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Seat # _____

Name: ______________________________ Signature: ___________________________ Lecture Section: ____________________

ORGANIC CHEMISTRY
CHEMISTRY 307 Exam II November 4, 2007

The exam has 6 multiple choice questions and 8 written problems. Please answer the multiple choice questions on the Opscan form. Please put your name in the designated place on every page of the exam.
ON THE OpScan FORM: (do not separate)
I. II. ____________ ____________ ____________ ____________ ____________ ____________ ____________ ____________ ____________

(Use a Number 2 Pencil) (1) SIGN your name across the TOP of the form.

III. IV. V. VI. VII. VIII.

(2) code only the following information: [blacken circles] (a) Your Name . . . LAST NAME FIRST [blank space between last and first name] (b) Your RU ID NUMBER [Start under Box A and continue through to Box I] Your LECTURE SECTION NUMBER (Boxes K & L) Your EXAM FORM NUMBER

TOTAL:

(c)

C Si

N P

O S

F Cl Br I

(d)

(Box P)

Your EXAM FORM is: 1

___________________________ PRINT NAME 1. What factors will increase the rate of the SN2 reaction shown? Nu
LG

solvent

+
Nu

LG

(LG is the leaving group and Nu is the nucleophile) 1. Concentration of substrate 2. polar protic solvent 3. larger nucleophile 4. concentration of nucleophile 5. more substitution at adjacent carbon 6. less basic leaving group A. B. C. D. E. 2. 1, 2, 4 All of the above 1, 2, 4, 6 1, 3, 6 1, 4, 6

Which of the following are achiral?


OH H Cl H3C H3C CH3

OH

HO

Cl Cl

3 A. B. C. D. E.

HO

1, 4 2, 3 1, 2, 3 1, 3, 4 All

307 EXAM II V1 FALL 2007

___________________________ PRINT NAME 3. Of the following compounds, which is (are) least likely to undergo an E2 reaction?
H H H3C Br H CH3 Br Br

2
Br Br

4 A. B. C. D. E. 1 and 4 4 and 5 1 and 2 2 and 3 3 and 5

4.

With a secondary substrate, which of the following factors will be most likely to cause a nucleophilic substitution to follow the SN1 rather than the SN2 pathway? A. B. C. D. E. weaker nucleophile stronger base increased concentration of nucleophile lower temperature use of a polar aprotic solvent

307 EXAM II V1 FALL 2007

___________________________ PRINT NAME 5. Which of the following is the best polar aprotic solvent for an SN2 reaction? A. B.
O OH

C.
O

Cl

D.

OH

E. H

CH3

CH3

6.

What is the color of your exam? A. B. C. D. White Yellow Pink Blue

307 EXAM II V1 FALL 2007

___________________________ PRINT NAME I. (12 points) With each of the following compounds, fill in the template provided with the type of structure requested. Write in the correct stereochemical designation of each member of each pair of compounds.
H3C CH3 H

A.

H2C H

NH2

Same compound

B.
Cl CH3 F H Diastereomer

CH3

C.

Cl Cl Cl CH3 Enantiomer

H3C

D.
H H3C H Meso compound

307 EXAM II V1 FALL 2007

___________________________ PRINT NAME II. (6 points) The S enantiomer of a chiral compound has a specific rotation of +20 . A 1.0 g sample of the pure R enantiomer is contaminated with 1.5 g of the racemic form of the compound. What is the % enantiomeric excess of the contaminated sample, the % of each enantiomer and the optical rotation of the sample? Show calculations.
o

% Enantiomeric excess

%R

%S

Optical rotation

307 EXAM II V1 FALL 2007

___________________________ PRINT NAME III. (12 points) Write out the complete mechanisms for the reactions given. Be sure to include all nonbonding electrons and charges, and to indicate all electron movement with appropriate curved arrows. On the axes provided, sketch the reaction coordinate diagram for the reactions given. On each diagram indicate the structure of any intermediates and/or transition states. Assume each overall reaction is spontaneous. A. ethyl bromide + OH
-

ethanol + Br

Reaction Coordinate

B. t-butyl bromide + CH3OH

t-butyl methyl ether + Br- + CH3OH2+

Reaction Coordinate

307 EXAM II V1 FALL 2007

___________________________ PRINT NAME IV. (8 points) a. Draw the structure of all the organic products of each of these reactions, showing stereochemistry. Use the same form of representation as in the starting materials.

A.

+ CH3OH

B.
Br H

HS

DMSO

b. Identify the specific type of reaction in A and in B and explain in ten words or less [only your first ten words will be considered] for each why it has the stereochemical outcome shown in your answer to part a.

307 EXAM II V1 FALL 2007

___________________________ PRINT NAME V. (10 points) Using the templates given, fill in the structures of the indicated stereoisomers of the compound shown.
NH2

Cl

5-chloro-2-hexanamine

2 2R, 5S

5 2

2R, 5R

2 2S, 5S

5 2 2S, 5R

Using the stereochemical designations (R and S), list the pairs of enantiomers and the pairs of diastereomers. Enantiomers ____________________ ____________________

Diastereomers

____________________

____________________ ____________________ ____________________

307 EXAM II V1 FALL 2007

___________________________ PRINT NAME VI. (12 points) a. Draw the structures of the major organic products of the reactions shown.

H2O

Br O

DMF
Br

H3C S O

O O H

HS acetone

CH3OH
H3C CH3

b. What is the principal factor that causes a particular secondary substrate to undergo an E2 rather than SN2 reaction? [five words or less]

307 EXAM II V1 FALL 2007

___________________________ PRINT NAME VII. (8 points) a. Draw the structure of the major product of the following reaction indicating its stereochemistry..

CH3 O

Br

acetone

b. With the help of a Newman projection diagram of the substrate account for the stereochemistry of the product shown.

307 EXAM II V1 FALL 2007

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___________________________ PRINT NAME VIII. (12 points) List four principal factors (two words or less for each) affecting nucleophilicity and for each give a pair of substances whose difference in nucleophilicity results primarily from that factor. Indicate for each pair which is the stronger nucleophile. 1. ______________ _______________ stronger 2. ______________ _______________ stronger 3. ______________ _______________ stronger 4. ______________ _______________ stronger ___________________ ___________________ ___________________ ___________________

307 EXAM II V1 FALL 2007

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