Extra Problems SN2 SN1 E2 E1

Extra Problems SN2 SN1 E2 E1 - O HO 45 o A (C 11 H 14 O 2 )...

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More practice with SN2, SN1, E2, and E1 reactions… Draw the major product in each of the following reactions: OTs NaOCH 3 CH 3 OH 25 o Br EtOH, 80 o KOtBu tBuOH 80 o Cl KCN DMSO 25 o Br 1. OH S 2. NaSH DMF, 25 o Et 3 N Cl O O *Step #1 of this process forms a tosylate (-OTs). What is the mechanism?
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2. Clearly draw an electron pushing mechanism for the following reaction. Identify which of the two alkenes is the major product. What type of reaction is this? O H 2 O 100 o C S O O
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3. Professor Snape asked Harry and Hermione to synthesize molecule A . They were given all necessary chemicals; the bromide provided was 100%ee R. Given: sodium acetate O NaO acetic acid O HO dimethylformamide (DMF) O H N and the starting bromide. Hermione does the following reaction: O NaO DMF, 25 o A (C 11 H 14 O 2 ) Br What is the structure of A (include stereochemistry)? What is the %ee of A ? What type of reaction is this (identify the mechanism)? Harry chooses to run this reaction instead.
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Unformatted text preview: O HO 45 o A (C 11 H 14 O 2 ) B ( C 9 H 10 ) Br He also obtains A but it differs in one key respect; also he gets a significant amount of B . How does Harrys A differ from Hermiones? Why? What is B (provide a structure)? 4. Circle the faster reaction in each pair. I EtOH 25 o OEt CH 3 I CH 3 OEt EtOH 25 o I NaSCH 3 DMSO 25 o SCH 3 I NaSCH 3 DMSO 25 o SCH 3 I NaOCH 3 DMSO 105 o I NaOCH 3 DMSO 25 o 5. Write the rate equation for the following reaction. Br NaSPh DMF SPh 6. Draw the transition state of the reaction shown in #5. 7. CHALLENGE: Compound X reacts approximately 500,000 times faster than Y . The stereochemical outcome also differs between X and Y . Explain the differences in reactivity. S Cl KCN EtOH S CN Cl KCN EtOH CN X Y very fast slow...
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Extra Problems SN2 SN1 E2 E1 - O HO 45 o A (C 11 H 14 O 2 )...

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