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Chem 2201 F2021 Exam #3: Organic Chemistry Exam Temple university - Prof. Steven Fleming, Exams of Organic Chemistry

A comprehensive organic chemistry exam for chem 2201, fall 2021, TEMPLE UNIVERSITY. It includes a variety of questions covering topics such as iupac nomenclature, stereochemistry, reaction mechanisms, and synthesis. The exam provides detailed solutions and explanations for each question, making it a valuable resource for students studying organic chemistry.

Typology: Exams

2020/2021

Available from 01/19/2025

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Name_________________
Chem 2201
Fall 2021
Exam #3
(10 pts) 1. Provide the IUPAC or common name for the following compounds (don't forget R, S or E, Z assignments
where applicable):
a.
Name_____________________________________
b.
Name _____________________________________
c.
Name _____________________________________
d.
Name _____________________________________
e.
Common name ________________________________
(14 pts) 2. Recall that the photo-chlorination reaction (Cl2 and light) is not very selective. There are 4 monochloro
products (each one has a formula of C4H7Cl) in the reaction shown. Draw them.
A B C D
Which would be chiral products (circle the ones that are chiral). A B C D
Would your chiral products be formed as single enantiomers or as racemic mixture?
O
O
HO
Cl
Br
OH
Cl2
hυ
Racemic mixture
phenol
[(2S)-1-chloro-3-methylbutan-2-yl]benzene
1,2-epoxy-3-ethoxylcyclopentane OR 2-ethoxy-6-oxabicyclo[3.1.0]hexane
(4Z)-2-methylhex-4-en-2-ol
(6S)-6-bromo-5,5-dimethyloct-3-yne
pf3
pf4

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Name_________________ Chem 2201 Fall 20 21 Exam # (10 pts) 1. Provide the IUPAC or common name for the following compounds (don't forget R , S or E , Z assignments where applicable): a. Name_____________________________________ b. Name _____________________________________ c. Name _____________________________________ d. Name _____________________________________ e. Common name ________________________________ (1 4 pts) 2. Recall that the photo-chlorination reaction (Cl 2 and light) is not very selective. There are 4 monochloro products (each one has a formula of C 4 H 7 Cl) in the reaction shown. Draw them. A B C D Which would be chiral products (circle the ones that are chiral). A B C D Would your chiral products be formed as single enantiomers or as racemic mixture? O O HO Cl Br OH Cl 2 hυ

Racemic mixture

phenol

[(2S)-1-chloro-3-methylbutan-2-yl]benzene 1,2-epoxy-3-ethoxylcyclopentane OR 2-ethoxy-6-oxabicyclo[3.1.0]hexane (4Z)-2-methylhex-4-en-2-ol (6S)-6-bromo-5,5-dimethyloct-3-yne

Score_____ (24 pts) 3. Predict the major product for each reaction. Show stereochemistry where relevant. a. b. c. d. e. f. g. h. ethanol H 2 poisoned Pd

  1. peroxy acid THF
  2. NaOCH 2 CH 3 HOCH 2 CH 3
  3. O 3 CH 2 Cl 2
  4. Zn
  5. BH 3 THF
  6. NaOH, H 2 O 2 THF
  7. OsO 4
  8. H 2 O H 2 O Br 2 excess Br 2 THF NBS THF hυ

(1 0 pts) 7. Determine the structure of compound F , whose NMR is shown below. The formula for D is C 5 H 12 O. There is a broad band at 3400 cm-^1 in the IR spectrum of F. Assign the NMR signals to the structure you propose. Compound F 5 4 3 2 1 0 PPM .05 .10 .05 .11. this signal shifts with D 2 O