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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

Uploaded on 08/19/2009

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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 _______
pf3
pf4

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Download 9 Questions on Heat of Hydrogenation - Exam 2 | CHM 2311 and more Exams Organic Chemistry in PDF only on Docsity!

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 _______

  1. Give the structural formula for each of the following compounds (6 points). a.) cis -2-hexene b.) 4-chloro-2-heptyne

  1. 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


  1. 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).

  1. 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.

  1. 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

  1. H^3 , THF 2 O 2 , HO-
  2. 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