Exam 3 Practice
Exam 3 Practice CHEM 270
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Popular in Chemistry
This 10 page Study Guide was uploaded by Danielle Collier on Monday April 18, 2016. The Study Guide belongs to CHEM 270 at California State University Chico taught by Dr. Carolynn Arpin in Spring 2016. Since its upload, it has received 10 views. For similar materials see Organic Chemistry in Chemistry at California State University Chico.
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Date Created: 04/18/16
CHEM 270-01 Fall 2014 Test #3 By signing below you are agreeing to the following statement: I will not cheat. Signed: __________________________________________________________ Printed Name: _________________________________________________________ Student Number: ____________________________________ Although you may use scratch paper, answers on additional sheets will not be graded. Please write your last name at the top of each page in this test packet in case it comes apart. GOOD LUCK!! November 14 , 2014 Page 2: 26 points Time Limit: 50 minutes Page 3: 22 points Page 4: 26 points Page 5: 34 points Total Possible: 108 points Last Name: ___________________________ CHEM 270-01 Test #3 1. For each pair of reactions below, indicate which starting material would react faster. Explain each prediction. (16 points) a) b) 2. Using curved arrows to show the movement of electrons, provide the mechanism for step (i) of the reaction below and then provide the major product(s). Include stereochemistry where appropriate, and note a racemic mixture if applicable. (10 points) Page 2 of 5 Score: _______ Last Name: ___________________________ CHEM 270-01 Test #3 3. a) Using curved arrows to show the movement of electrons, provide the mechanism corresponding to the formation of one of the products below (either one – your choice). (8 points) b) Predict the distribution of products in the above reaction (percent of each product that forms), assuming that the first step of the mechanism is the rate determining step. Explain your prediction. (5 points) 4. For the reaction below, the stereochemistry of the starting material dictates the formation of the Z alkene upon E2 elimination. (9 points) a) Provide the Newman projection of the starting material’s E2-reactive conformer with the appropriate stereochemistry so that the Z alkene product is formed. b) Now re-draw the wedge-and-dash structure of the starting material, complete with stereochemistry at the asymmetric carbons. Page 3 of 5 Score: _______ Last Name: ___________________________ CHEM 270-01 Test #3 5. Provide the missing compounds and/or reagents in the following reactions. (17 points) a) b) c) d) e) 6. Predict the major organic product(s) of the following reactions. Be sure to include stereochemistry where appropriate and note racemic mixtures. (9 points) a) b) c) Page 4 of 5 Score: _______ Last Name: ___________________________ CHEM 270-01 Test #3 7. a) Using curved arrows to show the movement of electrons, provide the mechanism to predict the major product of the reaction below. Don’t worry about stereochemistry when drawing your mechanism. (6 points) b) Now, taking into account stereochemistry of the reaction in part (a), explain whether or not both enantiomers of the product are formed and why. (3 points) c) Considering the mechanism you drew in part (a), provide the two diastereomeric products of the reaction below (note the different starting material). Label which is the major and the minor diastereomer. Explain your prediction for the major and minor diastereomer. (8 points) 8. Using a series of synthetic reaction steps, how could you carry out the following syntheses? Write the reagents and products for each step in the spaces provided. (17 points) a) b) Page 5 of 5 Score: _______
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