CHEMISTRY 2311-EXAMINATION II
OCTOBER 17, 1997
DR. MARK A. FORMAN
NAME:
QUESTION
POINTS
SCORE
1 6 _______
2 9 _______
3 7 _______
4 15 _______
5 9 _______
6 6 _______
7 15 _______
8 27 _______
9 6 _______
TOTAL _______
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9 Questions on Heat of Hydrogenation - Exam 2 | CHM 2311, Exams of Organic Chemistry
Material Type: Exam; Professor: Forman; Class: Organic Chemistry I; Subject: Chemistry; University: Saint Joseph's University; Term: Fall 1997;
Typology: Exams
Pre 2010
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CHEMISTRY 2311-EXAMINATION II
OCTOBER 17, 1997
DR. MARK A. FORMAN
NAME:
QUESTION POINTS SCORE
1 6 _______
2 9 _______
3 7 _______
4 15 _______
5 9 _______
6 6 _______
7 15 _______
8 27 _______
9 6 _______
TOTAL _______
- Give the structural formula for each of the following compounds (6 points). a.) cis -2-hexene b.) 4-chloro-2-heptyne
- Provide IUPAC names for the following compounds (9 points). a.) b.) c.) H 3 C CH 3
H 3 CC C Br CH 2 CH 3
CH (^3) CCHCH^32 C CH H 3 C CH 3
- a.) Match each alkene shown below with the appropriate heat of hydrogenation. Place the letter in theblank to the right of the alkene (3 points). A. -30.3 kcal/mol B. -28.5 kcal/mol C. -26.9 kcal/mol
b.) Which alkene is most stable? Why? (4 points).
- Select the best answer for each of the following (15 points). a.) Which of the following substituents has the highest priority using the Cahn-Ingold-Prelog sequencerules? I. -CH 3 II. -CH 2 CH 3 III. -CH=CH 2 IV. -CH 2 OH b.) Which of the following carbocations is most stable? I. II. III. IV.
c.) Which of the following predicts that in electrophilic addition of HX to alkenes, the H adds to thecarbon already possessing the greater number of hydrogens? I. Markovnikov’s Rule II. Hammond Postulate III. Cahn-Ingold-Prelog Rules IV. Simmons-Smith d.) Which of the following is the strongest acid? I. CH 3 CH 3 II. CH 2 =CH 2 III. CH=CH IV. CH 4 e.) Which of the following radicals is the most stable? I. II. III. IV.
- Predict the product of each of the following reactions. Provide a stereochemically explicit product inthose reactions marked with a *. (27 points) *a.) CH 3 C C CH 3 H^2 , Lindlar catalyst b.) (^) CH 2 CH (^3) H-Cl
*c.) (^) CH 3 CH 3
H 2 , Pd
d.) (^) 1. Hg(OAc) 2 , H 2 O, THF CH 3 CH 2 CH=CH (^2) 2. NaBH 4 e.) CH 3 CH 2 C C H^ 1. HBSia2. H 2 O 2 , HO-^2 , THF f.) HH 33 CC^ C^ CHCH^3 1. O^ 2. Zn, AcOH^3 g.) CH C C H 3 CH 2 2 H-Cl h.) 1. BH
- H^3 , THF 2 O 2 , HO-
- Show how you would accomplish the following synthetic transformation. You should need only two orthree steps. (6 points) CH 3 C C H H 3 CH C CHCH^3