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Chemistry Exam IV - December 1997 - Prof. Mark Forman, Exams of Organic Chemistry

Saint Joseph's University (SJU)Organic Chemistry

Prof. Mark Forman

The fourth examination for the chemistry 2311 course, held on december 8, 1997. The exam is composed of multiple-choice questions covering various topics such as iupac nomenclature, drawing structures, aromaticity, nitration, electrophilic aromatic substitution, and reagents for organic transformations.

Typology: Exams

Pre 2010

Uploaded on 08/18/2009

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CHEMISTRY 2311-EXAMINATION IV

DECEMBER 8, 1997

DR. MARK A. FORMAN

NAME:

QUESTION

POINTS

SCORE

1 6 _______

2 6 _______

3 8 _______

4 9 _______

5 4 _______

6 4 _______

7 6 _______

8 12 _______

9 9 _______

10 24 _______

11 12 _______

TOTAL _______

Discover Exams of Organic Chemistry Saint Joseph's University (SJU)

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CHEMISTRY 2311-EXAMINATION IV

DECEMBER 8, 1997

DR. MARK A. FORMAN

NAME:

QUESTION POINTS SCORE

1 6 _______

2 6 _______

3 8 _______

4 9 _______

5 4 _______

6 4 _______

7 6 _______

8 12 _______

9 9 _______

10 24 _______

11 12 _______

TOTAL _______

Provide an IUPAC name for each of the following compounds (6 points). a.) b.) CH CH^ CH^32 CH 2 CH CH^ CH^33 ______________________

CH 3 NO (^2) ______________________

Draw structures corresponding to each of the following IUPAC names (6 points). a.) p -chloroaniline b.) 3,5-dimethylphenol

a.) Circle all compounds that are expected to be aromatic. You may assume that all are planar (4 points).

b.) For each of the compounds in Part 3a.) above that wereexplain why they are not aromatic (4 points). not circled (i.e. not considered aromatic),

a.) The nitration of phenol leads to a mixture of ortho and para products. In the example shown below,only the para product and the intermediate carbocation leading to the para product are shown. Draw all other resonance structures for this intermediate carbocation (6 points). OH OH H NO 2

OH NO 2

b.) Draw the intermediate that is formed after meta attack. Dothis intermediate (3 points). not draw all of the resonance structures for

Would you expect (nitromethyl)benzene to be more or less reactive than toluene toward electrophilicaromatic substitution? Explain (4 points). CH 2 NO 2

Predict the product of each of the following reactions (24 points). a.) (^) OCH 3 Br

Br 2 , FeBr 3 b.) C(CH 3 ) (^3) KMnO 4 , H 2 O CH 3 c.) (^) NO 2 CH AlCl 3 C 3 Cl O

d.) C HNO 3 , H 2 SO 4 O CH 3

e.) (^) CH 3 Br 2 , FeBr 3 COOH

Show how you would accomplish each of the following syntheses, listing all required reagents andshowing all transformations (12 points). a.) (^) NO 2 Br

b.) (^) CH 2 CH 2 CH 3 Cl