2444-093011

2444-093011 - QUIZ Average Stnd Dev 14.6 25 5.8 THREE 2...

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QUIZ THREE Average 14.6 / 25 Stnd. Dev. 5.8
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Aldehyde Nomenclature 2 • An aldehyde is the name given to a molecule with one alkyl group and one hydrogen atom attached to a carbonyl (see 12 ), but the functional group is still the carbonyl unit , C=O. • The suffix for aldehydes derives from the first two letters of al dehyde, -al. • The carbonyl carbon takes priority, must be part of the longest continuous chain, and is given the lowest possible number. In all cases , the number of the carbonyl carbon will be 1 since all aldehydes have a hydrogen atom attached to the carbonyl unit. Therefore, the number is omitted from the name. • A specific example of an aldehyde is 13 , nonanal . • Note the use of nonan- and –al, where the former is derived from the saturated nonane skeleton. The –e is dropped and replaced with –al. • Substituents attached to the aldehyde chain are named in the usual manner, with the carbonyl carbon always numbered 1. • Aldehyde 14 has a 10-carbon alkane chain so it is a decanal. Using the carbonyl carbon as C1, there is a 1-methylpropyl group at C3 and a methyl group at C5. • The name is 5-methyl-3-(1-methylpropyl)decanal (the decanal chain is marked in blue ). R O H C 5 H 11 H O CH 3 R—CHO O H 12 14 13
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Aldehyde Nomenclature 3 • The carbonyl of an aldehyde has a higher priority than the C=C of an alkene or the C ! C of an alkyne. Compound 15 has an ten-carbon chain that includes the C=C and C=O units, but is also has a 14-carbon chain that includes only the C=C unit. The nomenclature rules demand that the longest chain contain both functional groups , and 15 has an en-al backbone, so the aldehyde suffix is used. • Compound 15 is a dec-3-enal (the longest chain is marked in blue ) with a dimethyl unit at C7 and a hexyl group at C3. Note that the alkene is a Z- alkene, so 15 is 7,7-dimethyl- 3-hexyldec-3Z-enal. • In 16 there is 12-carbon chain that includes only the C ! C unit, but the longest chain that includes both C ! C and C=O is marked in blue . Since the aldehyde unit is higher in priority, 16 is a nonynal. • There is a butyl group at C4 and a methyl group at C3, relative to the aldehyde carbonyl, so 16 is 2-butyl-3-methylnon-8-ynal . • Note that the aldehyde unit is drawn using a shorthand version –CHO for both 15 and 16. CHO CHO 15 16
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Aldehyde Nomenclature 4 • When the aldehyde unit (-CHO) is attached to a ring, a major modification in the name is required. • Aldehyde 17 is not named cyclohexanal. • This name makes no sense since an aldehyde must have the
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2444-093011 - QUIZ Average Stnd Dev 14.6 25 5.8 THREE 2...

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