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13 Questions on Stereoisomers in Organic Chemistry I - Exam | CHM 2311, Exams of Organic Chemistry

Saint Joseph's University (SJU)Organic Chemistry

Prof. Mark Forman

Material Type: Exam; Professor: Forman; Class: Organic Chemistry I; Subject: Chemistry; University: Saint Joseph's University; Term: Fall 1997;

Typology: Exams

Pre 2010

Uploaded on 08/16/2009

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CHEMISTRY 2311-EXAMINATION III

NOVEMBER 21, 1997

DR. MARK A. FORMAN

NAME:

QUESTION

POINTS

SCORE

1 3 _______

2 6 _______

3 5 _______

4 15 _______

5 4 _______

6 4 _______

7 12 _______

8 12 _______

9 12 _______

10 9 _______

11 6 _______

12 6 _______

13 6 _______

TOTAL _______

Partial preview of the text

Download 13 Questions on Stereoisomers in Organic Chemistry I - Exam | CHM 2311 and more Exams Organic Chemistry in PDF only on Docsity!

CHEMISTRY 2311-EXAMINATION III

NOVEMBER 21, 1997

DR. MARK A. FORMAN

NAME:

QUESTION POINTS SCORE

1 3 _______

2 6 _______

3 5 _______

4 15 _______

5 4 _______

6 4 _______

7 12 _______

8 12 _______

9 12 _______

10 9 _______

11 6 _______

12 6 _______

13 6 _______

TOTAL _______

1. Assign an (R) or (S) configuration to the stereocenter in norepinephrine (3 points).

HO

C

OH

CH 2 NH 2

H

__________

2. Answer the following questions about tartaric acid.

COOH

H OH

COOH

a.) What is (R)/(S) designation of the indicated stereocenter? (3 points)

b.) Is this stereoisomer of tartaric acid optically active? Why or why not? (3 points)

3. a.) Place an asterisk at all stereogenic centers in guaiol (3 points).

H 3 C

H 3 C C

CH 3

H 3 C OH

b.) How many stereoisomers are possible for guaiol? Show how you arrived at this conclusion (2 points).

4. Identify the relationship between the following pairs of molecules by describing them as enantiomers,

diastereomers, constitutional isomers, or two molecules of the same compound. (15 points)

a.) b.) c.)

COOH

HO CH 3

H

HOOC CH 3

OH

C

CH 3

ClBr (^) H

C

Br CH (^3) H Cl

CH 3

H H

Cl Cl CH 3

CH 3

H Cl Cl H CH 3

_________ _ ____________

d.) e.)

CH 3 CH 2

C

H

CH 3

H

CH 3 CH 2 CH 3

CH 3 CH 3

__

5. Provide an IUPAC name for the following molecule (4 points).

C

CH 2 CH 2 CH 2 CH 3

HH 3 C^ Br

____________________________

6. What is a Grignard reagent? Give an example (4 points).

10. Draw all resonance structures for each of the following (9 points).

a.)

b.)

11. Consider the following reaction.

CH 3 CH 2 CH 2 I

NaOH dimethylsulfoxide (DMSO)

CH 3 CH 2 CH 2 OH

a.) What affect would you expect on the rate of the reaction if the concentration of sodium hydroxide is

doubled? Explain (3 points).

b.) What affect would you expect on the rate of the reaction if the solvent was changed from DMSO

(dimethylsulfoxide) to water? Explain (3 points).

12. Consider the following reaction.

CH 3

Br C CH 3 CH 3

13 Questions on Stereoisomers in Organic Chemistry I - Exam | CHM 2311, Exams of Organic Chemistry

Related documents

Partial preview of the text

Download 13 Questions on Stereoisomers in Organic Chemistry I - Exam | CHM 2311 and more Exams Organic Chemistry in PDF only on Docsity!

CHEMISTRY 2311-EXAMINATION III

NOVEMBER 21, 1997

DR. MARK A. FORMAN

NAME:

QUESTION POINTS SCORE

1 3 _______

2 6 _______

3 5 _______

4 15 _______

5 4 _______

6 4 _______

7 12 _______

8 12 _______

9 12 _______

10 9 _______

11 6 _______

12 6 _______

13 6 _______

TOTAL _______

1. Assign an (R) or (S) configuration to the stereocenter in norepinephrine (3 points).

HO

HO

C

OH

CH 2 NH 2

H

__________

2. Answer the following questions about tartaric acid.

COOH

H OH

H OH

COOH

a.) What is (R)/(S) designation of the indicated stereocenter? (3 points)

b.) Is this stereoisomer of tartaric acid optically active? Why or why not? (3 points)

3. a.) Place an asterisk at all stereogenic centers in guaiol (3 points).

H 3 C

H 3 C C

CH 3

H 3 C OH

b.) How many stereoisomers are possible for guaiol? Show how you arrived at this conclusion (2 points).

4. Identify the relationship between the following pairs of molecules by describing them as enantiomers,

diastereomers, constitutional isomers, or two molecules of the same compound. (15 points)

a.) b.) c.)

COOH

HO CH 3

H

H

HOOC CH 3

OH

C

CH 3

C

CH 3

H H

CH 3

___________________ ___________________ ____________________

d.) e.)

CH 3 CH 2

C

H

CH 3

H

CH 3 CH 2 CH 3

CH 3 CH 3

CH 3 CH 3

________________________ ______________________

5. Provide an IUPAC name for the following molecule (4 points).

C

CH 2 CH 2 CH 2 CH 3

____________________________

6. What is a Grignard reagent? Give an example (4 points).

10. Draw all resonance structures for each of the following (9 points).

a.)

b.)

11. Consider the following reaction.

CH 3 CH 2 CH 2 I

_________ _ ____________

__