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9 Solved Questions on the Stereochemistry - Final Exam | CHEM 341, Exams of Organic Chemistry

Material Type: Exam; Professor: Walker; Class: ORGANIC CHEMISTRY 1-LEC; Subject: CHEMISTRY; University: SUNY-Potsdam; Term: Unknown 1989;

Typology: Exams

Pre 2010

Uploaded on 08/09/2009

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Chem 341
Practice Final Examination M. Walker
YOUR NAME ________________________________________________
3 hours duration, 360 points total. [NOTE: YOUR FINAL WILL ONLY BE TWO
HOURS LONG, AND SO IT WILL BE SHORTER THAN THIS ONE].
1. Give a systematic name for each of the following compounds, including
stereochemistry:
Cl
Cl H
2. Which is the most stable from each set of three related structures?
+
+
+
CH3
CH3
CH3
3. Draw a meso form and two enantiomers of 3,4-dimethylhexane:
pf3
pf4
pf5

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Chem 341 Practice Final Examination M. Walker

YOUR NAME ________________________________________________

3 hours duration, 360 points total. [NOTE: YOUR FINAL WILL ONLY BE TWO HOURS LONG, AND SO IT WILL BE SHORTER THAN THIS ONE].

  1. Give a systematic name for each of the following compounds, including stereochemistry:

Cl

Cl H

  1. Which is the most stable from each set of three related structures?

CH (^3)

CH 3 CH^3

  1. Draw a meso form and two enantiomers of 3,4-dimethylhexane:
  1. Predict the major product(s) of the following reactions (indicate stereochemistry):

Ph

Br 2 , H 2 O

(i) O (^3)

(ii) (CH 3 ) 2 S

CH 3 C CH

Cl (^2)

Br

HCl

(a)

(b)

(c)

(d)

(e)

hv

(f) heat

NBS

heat

(g)

(h) (i) H 2 O, Hg(OAc) (^2)

KO tBu

(ii) NaBH 4

(i) NaNH 2

(ii) CH 3 I

  1. Show how you might perform either one of the syntheses shown below. You must use the starting material given as your sole source for all carbons in the product (you need not synthesize reagents which are not incorporated, however)

EITHER (a) CH 3 CH 3 Cl (^) (Racemic,but only the pure cis isomer with no trans)

OR

(b)

Ph C CH

CH (^2) Ph CH^2 C^ C^ Ph

2

  1. 1-Chlorohexane reacts with - OCH 3 ion as shown:

(a) Draw an energy curve for the reaction, and indicate which points on the curve correspond to any intermediates or transition states.

(b) Write a rate equation for the reaction.

(c) Which would you expect to be more reactive as a substrate in this reaction, 1-chlorohexane or 1-bromohexane?

(d) What functional group has been formed in this reaction?