exam3_f00 - the structure and explain why only one product...

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Chem 12A EXAM #3 Name __________________ Dr. Harrison 1. (12 pts) Name the following compounds. a) b) ________________________________ _____________________________ c) d) Ph H ________________________________ _____________________________ 2. (10 pts) β -Ocimene is a natural product with a pleasant odor. Based on the information provided below, deduce the structure of β -Ocimeneand and calculate the degrees of unsaturation. __________ b-ocimene (C 10 H 16 ) H 2 , Pt 2,6- dimethyloctane 1. O 3 2. (CH 3 ) 2 S CH 2 O + CH 3 COCH 3 + CH 3 COCHO + OHCH 2 CHO 3. (12 pts) Suggest a possible synthesis of the following product by starting with an alkyne and an alkyl halide. Write all reactants and reagents.
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4. (16pts) Write the mechanism for the following reaction. a. OH O Br Br-Br + Br - b. CH 3 H 3 C Na, NH 3 CH 3 H 3 C 5. (16 pts) Each of the following reactions give only one major elimination product. Draw
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Unformatted text preview: the structure and explain why only one product is isolated. a) Br NaOH b) Br Br-OH c) Br NaOH NaOC(CH 3 ) 3 6. (15 pts) Provide the reagents necessary to complete the following transformations. The reaction takes more than one step. Show each intermediate in your reaction scheme. a) Br OH OH b) OH Br c) H O + Alkyne OH H H O 7. (10 pts) Predict which compound is more stable and give two reasons to support your answer. 8. (22 pts) For each reaction below replace X with the missing reactant(s), reagents, or product(s). Show all stereochemistry where appropriate. a) 1. O 3 2. (CH 3 ) 2 S X KMnO 4 Hot, conc. X b) excess H 2 Pt X c) 1. Br 2 2. H 2 O X d) OH OH OsO 4 H 2 O 2 X e) Br Br NaNH 2 KOH 150 0 C 200 0 C X X f) OH OH X X g) MCPBA H 3 O + 1) Br 2 X X 2) H 2 O...
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This note was uploaded on 09/02/2011 for the course CHEM 12a taught by Professor Harrison during the Spring '11 term at West Valley.

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exam3_f00 - the structure and explain why only one product...

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