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Practice Exam 2 - Organic Chemistry - Fall 1999 | CHEM 345, Exams of Organic Chemistry

University of Wisconsin (UW) - MilwaukeeOrganic Chemistry

Material Type: Exam; Class: Organic Chemistry; Subject: Chemistry; University: University of Wisconsin - Milwaukee; Term: Fall 1999;

Typology: Exams

Pre 2010

Uploaded on 09/02/2009

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Last Name _____________________________ First Name _______________________________
Please Print. Please put your name on the back of the test also.
EXAM 2 ORGANIC CHEMISTRY 345
October 18, 1999 Schwabacher
Quiz scores so far
page 2. (20 points) Q4
page 3. (30 points) Q5
page 4. (30 points)
page 5. (20 points)
page 6. (20 points)
TOTAL (120 points)
pf3
pf4
pf5

Partial preview of the text

Download Practice Exam 2 - Organic Chemistry - Fall 1999 | CHEM 345 and more Exams Organic Chemistry in PDF only on Docsity!

Last Name _____________________________ First Name _______________________________

Please Print. Please put your name on the back of the test also.

EXAM 2 ORGANIC CHEMISTRY 345

October 18, 1999 Schwabacher

Quiz scores so far

page 2. (20 points) Q

page 3. (30 points) Q

page 4. (30 points)

page 5. (20 points)

page 6. (20 points)

TOTAL (120 points)

O

H

NO 2

O

H

O

I. (15 points) Nomenclature: Provide a name for the given structure, or a structure for the

given name. Don't forget stereochemistry!

A)

B)

C)

D) 2-methoxycyclohexanecarbaldehyde

E) (S)-2-fluoro-2-phenylacetic acid

II. (5 pts) According to its manufacturer, "Delrin® … offers an excellent balance of desirable

properties that bridge the gap between metals and ordinary plastics. … High tensile

strength, impact resistance, and stiffness." Delrin has the polymeric structure shown.

Why should you avoid contact of Delrin with strong aqueous acid? What chemical reaction

would occur?

R O O O O O O (^) nO R

IV. (30 points) Provide products, showing stereochemistry for A.

A.

B.

C.

D.

E.

F.

O

O

O

O

CH 3

H 3 C

MgI 1) CO 2

  1. HCl

O

HO OH

cat. HCl

(-H 2 O)

O

H

H C N

cat. NaCN

Ph 3 P H

O

(Ph = phenyl)

O

H 2 N OH

Credit is given for each intermediate, so don't leave any steps out!

V. A. (10 points) Provide a mechanism for this acid-catalyzed reaction, showing all

intermediates, resonance forms, and all steps including proton transfers. Make sure

your mechanism shows the acid and the base for the proton transfer steps.

B. (10 pts.) Write a mechanism for this irreversible reaction, showing all intermediates,

and using curly arrows to indicate electron pair motion.

(Note that R-Li behaves like R-MgBr, but R-Li is quicker to write.)

O O

+ H 2 O

cat. HCl H 2 O solvent O^ OH

HO

O CH^3

O (^) LiCH

  • 2 (^3) CH 3

H 3 C (^) OLi (^) + LiOCH 3