Name:___________________________ Student ID# ___________________________

CH 232/530 Exam II Chapters 16, 17, 18 (Mar. 1, 2005)

• You have 105 minutes to complete the exam.

1. (4 pts) When 1,2-epoxypropane is treated with sodium ethoxide in ethanol, 1-ethoxy-2-propanol is the
major product while only a trace amount of 2-ethoxy-1-propanol is produced. Use a complete electron
pushing mechanism to explain the major product formation.
 Score:_______/100

Combined Avg. for Exam II:_________%

2. (10 pts) Draw the structures for each of the compounds indicated below:

DIBAL DME

Benzyl Alcohol Ethylene Glycol 18-Crown-6

3. (4 pts) When 4-chloro-1-butanol is treated with sodium hydride, tetrahydrofuran is produced. Provide
a mechanism.

O
NaH, Et 2 O + NaCl
ClCH2 CH2 CH2 CH2 OH
 4. (10 pts) Isobutylbenzene
Isobutylbenzene is the starting material for the industrial synthesis of the NSAID, ibuprofen.

A. Attempts to prepare isobutylbenzene by direct Friedel-Crafts alkylation of benzene result in tert-

butylbenzene as the major product. Write the complete stepwise mechanism for this reaction, showing all
electron flow with arrows and showing all intermediate structures.

B. Propose a synthesis for isobutylbenzene which avoids the problems of direct Friedel-Crafts alkylation.
5. (14 pts) Major Organic Products
Give the major organic product(s) of each of the following reactions. Indicate proper stereochemistry
where appropriate.
6. (6 pts) Write the mechanism of the hydrolysis of cis-5,6-epoxydecane by reaction with aqueous acid
(hydronium). What is the stereochemistry of the product(s) assuming backside attack occurs? Be sure to
show all expected products.
7. (8 pts) Phenols
Refer to the data below to answer the following questions.

A. The weakest acid in the table is:

B. Which of the acids in the Table has the weakest conjugate base?
C. How do you account for the difference in acidity between meta and para-nitrophenol? Use
comparative resonance structures to explain.
8. (6 pts) Grignard Reagents
A highly useful and general method for the synthesis of alcohols is the addition of Grignard reagents to
carbonyl compounds. Show what Grignard reagent and what carbonyl compound you would start with to
prepare each alcohol below. There may be multiple answers for each question, but just give one viable
solution.

9. (18 pts) Starting Materials

Propose structure(s) for the starting material(s), reagent(s), or major organic product(s) of the following
reactions or sequences of reactions. Show all relevant stereochemistry.
 O O
OH TBSO

1. LiAlH4 , Et 2O
2. H2O
3. Bu 4N + F-

O O

EtO EtO

OH Cl

DIBAL, -78 oC
10. (10 pts ) At what position(s) on the following molecules would you expect electrophilic aromatic
substitution to occur? Indicate all possible positions by clearly circling the appropriate atom(s). Assume
the electrophile is the limiting reagent:

Example

CN CN

H
N

Br

O
11. (10 pts) Propose a synthesis of Dimestrol starting from p-methoxypropiophenone as the only source
of carbon.