Ch 19

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mckenzielarmstrong
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192680
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Ch 19
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2013-01-13 21:27:01
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Condensation Conjugate Addition Reactions Carbonyl Compounds More Chemistry Enolates
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Ch 19
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  1. Compounds that have two carbonyl groups, >C=O, that are separated by one carbon atom, with the general formula, RCOCH2COR.
    β-Dicarbonyl
  2. A reaction that joins two molecules, with the loss of water or an alcohol. Also called a dehydration synthesis reaction when water is lost
    Condensation rxn
  3. Base-catalyzed condensation of an ester containing two α-hydrogens with a molecule of the same ester to produce a β-keto ester; the overall reaction involves loss of an α-hydrogen from one ester and loss of an ethoxide ion from the other ester. Also called acetoacetic ester condensation
    Claisen condensation
  4. An intramolecular Claisen condensation that forms a five- or six-membered ring, which is a base-catalyzed cyclization of a dicarboxylic acid ester to produce a cyclic β-ketoester
    Dieckmann condensation
  5. A Claisen condensation between an ester with no α-hydrogens, and a different ester with two or more α-hydrogens
    Crossed claisen condensation
  6. Nucleophilic substitution reactions between a ketone enolate ion and an ester, to produce a β-dicarbonyl compound
    Acylation of ketone enolates
  7. A compound that is both an aldehyde (or ketone) and an alcohol; most aldols are β-hydroxy aldehydes or β-hydroxy ketones
    Aldol
  8. An acid- or base-catalyzed nucleophilic addition of the enolate of an aldehyde (or ketone) to the carbonyl carbon atom of an aldehyde (or ketone) to produce an aldol (β-hydroxy aldehyde or β-hydroxy ketone)
    Aldol rxn
  9. An aldol addition reaction followed by dehydration to produce an α,β-unsaturated aldehyde or α,β-unsaturated ketone, which is catalyzed by an acid, or by a base with heat.
    Aldol condensation
  10. A base-catalyzed conversion of an aldol into an aldehyde (and/or ketone)
    Retro-aldol rxn
  11. An alkene aldehyde, which is usually conjugated, such as an α,β-unsaturated aldehyde, R2C=CHCHO
    Enal
  12. An alkene ketone, which is usually conjugated, such as an α,β-unsaturated ketone, R2C=CHCOR
    Enone
  13. An aldol addition reaction between two different aldehydes or ketones; this reaction is practical only when one reactant has no α hydrogen
    Crossed aldol rxn
  14. A crossed aldol addition reaction followed by dehydration to produce an α,β-unsaturated aldehyde or α,β-unsaturated ketone; only practical when one reactant has no α hydrogen.
    Crossed aldol condensation
  15. A base-catalyzed aldol condensation of an aromatic aldehyde with a ketone (or aliphatic aldehyde) to produce an α,β-unsaturated ketone (or α,β-unsaturated aldehyde).
    Claisen-Schmidt condensation
  16.  The most stable enolate formed from an unsymmetrical ketone, which has the more highly substituted double bond; it is favored by use of a protic solvent with a base that is weaker than the enolate ion, such as hydroxide ion or alkoxide ion, so that equilibrium can be established
    Thermodynamic enolate
  17. The enolate formed fastest from an unsymmetrical ketone, which usually has the least substituted double bond; it is favored by use of a very strong, sterically hindered base, such as LDA (lithium diisopropylamide), in an aprotic solvent that is unreactive with bases, such as an ether like THF (tetrahydrofuran) or DME (dimethoxyethane).
    Kinetic enolate
  18. A very strong, sterically hindered base, ( i-C3H7 )2 N‾ Li+ , whose conjugate acid has pKa = 38. Abbreviated LDA
    Lithium diisopropylamide
  19. A crossed aldol reaction is forced to occur between a ketone enolate and an aldehyde by first deprotonating the ketone with LDA (lithium diisopropylamide), then slowly adding the aldehyde; if the ketone is unsymmetrical, then it will be selectively deprotonated by LDA at the less substituted α carbon to form the kinetic enolate.
    Directed aldol rxn
  20. An intramolecular aldol condensation of a dicarbonyl compound, usually a keto aldehyde, to form a five- or six-membered ring
    Aldol cyclization
  21.  An addition reaction in which two groups add to adjacent atoms in a conjugated system, which is fast and under kinetic control; in α,β-unsaturated carbonyl compounds, a nucleophile adds to the carbonyl carbon and the carbonyl oxygen is protonated
    1,2 (simple) addition
  22. An addition reaction in which two groups add to atoms that bear a 1,4-relationship in a conjugated system, which is energetically favored and under thermodynamic control; in α,β-unsaturated carbonyl compounds, a nucleophile adds to the β carbon and the carbonyl oxygen is protonated.
    1,4 (conjugate) addition
  23. Base-promoted conjugate addition (1,4-addition) of a resonance stabilized carbanion nucleophile, such as a deprotonated active hydrogen compound (Michael donor), to an electrophilic conjugated double bond, such as an α,β-unsaturated carbonyl compound (Michael acceptor)
    Michael addition
  24. A vinyl amine, usually generated by the acid-catalyzed reaction of a secondary amine with an aldehyde or ketone, which has the general formula: R2C=C(NR2)R.
    Enamine
  25. Formation of a new six-membered ring, an α,β-unsaturated cyclic ketone, by the Michael addition of a cyclohexanone derivative to a methyl vinyl ketone derivative, followed by an intramolecular aldol condensation
    Robinson annulation
  26. The reaction of the enol form of a carbonyl compound with the imine derived from formaldehyde and a primary or secondary amine to produce a β-aminoalkyl carbonyl compound
    Mannich rxn

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