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Chemistry 2100 Chapter 17
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Nomenclature IUPAC names for aldehydes
To name an aldehyde, change the suffix -e of the parent alkane to -al. Because the carbonyl group of an aldehyde can only be at the end of a parent chain and numbering must start with it as carbon-1, there is no need to use a number to locate the aldehyde group. For unsaturated aldehydes, indicate the presence of a carbon-carbon double bond by changing the ending of the parent alkane from -ane to -enal. Numbering the carbon chain begins with the aldehyde carbonyl carbon. Show the location of the carbon-carbon double bond by the number of its first carbon.
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Nomenclature The IUPAC system retains common names for some aldehydes, including these three.
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Nomenclature IUPAC names for ketones.
The parent alkane is the longest chain that contains the carbonyl group. Indicate the presence of the carbonyl group by changing the -ane of the parent alkane -one. Number the parent chain from the direction that gives the carbonyl carbon the smaller number. The IUPAC retains the common name acetone for 2-propanone.
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Nomenclature To name an aldehyde or ketone that also contains an -OH (hydroxyl) or -NH2 (amino) group: Number the parent chain to give the carbonyl carbon the lower number. Indicate an -OH substituent by hydroxy-, and an -NH2 substituent by amino-. Hydroxyl and amino substituents are numbered and alphabetized along with other substituents.
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Nomenclature Common names
The common name for an aldehyde is derived from the common name of the corresponding carboxylic acid. Drop the word "acid" and change the suffix -ic or -oic to -aldehyde. Name each alkyl or aryl group bonded to the carbonyl carbon as a separate word, followed by the word "ketone”. Alkyl or aryl groups are generally listed in order of increasing molecular weight.
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Physical Properties
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Physical Properties
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p. 461
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Preparations
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(1°) (2°)
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(1°) (2°)
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(1°) (2°)
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(1°) (2°)
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(1°) (2°)
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Reactions
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Z = C, H
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Z = C, H
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Z = C, H
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Z = C, H
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Z = C, H
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Z = C, H
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Z = C, H
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Z = C, H
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Z = X, O, N
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OH Z = X, O, N
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(xs)
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(xs)
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(xs)
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Cyclization
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1 6 6 2 5 5 3 1 4 4 1 4 3 2 3 2 5 6
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1 6 6 2 5 5 3 1 4 4 1 4 3 2 3 2 5 6
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1 6 6 2 5 5 3 1 4 4 1 4 3 2 3 2 5 6
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1 6 6 2 5 5 3 1 4 4 1 4 3 2 3 2 5 6
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1 6 6 2 5 5 3 1 4 4 1 4 3 2 3 2 5 6
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1 6 2 5 3 4 1 4 3 2 5 6
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1 6 6 6 4 2 5 5 5 3 1 4 4 1 3 4 2 3 2 3 2 1 5 6
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Reduction The carbonyl group of an aldehyde or ketone is reduced to an -CHOH group by hydrogen in the presence of a transition-metal catalyst. Reduction of an aldehyde gives a primary alcohol. Reduction a ketone gives a secondary alcohol.
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Reduction Reduction by NaBH4 does not affect a carbon-carbon double bond or an aromatic ring.
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Tollens Benedict
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Keto-Enol Tautomerism
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"enolizable"
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"enolizable"
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"enolizable"
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"enolizable"
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"enolizable"
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"enolizable"
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"enolizable"
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tautomers "enolizable"
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?
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?
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H
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H H H H
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H H H H H H
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H H H H H H
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H H H H H H
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enediol
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H enediol
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H enediol
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H enediol
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