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The carbonyl group (C=O) is found in aldehydes, ketones, and many other organic functional groups. The carbon and oxygen in the carbonyl group are sp2-hybridized,

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Presentation on theme: "The carbonyl group (C=O) is found in aldehydes, ketones, and many other organic functional groups. The carbon and oxygen in the carbonyl group are sp2-hybridized,"— Presentation transcript:

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2 The carbonyl group (C=O) is found in aldehydes, ketones, and many other organic functional groups. The carbon and oxygen in the carbonyl group are sp2-hybridized, with bond angles of 120°.

3 In ketones, two carbon groups are attached to the carbonyl carbon, while in aldehydes at least one hydrogen is attached to the carbon

4 Aldehydes are named by replacing the terminal -e of the corresponding alkane name with –al The parent chain must contain the  CHO group The  CHO carbon is numbered possible minimum number.

5 IIUPAC LLONGEST CHAIN WITH ALDEHYDE DDROP “e” AND ADD “-al” AALDEYHYDE TAKES PRECEDENCE OVER ALL OTHER GROUPS SO FAR. EEXAMPLES

6 Naming Ketones Replace the terminal -e of the alkane name with –one Parent chain is the longest one that contains the ketone group Numbering begins at the end nearer the carbonyl carbon

7 Ketones with Common Names IUPAC retains well-used but unsystematic names for a few ketones

8 Oxidation of Primary Alcohols The aldehyde can be oxidized in a second step [O] represent an oxidation

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11  Requires less vigorous oxidation conditions.  We can try to remove the aldehyde from the reaction medium as quickly as it is formed  Generally, the aldehyde has a lower boiling point than either the corresponding alcohol or carboxylic acid  We can also try to find a milder oxidizing agent.

12 This reaction is generally done by passing the vapors of the alcohol through a tube furnace in a stream of inert carrier gas. This is not a practical laboratory method -- it is better suited to industrial processes. The reaction stops at the aldehyde stage -- no more removal of hydrogen can take place.

13 Oxidation of Primary Alcohols with K 2 Cr 2 O 7 This reaction can also be done using CrO 3 (chromic oxide) in sulfuric acid. The aldehyde is distilled away from the reaction vessel as quickly as it is formed. If the aldehyde is not removed, it will suffer a second oxidation, and the product will be the carboxylic acid.

14  The acidic conditions keep the chromium in the Cr 2 O 7 2- state.  Potassium dichromate is not as powerful an oxidizing agent as is potassium permanganate  Sodium dichromate can be substituted for potassium dichromate -- it makes no difference.  There is a color change during the reaction. The orange color of the dichromate changes to the green of Cr 3+ ion.  This is not the world’s greatest way to prepare an aldehyde!

15 Sarett Oxidation

16 “PCC” Oxidation

17 CHANGE OF GEARS: Aldehydes can be oxidized to carboxylic acids. This oxidation can take place under very mild oxidizing conditions. Aldehydes can be oxidized with such weak oxidizing agents as metal cations, especially: Ag + Cu 2+


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