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By: Kendra & Ashley
General Structure
• Carbon double bonded to oxygen with two hydrocarbon groups (alkyl groups)
• Ketones never have a hydrogen atom attached to the carbonyl group R C
O
R'ketone
: :
http://en.wikipedia.org/wiki/File:Acetone-3D-balls.png
IUPAC Names for Ketones
the -e ending of the parent alkane is replaced with the -one suffix of the ketone family
The location of the carbonyl carbon is indicated with a number.
The longest carbon chain is numbered to give the carbonyl carbon the lowest possible number.
The alkyl groups are listed alphabetically or in order of increasing size. : :
R C
O
R'
alkyl alkyl ketonewww.chemrat.com/ChemHog2/Organic%20Chem
Common Names
CH3 C
O
CH3
CCH3
O
C
Oacetone acetophenone
benzophenone
http://www.cartage.org.lb/en/themes/sciences/chemistry/organicchemistry/Families/Somefamilies/Ketones/Ketones.htm
CH3CCH2CH3
OCH3CHCCHCH3
O
Cl CH3
C CH2CH2CH3
O
1 2 3 4
1 2 4 5
OH3C
1 2 3 4
2-butanone 2-chloro-4-methyl-3-pentanone 1-phenyl-1-butanone
1
23
4
4-methyl-2-cyclohexen-1-one
Examples
www.chemrat.com/ChemHog2/Organic%20Chem
Examples
CH3CH2CCH3
O
CH3CH2CCH2CH3
O
2-butanone 3-pentanone
CH3CCH2CH2CH3
O
2-pentanone
3-methyl-2-butanone
CH3 C
O
CH
CH3
CH3
O
Br
3-bromocyclohexanone
CH3 C
O
CH
CH3
CH2OH
4-hydroxy-3-methyl-2-butanone
ExamplesExamples
www.austincc.edu/cuzomba/
Benedict's test
The Benedict's test differentiates aldehydes and ketones. Aldehydes can be oxidized by Cu2+ in the presence of a strong base to form carbonic acids. Ketones cannot be oxidized by this reaction.
When the Cu2+ oxidizes the aldehydes it is reduced to Cu+, and forms the compound Cu2O, which is a reddish precipitate. That is how you know you have an aldehyde. If it doesn’t turn red, you know you have a ketone.
http://www.chemguide.co.uk/organicprops/carbonyls/addelim.html#top
Tollen’s test
The Tollen’s test, is a basic solution of Ag(NH3)+. The Silver (I) cation is reduced (gains one electron) at the same time the aldehyde is oxidized.
This produces metallic silver (Ag0), which often forms a shiny “mirror” look. Thus Tollens’ reagent can be used to detect the presence of an aldehyde functional group – if a mirror forms then the compound tested is an aldehyde. If the test fails, then the compound is a ketone.
http://www.chemguide.co.uk/organicprops/carbonyls/addelim.html#top
Hydrazine test
Hydrazine test can be used to detect ketones. When treated with 2,4 dinitrophenyl hydrazine, ketones are converted to their respective hydrazones, due to the presence of the carbonyl group, and an yellow or orange precipitate is observed.
Hydrazones have a sharp melting point, and can be used to detect the original ketone.
http://www.chemguide.co.uk/organicprops/carbonyls/addelim.html#top
Everyday Uses
• Carvone = spearmint flavouring
• Acetone = Nail polish remover, paint thinner, & cleaning solvents
• Demascone = berry flavouring
• Octanone = mushroom flavouring
• Benzophenone = perfume & sunscreen
http://highered.mcgraw-hill.com/sites/dl/free/0073402621/825918/Chapter13.pdf
http://www.google.ca/imgres?q=nail+polish+remover
http://www.google.ca/imgres?q=vanilla