Chapter 3 - Wade_7th Ed

Chapter 3 - Wade_7th Ed - Introduction to General and...

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Chapter 3 Structure and Stereochemistry of Alkanes Introduction to General and Organic Chemistry II Dr. David P. Brown Department of Chemistry
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Chapter 3 2 Hydrocarbons are molecules that are made of carbon and hydrogen ONLY. Hydrocarbons
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Chapter 3 3 Alkanes The alkanes belong to the group of saturated hydrocarbons. General Formula: C H H C H H H C C H H H H H H b.p. -160 o C - 89 o C
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Chapter 3 4 Shapes of Alkanes
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Chapter 3 5 The Butanes C H H C H H C H H C H H H H Butane, C 4 H 10 C H H C C H H H C H H H H H Isobutane, C 4 H 10
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Chapter 3 6 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 7 Pentanes C H H C H H C H H C H C H H H H H n -pentane, C 5 H 12 C H H C C H H C H H H H H C H H H isopentane, C 5 H 12 => C CH 3 CH 3 H 3 C CH 3 neopentane, C 5 H 12
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Chapter 3 8 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 9 Longest Chain The number of carbons in the longest chain determines the base name: ethane, hexane. ( Listed in Table 3.2, page 84.) If there are two possible chains with the same number of carbons, use the chain with the most substituents . C CH 3 CH 2 CH 3 CH CH 2 CH 2 CH 3 CH CH 2 CH 3 H 3 C H 3 C =>
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Chapter 3 10 Main Chain Two longest chains of equal length: use the chain with the greatest number of substituents.
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Chapter 3 11 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 3 4 5 6 7 CH H 3 C CH 3 CH CH 2 CH 3 CH 2 CH 2 CH CH 3 CH 3 =>
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Chapter 3 12 Name Alkyl Groups CH 3 -, methyl CH 3 CH 2 -, ethyl CH 3 CH 2 CH 2 -, n -propyl CH 3 CH 2 CH 2 CH 2 -, n -butyl CH 3 CH CH 2 CH 3 sec- butyl CH 3 CH CH 3 CH 2 isobutyl CH 3 CH CH 3 isopropyl C H 3 C CH 3 CH 3 tert -butyl =>
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Chapter 3 13 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 H removed from primary carbon H removed from secondary carbon =>
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Chapter 3 14 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 15 Isobutyl Groups C H H H C C H H C H H H H 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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16 Alphabetizing Alphabetize substituents by name.
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This note was uploaded on 09/25/2010 for the course CHE 2230 taught by Professor Graham during the Fall '09 term at St. John's.