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Chap-3A - Chapter 3 Structure and Stereochemistry of...

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Chapter 3 Structure and Stereochemistry of Alkanes
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Chapter 3 2 3-2 Molecular Formulas of Alkanes 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 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 3 3-3A 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! 3-3 Nomenclature of Alkanes
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Chapter 3 4 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 5 Longest Chain The number of carbons in the longest chain determines the base name: ethane, hexane. (Listed in Table 3.2, page 81.) 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 3-3B IUPAC Names The systematic way to name all organic compounds.
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Chapter 3 6 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 7 Name Alkyl (Substituent) 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 8 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 9 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 10 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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Chapter 3 11 Alphabetize Alphabetize substituents by name. Ignore di-, tri-, etc. for alphabetizing. CH H 3 C CH 3 CH CH 2 CH 3 CH 2 CH 2 CH CH 3 CH 3 3-ethyl-2,6-dimethylheptane •Prefixes used for the same type of (>2) alkyl groups Di = 2, Tri = 3, Tetra = 4, Penta = 5
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Chapter 3 12 Complex Substituents If the branch has a branch, number the carbons from the point of attachment. Name the branch off the branch using a locator number. Parentheses are used around the complex branch name. 1 2 3 1-methyl-3-(1,2-dimethylpropyl)cyclohexane
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Chapter 3 13 IUPAC Names: Summary (1) Find the longest continuous chain of carbon atoms. This is the base name of the compound. (2) Number the longest chain beginning with the end nearest a substituent.
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