Synthetic Organic Chemistry (CHMS4209)
BSc, Chemistry - CHMS
Semester: Resit
Level: 400
Year: 2018
REPUBLIC OF CAMEROON THE UNIVERSITY OF BAMENDA
Peace-Work-Fatherland
P. O. BOX 39 Bambili
Re-sit Examinations
School/Faculty:FS Department:_Chemistry Lecturer(s): JN Yong___
Course Code: _CHMS4209____Course Title: Synthetic Organic Chemistry credit
value: 6
Date: _Sept 11, 2018_______Halls: __ ________TIME: 12:30-2:30 (2 H)
Instructions: Answer all questions
1. (a) Using retrosynthetic analysis, give the most likely synthons and synthetic equivalents (SE) for the
following the target molecule (TM). (20 points)
(b) Using retrosynthesis, how would you prepare compound, A, beginning with a compound with at least four
carbon atoms. (12 points)
2. Draw the chair conformations. Draw the other chair conformation and circle the more stable conformation in
each pair. (6 points)
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3. Give the reagents/reaction conditions or product(s) for the following transformation. (8 points)
4. (a) Give the products of each step in the following conversion. (8 points).
(b) You remember the Nef reaction. Here is your chance to use it. Complete the following reaction. (10 point)
© Given the following protected compound, B, write the product when the A reacts with the following reagents.
(10 points)
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5. Supply the missing reagents required to accomplish the following synthesis. Be sure to control the
relative stereochemistry. (16 points)
(i)
(b) The retrosynthetic route for the synthesis of 5-nonanone from 1 -bromobutane is as follows
Show reagents and experimental conditions to bring about the synthesis.
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