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30 Cards in this Set
- Front
- Back
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What is the difference between and aldehyde and a ketone?
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A ketone is carbonyl group in the center of the molecule while the aldehyde is the carbonyl at the end of molecule with a hydrogen attached to it
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What is unique about carbonyl groups in terms of nucleophilicity and electrophilicity
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A crabonyl group can act as both a nuleophile and an electrophile
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Naming aldehydes
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If you have an aldehyde on a chain, all you need to do is add the suffix -al to the end of the chain
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Naming aldehydes that are attached to rings.
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If you have an aldehyde that is attached to a ring, you add the suffix -carbaldehyde to the end of the name
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Naming ketones
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If you have a ketone, all you do is add the suffix -one to the end of the name. However, you must make sure to specify the number of the carbon that is attached to the ketone
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Naming ketones that are not the highest ranking functional group
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If you have a ketone that is outranked by another functional group, you add the suffix -oxo to the end of the name.
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Structure of Formaldehyde and Acetylaldehyde
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The former is methanal which is a carbonyl group that has two Hs attached to the carbon. The latter of ethanal has one carbon attached to the carbonyl and one attached to the H
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Physical Properties of aldehydes and ketone
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Given the fact that the carbonyl group has a dipole, the molecule have greater dipole interaction and thus have a higher boiling point.
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Three ways to make an aldehyde or ketone
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1) PCC will oxidize a primary alcohol to an aldehyde. Dichromate will turn a secondary alcohol into a ketone
2) Ozonolysis will cut the double bond and give either a ketone or an aldehyde 3) Freidel Craft Acylation |
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Keton Enol Tautomerization
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A ketone and and Enol will shift back and forth with the reaction lying heavily to the side of the ketone since it is much more stable
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Michael Additions
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In this reaction, the beta hydrogen of a dicarbonyl will attach and to one of the carbons that had a double bonded oxygen. This reaction will take place upon exposure to a base
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Water + carbonyl
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The water will attack the carbon and lead to the formation of an OH group and the removal of the double bond. This will lead to the a negative charge on the oxygen which will then get protonated which will lead to the formation of two hydroxy groups
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How would you recognize a heiacetal or hemiketal?
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Each has a hydroxy group attached to it
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How do you form ketals or acetals?
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They are formed through the exposure of a ketone or aldehyde to an alcohol
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Ketal Structure
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http://upload.wikimedia.org/wikipedia/commons/2/2a/Ketal_formation.png
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Acetal Structure
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http://upload.wikimedia.org/wikipedia/commons/e/ef/Acetal_formation_2.png
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Carbonyl + CN
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The CN will attack the carbon of the carbonyl and attach. The double bond will be removed leading to a negative O. The negative O will then get protonted. The result will be the addition of a CN group and the formation of a hydroxy group. The name of this compound is CYANOHYDRIN
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Imine
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A compound with a nitrogen atom that is double bonded to a carbon
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Carbonyl + NH3
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The NH3 will attack the carbon on the carbonyl group and attach. This will remove the double bond to the oxygen making it negative. The negative O will be protonated two times making it water which will dissociate from the molecule. Given the the water molecule has fallen off, a double bond will form between the carbon and the NH2 group. A base it then added which will remove the 2 Hs from the N.
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General Pattern the Should Emerge
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It should become clear that when you see a carbonyl group it will be an electrophile which will get attacked by the nucleophile. This attach will then remove the double bond to the oxygen which will become negative and may get protonated.
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What is an aldol?
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An aldol is a molecule that has both an ALDEHYDE group and an ALCOHOL group.
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Aldol Condensation
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In the presence of a base, carbonyl groups will act as both nucleophiles and electrophiles. In this case, the double bond of a carbonyl group will act a nucleophile and attack the positive charged carbon of another carbonyl group. As before, the groups will attach and one will lose its double bond. Also as before, when one group loses its double bond the O will become negative and get protonated and create and alcohol. At the end of the reaction you have a molecule with an alcohol group and a aldehyde (since the carbonyl is at the end of the molecule).
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What does a wittig reaction do?
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The wittig reaction will replace the C=O bond on the carbonyl group an replace it with a C=C group making it an alkene. The wittig reaction will turn a carbonyl into a an alkene
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Zwitteron
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A molecule that has both a positive and negative charge. This is different from a dipole because a dipole has a region of positive and negative charge where here there is an actual charge.
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Wittig Reaction
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The negative charge of a zwitteron will attack the positive dipole of the carbonyl group. When this occurs the Oxygen molecule will be removes and a carbon will placed in its stead
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What will KMnO4, CrO3/Ag2O do to an aldehyde?
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They oxidize and thus convert it into a carboxylic acid.
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LAH or NaBH4 + Carbonyl
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They will remove the double bond and turn the carbonyl into an alcohol
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Wolf Kishner Reduction
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This will turn a carbonyl into an alkane. H2NNH2 will displace the O atom. Then treating it with base will remove the double bonded NNH2 group to give an alkane
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Clemmensen Reduction
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Hg(Zn)/HCl will reduce a double bond of a carbonyl group and turn it into an alkane
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What are the two ways to turn a carbonyl group (which includes aldehydes and Ketones) into an alkane?
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1) Hg(Zn)/HCl
2) H2NNH2 then Base |
