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Aldehydes and Ketones

Topic Review on "Title":

Background for Aldehydes and Ketones
An aldehyde contains at least one hydrogen attached to the C of a C=O (carbonyl group).  A ketone contains two alkyl groups attached to the C of the carbonyl group. The carbon in the carbonyl is sp2 hybridized, has a bond angle of 120o, and is trigonal planar. Aldehydes and ketones have dipole-dipole attractions between molecules, and no hydrogen bonding between molecules.  These compounds can hydrogen bond with compounds have O-H or N-H bonds.  The melting points and boiling points of aldehydes and ketones are between alkanes and alcohols.  Small aldehydes and ketones are soluble in water.  Some compounds are very flammable.

Uses of Aldehydes and Ketones
Formaldehyde can be used to preserve dead animals.  Acetone is a common fingernail polish remover and is a solvent.  Acetone is very flammable. 2-Butanone (MEK, methyl ethyl ketone) is used as a solvent and paint stripper.  2-Butanone is very flammable.  Benzaldehyde is an almond extract. (-)-Carvone is used as spearmint flavoring.  (+)-Carvone is used as caraway seed flavoring.  Vanillin is the vanilla flavoring.

IUPAC Nomenclature for Aldehydes and Ketones
For the IUPAC nomenclature, the longest continuous carbon chain is the parent compound.  Number the chain so that the C-O or bond has the lowest possible number.  Give the location of the C-O bond with a number for ketones.  From the alkyl prefixes, use Aanal@ for aldehydes, and Aanone@ for ketones.  Name and number substituents.

Common Nomenclature for Aldehydes and Ketones
A ketone is named as an alkyl alkyl ketone. Use the common prefixes (n, iso, sec, tert, neo).  Alphabetize the groups.

Synthesis of Aldehydes and Ketones
Zero degree and primary alcohols are oxidized with pyridinium chlorochromate to form aldehydes. Secondary alcohols are oxidized with sodium dichromate, potassium dichromate, potassium permanganate, sodium hypochlorite, nitric acid, chromium trioxide, or pyridinium chlorochromate to ketones. Benzene reacts with aluminum chloride and an acid halide to form a ketone. Alkenes are oxidized to aldehydes and / or ketones with ozone. Acid chlorides are reduced to aldehydes with lithium aluminum tri(t-butoxy) hydride. Acid chlorides react with dialkyl lithium cuprates to yield ketones.

Reactions of Aldehydes and Ketones
Organolithium or Grignard reagents react with aldehydes or ketones, followed by acidification, produce alcohols.  Aldehydes and ketones are reduced to alcohols with hydrogen and Raney nickel, lithium aluminum hydride, or sodium borohydride. Aldehydes and ketones are reduced to alkanes with amalgamated zinc (zinc treated with mercury) and hydrochloric acid in the Clemmenson reduction. Aldehydes and ketones are reduced to alkanes with hydrazine and potassium hydroxide in the Wolff-Kishner reduction. Aldehydes and ketones react with ammonia derivatives, in the presence of acid, to form imine derivatives. Aldehydes are oxidized with sodium dichromate, potassium dichromate, potassium permanganate, sodium hypochlorite, nitric acid, or chromium trioxide to form carboxylic acids.


Rapid Study Kit for "Title":
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"Title" Tutorial Summary :
The background information of aldehydes and ketones are discussed by the structure, shape, properties, and uses.  Aldehydes and ketones are named by the IUPAC and common rules.  Primary alcohols are oxidized to aldehydes.  Second alcohols are oxidized to ketones.  The Friedel-Craft acylation of benzene produces aryl ketones.  The ozonolysis of alkenes give aldehydes and / or ketones.  Acid halides are reduced to aldehydes.  Ketones are formed from the reaction of acid halides with dialkyl lithium cuprates.  Aldehydes and ketones react with organolithiums or with Grignard reagents to give alcohols.  Reduction of aldehydes and ketones give alcohols or alkanes, depending upon the reagent.  Primary amines or their derivatives react with aldehydes and ketones to give imines.  The oxidation of aldehydes produce carboxylic acids.

Tutorial Features:

This tutorial provides the comprehensive coverage of the chapter with easy introduction and simple illustration. It features:

  • Concept map showing interconnections of new concepts in this tutorial and those previously introduced.
  • Definition slides introduce terms as they are needed.
  • Visual representation of concepts.
  • Use of colors to emphasis points.
  • Outline of chemical structure, shape, properties, and uses.
  • Easy-to-follow animations of stated rules of nomenclature.
  • Detailed stepwise explanations and animations of reactions and mechanisms.
  • Examples worked out step-by-step throughout the tutorial.
  • A concise summary is given at the conclusion of the tutorial.

"Title" Topic List:

Background Information for Aldehydes and Ketones

  • Structure
  • Shape
  • Properties
  • Uses

Nomenclature of Aldehydes and Ketones

  • IUPAC
  • Common

Synthesis of Aldehydes and Ketones

  • Oxidation of Alcohols
  • Friedel-Craft Acylation of Benzene
  • Ozonolysis of Alkenes
  • From Acid Halides

Reactions of Aldehydes and Ketones

  • Reaction with Organometallics
  • Reduction to Alcohols
  • Reduction to Alkanes
  • Formation of Imine Derivatives
  • Oxidation of Aldehydes to Carboxylic Acids


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