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

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Unformatted text preview: Chapter 3 Structure and Stereochemistry of Alkanes Chapter 32 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 CC H H H CH H H H H Isobutane, C 4 H 10 Chapter 33 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 Chapter 34 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 CC H H CH 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 Chapter 35 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 CHCH 2 CH 2 CH 3 CHCH 2 CH 3 H 3 C H 3 C 3-3B IUPAC Names The systematic way to name all organic compounds. Chapter 36 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 CH 3 CH CH 2 CH 3 CH 2 CH 2 CH CH 3 CH 3 Chapter 37 Name Alkyl (Substituent) Groups •C H 3-, methyl •C H 3 CH 2-, ethyl •C H 3 CH 2 CH 2-, n-propyl •C H 3 CH 2 CH 2 CH 2-, n-butyl CH 3 CHCH 2 CH 3 sec- butyl CH 3 CH CH 3 CH 2 isobutyl CH 3 CHCH 3 isopropyl C H 3 C CH 3 CH 3 tert-butyl Chapter 38 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 Chapter 39 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 carbonA secondary carbon Chapter 310 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 carbonA tertiary carbon isobutyl tert-butyl Chapter 311 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 Chapter 312 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 Chapter 313 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. (3) Name the substituent groups attached to the longest chain as alkyl groups. Also state the location of each alkyl group according to its numbered carbon on the main chain. (4) When two or more substituents are present, list them in...
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This note was uploaded on 04/08/2008 for the course CHE 201 taught by Professor Bong during the Spring '08 term at SUNY Buffalo.

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

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