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Midterm

CHM247H1 Study Guide - Midterm Guide: Alkyne, Acetylide, Stereochemistry

5 pages91 viewsSummer 2017

Department
Chemistry
Course Code
CHM247H1
Professor
Cecilia Kutas
Study Guide
Midterm

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Property of the University of Toronto Page 1 of 4
UNIVERSITY OF TORONTO
Faculty of Arts and Science
CHEMISTRY 247H1S
Introductory Organic Chemistry II
Term Test 1
February 4, 2015
6 7 pm
Total Marks Available: 150
Total Time: 1 hour
Permitted Aid: Molecular Model Kit
Before beginning, PRINT your surname, given name(s), student number and
CHM247 laboratory demonstrator group number on the answer sheet.
All answers for credit must be entered legibly, preferably in blue or black ink or
in pencil, in the correct place on the answer sheet within the given time. Do not
write in the margin of the answer sheet. Do not write in red ink.
No extra time will be given to transfer answers to the answer sheet.
Please ensure that you have all 4 test pages. There are spectroscopic correlation
tables attached to the back of the exam for your reference. You may use the back
of the test pages for rough work.
Read all questions carefully before answering them.
Good luck
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Property of the University of Toronto Page 2 of 4
CHM 247H1S Test 1: February 4, 2015
*Write all answers for credit on the answer sheet within the time allowed.*
1. Chemical Knowledge and Classification (8 marks)
(a) Consider the compounds below and circle (on the answer sheet), the ones that could have been made
in one transformation from a terminal alkyne (including work-up, ex. 1. O3, 2. Zn/HOAc counts as one
transformation). (4 marks)
(b) Consider the compounds below and circle (on the answer sheet), the ones that would react with an
acetylide anion. (4 marks)
2. Nomenclature (11 marks)
On the answer sheet, draw an unambiguous structure for the name given below.
(R)-6-methyloct-1-en-3-yne
3. Reactions (21 marks)
Draw the major product(s) or provide the required reagents for each of the following reactions on the
answer sheet. Be sure to show stereochemistry where appropriate (7 marks/reaction).
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