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General Chemistry Principles, Patterns, and Applications, 2011

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1. Arrange CH 2 F + , CHCl + 2 , CH + 3 , <strong>and</strong> CHF + 2 in order of increasing stability. Explain your reasoning.<br />

2. Arrange CH 3 CH + 2 , CHBr + 2 , CH + 3 , <strong>and</strong> CHBrCl + in order of decreasing stability. Explain your reasoning.<br />

3. Identify the electrophile <strong>and</strong> the nucleophile in each pair.<br />

a. CH − 3 <strong>and</strong> Li +<br />

b. CH 3 ONa <strong>and</strong> formaldehyde<br />

c. H + <strong>and</strong> propene<br />

d. benzene <strong>and</strong> Cl −<br />

4. Identify the electrophile <strong>and</strong> the nucleophile in each pair.<br />

a. CH + 3 <strong>and</strong> Br −<br />

b. HC≡CNa <strong>and</strong> pentanal<br />

c. acetone <strong>and</strong> CN −<br />

d. (CH 3 ) 2 S <strong>and</strong> CH 3 I<br />

A N S W E R S<br />

1. CHF + 2 < CHCl + 2 < CH 2 F + < CH + 3 ; electronegative substituents destabilize the positive charge. The greater the<br />

number of electronegative substituents <strong>and</strong> the higher their electronegativity, the more unstable the<br />

carbocation.<br />

2.<br />

3.<br />

a. CH − 3 , nucleophile; Li + , electrophile<br />

b. CH 3 O − , nucleophile; formaldehyde, electrophile<br />

c. H + , electrophile; propene, nucleophile<br />

d. benzene, electrophile; Cl − , nucleophile<br />

4.<br />

S T R U C T U R E A N D R E A C T I V I T Y<br />

1. Draw Lewis electron structures of the products of carbon–hydrogen cleavage reactions. What is the charge<br />

on each species?<br />

2. Identify the electrophile <strong>and</strong> the nucleophile in each reaction; then complete each chemical equation.<br />

a. CH + 3 + Cl − →<br />

b. CH 3 CH=CH 2 + HBr →<br />

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

Saylor.org<br />

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