Midterm3November4thFall2022-1PM

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School

University Of Arizona *

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Course

241A

Subject

Chemistry

Date

Feb 20, 2024

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pdf

Pages

7

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1 CHEM 241a- 001 Midterm III (1-1:50 pm) November 4 th 2022 Question 1 (12 points): _____ Question 2 (08 points): _____ Question 3 (08 points): _____ Question 4 (06 points): _____ Question 5 (06 points): _____ Question 6 (08 points): _____ Question 7 (06 points): _____ Question 8 (08 points): _____ Question 9 (12 points): _____ Question 10 (12 points): _____ Question 11 (14 points): _____
2 Question 1: Name the following compounds. Question 2: Linalool, which is used in the fragrance industry, is found in both enantiomeric forms in nature with the R-isomer appearing in lavender and the S- isomer in coriander. Use names provides in bold to draw their structures .
3 Question 3: Provide the structure of the S N 2-product that would be formed when using 1 equivalent (right box) or excess (left box) of the nucleophile shown. Question 4: When the starting material shown is reacted with excess of POCl 3 /pyridine a wonderfully fragrant natural product called alpha-phellandrene is formed as the MAJOR product. Alpha-phellandrene is isolated from an Australian tree called eucalyptus radiata and is used extensively in the fragrance industry. Draw the structure of alpha-phellandrene (C 10 H 16 ) in the box below .
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4 Question 5: Epirubicin is an important natural product used as a chemotherapeutic agent for cancer. The sugar (carbohydrate) part of epirubicin is shown in the small box on left. Draw the most stable CHAIR conformation of this sugar in the box provided on right . Question 6: Epichlorohydrin is an important industrial chemical used as a starting material for making countless industrial products including epoxy glues. When epichlorohydrin is reacted with excess hydroxide (see below) another important product called glycerol (glycerine) is formed as the major product. Draw the structure of glycerol in the box provided .
5 Question 7: In class we learned how E2-reactions can be controlled. When the starting material shown is treated with the following bases different major E2 product is formed in each case. Clearly draw Major E2 product in each box. Question 8: Draw structures of MAJOR reaction products and provide reagent (chemicals) needed to convert the S N 1 product to the E2 product .
6 Question 9: In the space below draw the structures of ALL POSSIBLE E1 products. Question 10: Draw the structures of the MAJOR product of each reaction in boxes.
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7 Question 11: Draw the structures of MAJOR product for each reaction (NaH is a base)