SCHOOL OF DISTANCE EDUCATION
UNIVERSITI SAINS MALAYSIA
ACADEMIC SESSION 2013-2014
JIK 224 ORGANIC CHEMISTRY 1
ASSIGNMENT 1
DR. SUMIYYAH SABAR
FINAL SUBMISSION DATE: 30th DECEMBER 2014 (TUESDAY)
Please note that plagiarism will not be tolerated. Answers that are copied directly from books, internet or a friends assignment will get zero mark. All workouts MUST be shown. Do not re-write your questions in your answer sheet. All assignments must be submitted ONLINE through the e-portal.
1. For each compound drawn below:
(a) Label each OH, Br, and CH3 group as axial or equatorial.
(b) Classify each conformation as cis or trans.
(c) Translate each structure into a representation with a hexagon for the six-membered ring, and wedges and dashes for groups above and below the ring.
(d) Draw the second possible chair conformation for each compound.
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2. Draw all possible stereoisomers for each cycloalkane. Label pairs of enantiomers and diastereomers. Label any meso compound.
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3. Suppose you have compounds AD at your disposal. Using these compounds, devise two different ways to make E. Which one of these methods is preferred, and why?
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4. Treatment of 2,2-dibromobutane with two equivalents of strong base affords 1-butyne and 2-butyne, as well as a small amount of 1,2-butadiene. Draw a mechanism showing how each compound is formed. Which alkyne should be the major product?
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5. Give the IUPAC name for each compound.
(a)
(b)
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(c)
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(d)
~ The End ~
Sue
30/11/14