Chemical Properties of Aldehydes and Ketones
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1 hemical Properties of Aldehydes and Ketones
2 hemical Properties of Aldehydes and Ketones xidation of Aldehydes Aldehydes are very easily oxidized to carboxylic acids. R [] R [] R primary alcohol aldehyde carboxylic acid From the standpoint of the organic component, an oxidation can involve the removal of hydrogen atoms R the addition of oxygen to the structure. xidation reagents: Mn4 -, r27 2-, Ag +, u 2+ Usually, the metal ion is reduced in the process.
3 hemical Properties of Aldehydes and Ketones xidation of Aldehydes xidation of Aldehydes forms the basis of two useful identification tests Tollen s Test: R + Ag R - + Ag R Benedict s Test: + 2 u R u 2
4 hemical Properties of Aldehydes and Ketones Benedict s Test for Aldehydes u 2+ u +
5 xidation of Aldehydes The degree of reduction varies with time and the concentration of the aldehyde.
6 hemical Properties of Aldehydes and Ketones Tollen s Test for Aldehydes Ag + Ag o
7 Ketones D NT undergo the same transformations with these oxidizing agents!!
8 hemical Properties of Aldehydes and Ketones Addition Reactions to arbon-xygen Double Bonds REVIEW:Reactions of arbon-arbon Double Bonds A A A B B B A and B can be the same or different atoms or groups of atoms. In some cases, the identity of A and B and the groups attached to the double bond influence the orientation of the addition.
9 hemical Properties of Aldehydes and Ketones Addition Reactions to arbon-xygen Double Bonds Reactions of the arbon-xygen double bond can be viewed in a similar manner. δ δ+ + Aδ+ B δ δ δ+ Aδ+ B δ A B A and B can be the same or different atoms or groups of atoms. The identity of A and B and the polar nature of the carbon-oxygen double bond influence the orientation of the addition.
10 Addition Reactions to arbon-xygen Double Bonds Reduction (ydrogenation) of Aldehydes and Ketones Break Bonds Form Bonds Aldehyde or Ketone Alcohol
11 Addition Reactions to arbon-xygen Double Bonds Reduction (ydrogenation) of Aldehydes and Ketones Ni (catalyst) ,3-dimethylbutanal 2,3-dimethyl-1-butanol 3 F F 2 Ni (catalyst) 3 F F 4-fluoro-2-pentanone 4-fluoro-2-pentanol
12 Addition Reactions to arbon-xygen Double Bonds ydrates, emiacetals, emiketals, Acetals, and Ketals δ δ+ X =, R δ+ δ X X If X=, --X is water; If X=R, --R is an alcohol.
13 Addition Reactions to arbon-xygen Double Bonds ydrates, emiacetals and emiketals???? R R Rʼ aldehyde hydrate ketone hydrate Rʼ R hemiacetal Rʼʼ R Rʼ hemiacetal (hemiketal)
14 acetone acetone hydrate Addition Reactions to arbon-xygen Double Bonds Addition of Water - ydrate Formation acetaldehyde acetaldehyde hydrate
15 Addition Reactions to arbon-xygen Double Bonds Addition of an Alcohol - emiacetal Formation propionaldehyde propionaldehyde methyl hemiacetal butanone butanone methyl hemiacetal
16 Addition of an Alcohol - emiacetal Formation
17 Addition of an Alcohol - emiacetal Formation
18 Further Reactions of emiacetals Reaction with an Alcohol - Acetal Formation ? propionaldehyde methyl hemiacetal propionaldehyde methyl acetal ? butanone butanone methyl hemiacetal methyl acetal
19 Further Reactions of emiacetals Reaction of a emiacetal with an Alcohol - Acetal Formation R Rʼ Rʼʼ R Rʼʼ Rʼ Rʼʼʼ Rʼʼ Rʼʼʼ R Rʼ R Rʼʼ Rʼ Note: Acetal formation from a hemiacetal is another example of an INTERMLEULAR DEYDRATIN or NDENSATIN reaction.
20 emiacetals and Acetals , + 3, , Aldehyde emiacetal Acetal Most hemiacetals are unstable and cannot be isolated. The equilibrium forming a hemiacetal lies far to the left, or to the reactant side of the reaction. The equilibrium forming an acetal from a hemiacetal lies far to the right, if excess alcohol is present.
21 emiacetals and Acetals Aldehyde emiacetal Acetal emiacetal and acetal formations are reversible reactions: In the presence of excess alcohol and acid, an aldehyde or ketone is converted into its corresponding acetal. In the presence of excess water and acid an acetal is converted into its parent aldehyde or ketone. Addition ondensation Elimination ydrolysis
22 Amylose Maltose Glucose Acetal linkages emiacetal linkage
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