PS9_due_111722_final_corrected

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University Of Arizona *

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12A

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Chemistry

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Feb 20, 2024

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8

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Chem 12A 2022 Problem Set 9. Due 11/17/22 at the beginning of lecture. Assigned problems from Karty. Predict products. Ed 3: 13.21 c and d, 13.24a, 13.28 b and c; Ed 2:12.27a, 12.42c and d, 12.45a, 12.52b and c; Ed 1:12.29 Synthesis. Ed 3. 13.29; 11.34, Ed 2: 12.53, 13.45 Ed 1: 12.30, 12.31,13.29, 13.38 1,2 and 1,4 addition for bromination. Ed 3: 13.17; Ed 2: 12.38 Ed 1: 12.38 For Ed 3: this is Ed. 2 12.27a Additional Problems: 1. Predict the major organic products of the following reactions. Draw all stereoisomers that are formed. a. b. 1
Chem 12A 2022 c. d. e. 2
Chem 12A 2022 2. Fill in the reagents required for the following reactions. More than step may be required to complete the transformation. a. b. 3
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Chem 12A 2022 3. Consider the reaction shown below. a. Predict the structure(s) of the product(s) and draw them in the boxes above. b. Show a mechanism for the first step of the reaction leading to the mercurinium intermediate. c. Explain why the reaction proceeds exclusively through the mercurinium intermediate shown above. 4
Chem 12A 2022 4. Fill in each of the boxes below with the correct products or reagents. a. b. 5
Chem 12A 2022 5. Consider the three reactions shown below. a. Write a mechanism with arrows for each of the reactions. b. For each reaction, draw and label the initial sets of orbitals involved as the alkene reacts with the electrophile. You will draw the orbitals involved in the alkene electrons reacting with the electrophile. Identify whether each orbital is the HOMO or LUMO. i. ii. iii. i. ii. iii. 6
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Chem 12A 2022 c. For each reaction, draw a reaction energy diagram. Include sketches of all starting materials, products, and intermediates. Label the axes. 5. Consider the reaction shown below. a. Draw the structures of intermediate(s) A and product(s) B. b. Draw the mechanism to form intermediate A. i. ii. iii. 7
Chem 12A 2022 6. Synthesize the following products from the indicated starting materials and any additional reagents. + enantiomer 8