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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.
(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)
___________________________ 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
OH
HO
Cl Cl
3 A. B. C. D. E.
HO
1, 4 2, 3 1, 2, 3 1, 3, 4 All
___________________________ 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.
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
___________________________ 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.
___________________________ 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
___________________________ 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
___________________________ 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
Reaction Coordinate
___________________________ 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.
___________________________ 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
____________________
___________________________ 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]
___________________________ 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.
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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 ___________________ ___________________ ___________________ ___________________
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