Assignment_7_Addition_to_carbonyls_Answers

Assignment_7_Addition_to_carbonyls_Answers - CHM 2120...

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CHM 2120 – Assignment 7 ANSWERS In this assignment: - Oxidation of alcohols - Nucleophilic addition to carbonyls - Acetals and derivatives - Wittig reaction - Baeyer-Villiger reaction 1. Provide names for the following compounds a) c) b) d) O O O HO 2 C O ( E )-hept-4-enal ( E )-4-methyl-3-propylhex-4-en-2-one (2 S ,3 S )-2,3-dimethylcyclooctan-1-one (best) cis -2,3-dimethylcyclooctan-1-one (acceptable) S S 4-ethyl-6-oxoheptanoic acid 2. Draw the structure corresponding to the following names: a. (E)-2-butenal b. 2-ethenylcyclohexanone c. 4-oxohexanal O H O O O CH 2 O Ph d. the benzyl carbocation e. 1-phenylethanone (acetophenone) 3. a. Give the product of the following reactions b. Explain, using a mechanism, why the product from parts a and b are different i. OH Na 2 Cr 2 O 7 H 2 SO 4 ,H 2 O O ii. OH PCC 2 Cl 2 O iii. 2 2 O 7 H 2 SO 4 2 O O
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Assignment 7 ANSWERS 2 iv. O PCC OH CH 2 Cl 2 4. Can Grignard reactions be conducted in protic solvents? Explain. NO. The Grignard reagent, such as methylmagnesium bromide would be destroyed through an acid/base reaction with the solvent (such as methanol). H 3 C MgBr H 3 C O H H 3 C H H 3 C O MgBr 5. How could you synthesize the following deuterium-labeled compound from bromobenzene, magnesium, dry ether, and deuterium oxide? Br 1. Mg MgBr 2. D O D D
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Assignment 7 ANSWERS 3 6. Give the products of the following reactions: *You should be able to draw the mechanism for each reaction.* O 1. CH
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Assignment_7_Addition_to_carbonyls_Answers - CHM 2120...

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