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Solved Multiple Choice Questions on Organic Chemistry II - Exam 2 | CHEM 302, Exams of Organic Chemistry

Virginia Commonwealth University (VCU)Organic Chemistry
Prof. Suzanne Ruder

Material Type: Exam; Professor: Ruder; Class: ORGANIC CHEMISTRY II; Subject: Chemistry; University: Virginia Commonwealth University; Term: Spring 2009;

Typology: Exams

Pre 2010

Uploaded on 03/18/2009

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CHEM 302 EXAM 2A NAME ____________________________
27 March 2007
Dr. Suzanne Ruder ID# or VCU email ____________________
Group #
On my honor, I have neither given nor received aid on this exam. ________________________
signature
INSTRUCTIONS: Read all questions carefully. If you have a question, raise your hand and
someone will assist you. Paper other than the exam paper and molecular models are not
permitted. Do your own work, and cover your answer sheets.
Part 1: Multiple Choice (4 pts each). Use the form provided to scratch off your answer. If your
answer is correct there will be a star; if your answer is not correct, scratch off your second
choice to receive partial credit for your answer. Scratch off questions 1-13 on your form.
1. In which electrophilic aromatic substitution reaction can unintended poly-substitution (i.e.,
disubstitution, trisubstitution, etc.) be a problem? In which electrophilic aromatic substitution
reaction can unintended poly-substitution (i.e., disubstitution, trisubstitution, etc.) be a problem?
A. Nitration
B. Friedel-Crafts acylation
C. Friedel-Crafts alkylation
D. Bromination
2. Rank the following in order of decreasing reactivity toward electrophilic aromatic
substitution (more reactive > less reactive).
CH3NO2OCH3
ABCD
A. D > C > B > A
B. D > B > A > C
C. B > D > A > C
D. C > D > B > A
3. Rank in order of decreasing favorability of hydration (more favorable > less favorable):
OO O O
CF
3
ABCD
A. C>D>B>A
B. D>C>B>A
C. C>B>A>D
1
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Partial preview of the text

Download Solved Multiple Choice Questions on Organic Chemistry II - Exam 2 | CHEM 302 and more Exams Organic Chemistry in PDF only on Docsity!

CHEM 302 EXAM 2A NAME ____________________________

27 March 2007 Dr. Suzanne Ruder ID# or VCU email ____________________ Group # On my honor, I have neither given nor received aid on this exam. ________________________ signature INSTRUCTIONS: Read all questions carefully. If you have a question, raise your hand and someone will assist you. Paper other than the exam paper and molecular models are not permitted. Do your own work, and cover your answer sheets. Part 1: Multiple Choice (4 pts each). Use the form provided to scratch off your answer. If your answer is correct there will be a star; if your answer is not correct, scratch off your second choice to receive partial credit for your answer. Scratch off questions 1-13 on your form.

1. In which electrophilic aromatic substitution reaction can unintended poly-substitution (i.e., disubstitution, trisubstitution, etc.) be a problem? In reaction can unintended poly-substitution (i.e., disubstitution, trisubstitution, etc.) be a problem? A. Nitration B. Friedel-Crafts acylation C. Friedel-Crafts alkylation D. Bromination 2. Rank the following in order of decreasing reactivity toward electrophilic aromatic substitution (more reactive > less reactive). CH 3 NO 2 OCH 3 A B C D A. D > C > B > A B. D > B > A > C C. B > D > A > C D. C > D > B > A 3. Rank in order of decreasing favorability of hydration (more favorable > less favorable): O (^) O O O CF 3 A B C^ D A. C>D>B>A B. D>C>B>A C. C>B>A>D

D. A>B>C>D

4. Which of the following dienes would you expect to be the most reactive in a Diels-Alder reaction? A. B. C. D. 5. Which of the following would you expect to be aromatic? A. B. C. D. NH O O 6. What is an acceptable name for the following? O 7. Which of the following is not a resonance structure involved in electrophilic aromatic bromination? A. B. C. D. 8. Which of the following statements are not true of benzene? A. All carbons are sp^2 hybridized. B. The carbon-carbon bond lengths alternate between single bonds and double bonds. C. The delocalized electrons form a circular pi-cloud above and below the ring. D. It is especially stable according to heats of hydrogenation data. A. ethyl isopropyl ketone B. 2-methyl-3-pentanone C. pentyl ketone D. A and B

D. A = Br 2 ; B = Mg ; C = CO 2 /H 2 O ; D = CH 3 Cl/AlCl 3 followed by H+/H 2 O

12. What would be the product of the following reaction? A. B. C. D. 13. What dieneophile was used to prepare the following compound via a Diels Alder reaction? O CN CN A. B. C. D. O NC CN CN CN C C CN CN

Part 2 : Write your answers to each question in the space provided. If extra space is needed, use the back of the page and indicate that you have done so on the front.

1. Draw the major organic products for each of the following reactions. Clearly indicate stereochemistry if necessary. a. (4 pts) Cl Cl O 2 N NO 2 NaOH b. (4 pts) O Ph 3 P=CHPh c. (4 pts) CH 3 1. KMnO 4 , H 2 O 2. H 3 O+ d. (4 pts) OCH 3 1. ClCOCH 3 , AlCl 3 2. Br 2 , FeBr 3 e. (4 pts) O H CH 3 NHNH 2

4. (6 pts) Draw the complete mechanism to account for the following reaction. Make sure to show curved arrows to indicate electron movement for each step, and draw all resonance forms of any intermediate. OH Br 2 FeBr 3 OH Br BONUS (6 pts) What are the products of the following sequence of reactions? O Cl AlCl 3

  • (^) A Zn (Hg) HCl

B

Cl 2 light

C

tBuONa D

  1. O 3
  2. Me 2 S E Br 2 ,FeBr 3 F