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Smartwork Homework Answers

Chem 335 - Winter2000
Organic Chemistry II

Dr. Carl C. Wamser


Chapter 17 Homework Answers

Brown & Foote, pages 674 - 685 :
Problems 17.13 - 23 , 25 - 37 , 40 - 42 , 48

1. Write complete names for each of the following:

a)




b)




c)




2. A typical protein linkage is an amide bond (also called a peptidebond), such as might be found in N-methylacetamide. Proteins aretypically hydrolyzed in strong acid. Write a complete mechanismfor the acid-catalyzed hydrolysis of N-methylacetamide.




3. A typical fat has ester functional groups (most typically itis a triester between three fatty acids and glycerol). Glycerolis 1,2,3-propanetriol, and a fatty acid might be decanoic acid.Write the structure for the triester made from these components.




4. Using butanoic acid as the only organic starting material,show how to prepare:

a) 1-butanol




b) 1-bromobutane




c) butyl butanoate




d) butanamide




e) pentanoic acid

Chem 335 - Winter2000
Organic Chemistry II

Dr. Carl C. Wamser


Chapter 10 Homework Answers

Brown & Foote, pages 388 - 393:
Problems 10.7 - 19, 21, 22, 24 - 28

1. Give complete names for each of the following:

a)

(R),(E)-1-bromo-1-cyclopentylhex-4-en-2-yne

b)

(S),(E)-3-chloro-3,7,7-trimethyloct-4-en-1-yne

2. Write a complete mechanism for the addition of two equivalentsof HBr to propyne. Show all intermediates, and explain whetheror not Markovnikov's Rule applies to each addition.

3. Write a synthetic sequence that shows how to make cis-5-methyl-2-hexene.Allowable starting materials are acetylene and any alkyl halideor alcohol that has four carbons or fewer. You may also use anynecessary solvents or inorganic reagents.

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