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Name: ________________________________ ID #: ________________________________

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EXAM I Organic Chemistry 2302-001 February 20th, 2013 ! Exam is 7 pages including a Periodic Table and Spectroscopy Tables (make sure that you have them all). ! Do not open your exams until instructed to do so. ! Have your ID in hand when you come forward to turn in your exam. ! Place your last name on all pages of exam in case your exam gets separated. ! You may NOT use calculators, notes, or models for the exam. ! Please raise your hand if you have a question and a TA or I will assist you. ! You will be given 50 minutes to complete your exam. When time is called, all pens/pencils are to be put down and no more written work done. Points will be deducted from exams of those who keep working. ! Read each question carefully and be sure to answer all parts of each question.

1.) 2.) 3.) 4.) 5.) 6.) 7.) 8.)

___________/ 8 pts ___________/ 12 pts ___________/ 6 pts ___________/ 9 pts ___________/ 27 pts ___________/ 12 pts ___________/ 12 pts ___________/ 14 pts

Total ___________/ 100 pts

Last Name: ___________________________

1. Nomenclature. 8 points Draw the structure corresponding to each name. Indicate stereochemistry where appropriate. a. 1-cyclopentene carboxylic acid b. 4-bromo-2-ethylaniline

c. Zwitterion form of the amino acid L-Serine d. (2Z, 4E)-3-methoxy-2,4-hexadiene (R = CH2OH) "-carbon has S configuration (s-cis conformation)

2. Fill in the Blank. Identify each of the following compounds as aromatic, antiaromatic or nonaromatic (assume all are planar). 12 points

i.
N

aromatic antiaromatic nonaromatic

ii.
O

aromatic antiaromatic nonaromatic

iii.

aromatic antiaromatic nonaromatic

iv.

O N

aromatic antiaromatic nonaromatic

EXAM I

Perkins, Chem 2302-001 Spring 2013

Last Name: ___________________________

3. Multiple Choice. For each of the following questions, clearly circle the correct answer(s). Some questions may have more than one answer, so circle all that apply. 6 points a. Para-substitution of anisole leads to the stabilized carbocation on the left, which of the structures on the right are resonance structures of the molecule on the left?
H 3C O H 3C O H 3C O H 3C O H 3C O

H CH3

CH3

H CH3

CH3

H CH3

b. Which of the following rings will undergo an electrophilic aromatic substitution reaction faster than benzene?
O OCH3 Br SO3H O HN

4. Acidity. For each of the following pairs of molecules below, determine which proton (Ha or Hb) is more acidic (circle it) and explain your selection. Vague explanations like more stable are not enough, explain why the conjugate base is more stable. 9 points O O a. Ha Hb WHY? vs. O O
O2N

b. H

Ha vs.

Hb

WHY?

c.

N Ha

vs.

Hb N H

WHY?

EXAM I

Perkins, Chem 2302-001 Spring 2013

Last Name: ___________________________

5. Reactions. For each of the following reaction schemes, fill in the necessary starting materials, reagents or products in the boxes provided below paying careful attention to stereochemistry and regiochemistry. If the reaction produces a pair of enantiomers, draw one stereoisomer and indicate the presence of the other by including + enantiomer. 27 points a.
SO3H HNO 3, H 2SO4

b.
O + O H H heat

c.
Cl 2, FeCl 3 O KMnO 4

d.
heat + H 3CO CN CN

e.
Cl O AlCl3 NBS ROOR

EXAM I

Perkins, Chem 2302-001 Spring 2013

Last Name: ___________________________

6. Electrophilic Addition to a Diene. The addition of one equivalent of HBr to 2,3dimethylcyclopentadiene gives two products X and Y. 12 points
1 eq H-Br X + Y

a. Draw the two products of the reaction corresponding to 1,2-and 1,4-addition in the appropriate boxes provided. Dont worry about stereochemistry. 6pts

1,2 Addition Product

1,4 Addition Product

b. Draw a reaction coordinate diagram to describe the formation of the two products. You only need to draw the second step of the reaction (start your diagram from the resonancestabilized carbocation intermediate). Use your diagram to explain why one product is favored in under kinetic conditions (lower temperature) while the other is favored under thermodynamic conditions (higher temperature). Be sure to clearly label the products on your diagram. 6pts

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Last Name: ___________________________

7. Mechanism. Draw a stepwise mechanism for the following reaction. Be sure to include all reactive intermediates and resonance structures. 12 points
+ Cl AlCl3

8. Synthesis. How would you synthesize 1-nitro-3-propenylbenzene starting from benzene? You may use any organic and inorganic reagents necessary. 14 points ! !

1-nitro-3-propenylbenzene NO 2

EXAM I

Perkins, Chem 2302-001 Spring 2013

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Last Name: ___________________________

EXAM I

Perkins, Chem 2302-001 Spring 2013