(s) for step 1 (A) and the major organic product for step 2 (B).
Reagent(s) OH H O NaBD4, H2O step 2

A
step 1

major organic product

4. Give the major organic product (A and B) of each of the following reactions.
nol etha H 4, m Na B

O H O OH

ss exce

1) ex c 2) H ess LiAlH O
2

4,

dieth y

l ethe r

5. Give the organometallic intermediate (A) and the major organic product (B) of the following reaction.
O 1) H 3C H CH3CH2MgBr diethyl ether

2) H3O+

Organic Chemistry 2 Major

Mid-Term Exam 3

April 18, 2011

6. Give the major organic product (A) including stereochemistry of the following reaction.
MgBr CH3 CH3 CH3 1) 2) H3O+ CH3

7. Give the organometallic intermediate (A) and the major organic product (B) including stereochemistry of the following reaction.
CH3 H O O S O

2 H3C

Li

1 CuI diethyl ether

H 3C

8. Predict the principle organic product (A and B) of each of the following reactions (14.24 b, f).
+ O CH3CH2Li 1) diethyl ether 2) H3O+

A
H3CO

LiCu(CH3)2

9. Give the intermediate (A) and the major organic product (B) including stereochemistry of the following reaction.
CH3 O OH HO SOCl2

A
(pyridine) N

10. Suggest reaction sequences and reagents suitable for carrying out the following conversion. Two synthetic operations are required in each case (15.30 c).
OH to OH OH (racemic)

Organic Chemistry 2 Major

Mid-Term Exam 3

April 18, 2011

11. Give the major organic product (A) of the following reaction.
OH (racemic) OH HIO4

12-13. Give the major organic product (A to D) of each step of the following reaction sequence.
1) B2H6, diglyme 2) H2O2, HO-

K2Cr2O7 H2SO4, H2O

CH3OH H2SO4, heat

excess CH3CH2CH2CH2MgBr

14. Give the major organic product (A) of the following reaction.
O O H3CO OCH3 1 equiv Br2 FeBr3

15. Give the major organic product (A) of the following reaction.
O OH O 1 equiv.Br2 acetic acid

16-17. Draw MAJOR resonance form(s) leading to MAJOR product(s) in the reactions of bromobenzene (1) and benzonitrile (2) with 1 equiv Cl2 using FeCl3 as catalyst. If more than one product is formed, draw ALL major resonance forms involved.
Br 1 equiv Cl2 FeCl3 1 2 CN 1 equiv Cl2 FeCl3

18. Starting from benzene, propose a synthesis (specify the reagent(s) required) for the following compound (1). If more than one step is required, draw the major organic product for each step. There is more than one possible answer to this question.
CH3 from Br 1 benzene

(a mixture of E/Z isomers)

Organic Chemistry 2 Major

Mid-Term Exam 3

April 18, 2011

19. Suggest a suitable series of reactions for carrying out each of the following synthetic transformations (12.47 d).
OCH3 O2N to OCH3 H3C OCH3 CH CH3 3 OCH3

20. Rank the following aromatic compounds by INCREASING reactivity toward electrophilic aromatic substitution reactions. Use inductive effects and/or resonance effects to explain the order. (q 2, quiz 7).
H N O CH3 a) b) H N CH3 N CH 3 CH3 c)

21 (bonus question quiz 8). Use retrosynthetic analysis to determine ONE possible route to the following tertiary alcohol. You can use benzene, anisole, organic molecules with no more than FOUR carbons, and inorganic reagents.
H 3C O OCH3 OH from

anisole

benzene

CH3