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Chem_343_Spring_08_Problem_Set_4

Chem_343_Spring_08_Problem_Set_4 - 4 Looking down the...

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TA___________________ Chem 343, Problem Set #4 Name______________________________ 1. From compound A , five other compounds can be made using reactions that we have studied thus far. By each reaction arrow, provide the necessary reagents to carry out the most efficient synthesis of each molecule. Each synthesis should be executed in 1-5 steps. (15 points) HO H H CH 3 HO H H CH 3 HO H H CH 3 Br H H HO H H CH 3 HO H H OH Br OH O Br OH O O
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TA___________________ Chem 343, Problem Set #4 Name______________________________ 2. Draw the structure of the reacting partners that would need to come together to form the Diels Alder product shown below (5 pts) 3. Determine structures 1 - 6 using the information provided. (15 points) t -BuO 4 (C 16 H 15 Br) + 2 (C 5 H 8 O 2 ) 3 Ph Ph CH 3 OCH 3 O O 1 HCO 3 H NaOEt 5 NBS, h ! 6 (C 5 H 10 O 2 )
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TA___________________ Chem 343, Problem Set #4 Name______________________________
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Unformatted text preview: 4. Looking down the highlighted bonds, draw the most stable Newman projection using the provided templates. All stereochemistry must be properly recorded in each Newman Projection. (5 points) 5. True or False. Dibromocarbenes are generated through the reaction of Bromoform with potassium t-butoxide (2 points) 6. Provide the formula or structure of a solvent that would enhance the rate of an S N 2 governed nucleophilic substitution reaction (2 points) 7. Indicate why acetone would not be a suitable solvent to use for the transformation listed below. (2 points) O O 1) CH 3 MgCl. Acetone 2) NH 4 Cl OH OH 8. Indicate the stereochemistry (R/S, E/Z) at all the appropriate positions in the molecule below. (4 points) OH F F H OCH 3 HO...
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