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General Chemistry Principles, Patterns, and Applications, 2011

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. cyclohexanol + H 2 SO 4<br />

7. A Grignard reagent can be used to generate a carboxylic acid. Show the mechanism for the first step in this<br />

reaction using CH 3 CH 2 MgBr as the Grignard reagent. What is the geometry about the carbon of the –CH 2 of<br />

the intermediate species formed in this first step?<br />

8. Draw a molecular orbital picture showing the bonding in an amide. What orbital is used for the lone pair of<br />

electrons on nitrogen?<br />

9. What is the product of the reaction of<br />

a. acetic acid with ammonia?<br />

b. methyl acetate with ethylamine, followed by heat?<br />

10. Develop a synthetic scheme to generate<br />

a. 1,1-dichloroethane from 1,1-dibromoethane.<br />

b. 2-bromo-1-heptene from 1-bromopentane.<br />

A N S W E R S<br />

1. 2,2-dibromobutane<br />

2.<br />

3.<br />

4.<br />

5.<br />

a. C 6 H 5 OC 2 H 5 + NaCl<br />

b. 1-propanol + NaCl<br />

6.<br />

7.<br />

8.<br />

9.<br />

a. CH 3 CO − 2 NH + 4 (an acid-base reaction)<br />

b. CH 3 CONHC 2 H 5 + CH 3 OH<br />

10.<br />

Saylor URL: http://www.saylor.org/books<br />

Saylor.org<br />

2303

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