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chapter_3_structure__stereochemistry_of_alkanes

chapter_3_structure__stereochemistry_of_alkanes - Chapter 3...

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Chapter 3 Structure and Stereochemistry of Alkanes
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Nomenclature (3-3) head2down Since the names of all organic compounds are based on alkanes, a brief summary of the rules of nomenclature is necessary. Table 3-2 gives you the names of the first 20 common straight chain alkanes (also see slide 79). 105 head2down Systematic Names or IUPAC names: IUPAC: International Union of Pure and Applied Chemistry
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head2down Rule 1 Find the longest continuous chain of C atoms and use the name of this chain as the base name of the compound. 106
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substituent (alkyl group) Name the alkyl (+ position) + the main chain 107 3-methylhexane or 4-methylhexane
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head2down If there is a choice between 2 or more chains of equal length, use the one with the greater # of substituents, it simplifies the name. 108
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head2down Rule 2 number the longest chain beginning with the end of the chain nearest a substituent. You always want the positions of the substituents to be as low as possible. 1 7 109 2 3 4 5 6 7 1 2 3 4 5 6 positions of substituents: 3, 4, 5, 6 = 18 positions of substituents: 2, 3, 4, 5 = 14
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Rule 3 Name the substituents attached to the longest chain as alkyl groups. Give the location of each alkyl group using the carbon # to which it is attached. The name and the position must be separated by a hyphen. 110 Use alphabetical order to name the substituents, not the number of their positions.
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Rule 4 (multiple groups) When 2 or more of the same substituents are present, use prefixes di (2), tri (3), tetra (4), … to avoid naming them more than once. (prefix such as di-, tri- tetra- etc are not used to determine the alphabetical order) 111 1 2 3 4 5 6 7 3-ethyl-2,4,5-trimethylheptane
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head2down Other common alkyl groups: 3 carbons 4 carbons CH 3 CH 2 CH 2 propyl CH 3 CH CH 3 isopropyl CH 3 CH 2 CH 2 CH 2 CH 3 CHCH 2 CH 3 112 CH 3 CH 2 CH CH 3 CH 3 C CH 3 CH 3 butyl isobutyl sec-butyl tert-butyl (t-butyl)
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head2down Classification carbon atoms C H H R C R R H C R R R primary (1 o ) secondary (2 o ) tertiary (3 o ) 113 carbon carbon carbon
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head2down Functional groups When functional groups are present, the same
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