CHEM 281 - 2011-3 Problem Set 8 - WEEK 9

CHEM 281 - 2011-3 Problem Set 8 - WEEK 9 - CHEMISTRY 281-4...

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1 CHEMISTRY 281-4 (2011-3). Dr. Pete Wilson ORGANIC CHEMISTRY I: PROBLEM SET 8. WEEK 9 – LECTURE 24 (Wednesday, 2 November) Problems ¾ For discussion in tutorials (Week 10 ) in addition to any other general questions you may have about the course material. 1. Please revisit Practice Interterm Examination 1 and solve questions 2 and 7. These questions reflect the conformations of cyclohexanes and stereochemical assignments which will be topics of your Interterm Examination II. 2. Selected Problems (lots….) from Past Inter-term II Examinations are provided below. Notes: Interterm Examination II ( 10:30 a.m. Wednesday, November 16, 2011 ) will focus on the topics covered in class between Week 5 and up to the end of Week 10. However, an understanding of earlier material is essential. These questions are representative, and beyond (because of curriculum changes), of what you may expect in your Interterm Examination II. We have not covered all of the topics that relate to these questions in class yet – so do the questions that relate to what I am discussing in class in Week 5 through 10.
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2 Representative Past Inter-term Examination II Questions 1. Consider the alcohol shown below (two equivalent structures are provided for clarity) and answer the following six questions (9 marks). H OH H Me Me H OH HM e Me = CH 3 1. a). Provide the IUPAC name of this alcohol (you should include in the name the R / S assignments for the two stereogenic centres) (4 marks). 1. b). Assuming that the alcohol undergoes an S N 2 reaction with hydrogen bromide (HBr) draw the molecular structure of the reaction product (1 mark). 1. c). If the alcohol undergoes an S N 1 reaction with hydrogen bromide (HBr) an additional reaction product would be formed (see above: question 1. b).). Draw the molecular structure of the reaction product (1 mark). 1. d). What is the stereochemical relationship between these two reaction products (see above: question 1. b). and c)., i.e. are they diastereomers or enantiomers) (1 mark)? 1. e). Draw the molecular structure of the product formed on reaction of the alcohol with the oxidizing agent, chromic acid (H 2 CrO 4 ) (1 mark).
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3 1. f). Draw the molecular structure of the enantiomer of the alcohol (1 mark). 2. Consider the alkene shown below and answer the following nine questions (15 marks). 2. a). Reaction of the alkene with osmium tetroxide (OsO 4 ) and water affords two diols as a racemic mixture (50:50). Draw the molecular structure of these two reactions products. You should pay particular attention to the stereochemistry (2 marks). 2. b). Draw the molecular structure of the product of the reaction of the alkene with ozone (O 3 ) on subsequent treatment with dimethyl sulfide (Me 2 S) or zinc/acetic acid (Zn/CH 3 CO 2 H) (1 mark). 2. c). Draw the molecular structure of the product of the reaction of the alkene with hydrogen bromide (HBr) (1 mark).
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This note was uploaded on 12/07/2011 for the course CHEM 281 taught by Professor Williams during the Fall '11 term at Simon Fraser.

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CHEM 281 - 2011-3 Problem Set 8 - WEEK 9 - CHEMISTRY 281-4...

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