CHE201 - Chapter 3

CHE201 - Chapter 3 - Organic Chemistry, 6th Edition L. G....

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Chapter 3 Structure and Stereochemistry of Alkanes Organic Chemistry , 6 th Edition L. G. Wade, Jr.
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Chapter 3 2 Classification Review
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Chapter 3 3 Alkane Formulas • All C-C single bonds • Saturated with hydrogens • Ratio: C n H 2n+2 • Alkane homologs: CH 3 (CH 2 ) n CH 3 • Same ratio for branched alkanes => C H C H H HC H H H CH H H Isobutane, C 4 H 10 C H C H H C H H HH H H Butane, C 4 H 10
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Chapter 3 4 Common Names • Isobutane, “isomer of butane” • Isopentane, isohexane, etc., methyl branch on next-to-last carbon in chain. • Neopentane, most highly branched • Five possible isomers of hexane, 18 isomers of octane and 75 for decane! =>
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Chapter 3 5 Alkane Examples =>
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Chapter 3 6 IUPAC Names • Find the longest continuous carbon chain. • Number the carbons, starting closest to the first branch. • Name the groups attached to the chain, using the carbon number as the locator. • Alphabetize substituents. • Use di-, tri-, etc., for multiples of same substituent. =>
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Chapter 3 7 Longest Chain • The number of carbons in the longest chain determines the base name: ethane, hexane. (Listed in Table 3.2, page 82.) • If there are two possible chains with the same number of carbons, use the chain with the most substituents. C CH 3 2 3 2 2 3 CH CH 2 3 H 3 C H 3 C =>
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Chapter 3 8 Number the Carbons • Start at the end closest to the first attached group. • If two substituents are equidistant, look for the next closest group. 1 2 34 5 67 CH H 3 C 3 2 3 2 2 3 3 =>
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Chapter 3 9 Name Alkyl Groups •C H 3 -, methyl H 3 CH 2 -, ethyl H 3 CH 2 CH 2 -, n -propyl H 3 CH 2 CH 2 CH 2 -, n -butyl CH 3 2 3 sec- butyl 3 3 2 isobutyl 3 3 isopropyl C H 3 C 3 3 tert -butyl =>
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Chapter 3 10 Propyl Groups C H H H C H H C H H H n -propyl C H H H C H C H H H isopropyl H A primary carbon A secondary carbon =>
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Chapter 3 11 Butyl Groups C H H H C H C H H C H H H C H H H C H C H H H C H H n -butyl sec -butyl H H A primary carbon A secondary carbon =>
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Chapter 3 12 Isobutyl Groups C H H H C C H H C H H HH C H H H C C H H C H H H H H H A primary carbon A tertiary carbon => isobutyl tert -butyl
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CHE201 - Chapter 3 - Organic Chemistry, 6th Edition L. G....

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