Ch 16

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mckenzielarmstrong
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192412
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Ch 16
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2013-01-12 14:57:49
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Aldehydes Ketones Nucleophilic Additions Carbonyl Group
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Ch 16
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  1. A functional group consisting of a carbon atom doubly bonded to an oxygen atom, >C=O
    Carbonyl group
  2. A molecule containing a terminal carbonyl group, >C=O , that is attached to one hydrogen and one other carbon atom, with the general formula RCHO
    Aldehyde
  3. A molecule containing an internal carbonyl group, >C=O , that is attached to two other carbon atoms, with the general formula RCOR.
    Ketone
  4. A functional group consisting of a carbonyl group, >C=O, which is attached to an alkyl or aryl group, -C(=O)R; it is often added by reaction with a carboxylic acid derivative. Also called an alkanoyl group
    Acyl group
  5. The -CHO group. Also called a methanoyl group
    Formyl group
  6. The -COCH3 group. Also called an ethanoyl group
    Acetyl group
  7.  A reaction in which a nucleophile adds to a substrate containing a polar multiple bond between carbon and a heteroatom (such as a carbonyl or nitrile group); when a nucleophile attacks the δ+ carbon of a carbonyl group, an alkoxide anion intermediate is initially formed, which subsequently attacks an electrophile, such as H+ ; when an acid protonates a δ- carbonyl oxygen, an oxonium cation intermediate is initially formed, then the positively charged carbonyl carbon is attacked by a nucleophile.
    Nucleophilc addition
  8. A chemical species with an oxygen atom that bears a formal negative charge, such as a deprotonated alcohol, RO- , or a reaction intermediate formed after a nucleophile attacks a δ+ carbonyl carbon, R2 C(Nu)O- . Also called an oxide anion
    Oxide ion
  9. A chemical species with an oxygen atom that bears a formal negative charge, such as a deprotonated alcohol, RO- , or a reaction intermediate formed after a nucleophile attacks a δ+ carbonyl carbon, R2 C(Nu)O- . Also called an oxide anion
    Oxonium ion
  10. The product of the nucleophilic addition of one molecule of an alcohol to an aldehyde or ketone; the hemiacetal has one alkoxy group, -OR, and one hydroxyl group, -OH, on the former carbonyl carbon atom. This derivative of a ketone is also called a hemiketal.
    Hemiacetal
  11. The product of the nucleophilic addition of one molecule of water to an aldehyde; the hydrate has two hydroxyl groups, -OH, on the former carbonyl carbon atom; this product is a terminal gem-diol (1,1-diol)
    Aldehyde hydrate
  12. The product of the nucleophilic addition of two molecules of an alcohol to an aldehyde or ketone, with loss of one molecule of water; the acetal has two alkoxy groups, -OR, on the former carbonyl carbon atom. This derivative of a ketone is also called a ketal.
    Acetal
  13. A group that is introduced into a molecule to protect a sensitive group, while the reaction is carried out at some other location in the molecule; the protecting group is later removed in a subsequent reaction
    Protecting group
  14.  A molecule containing a sulfhydryl (mercapto) group, -SH, which is the sulfur analogue of an alcohol. Also called a mercaptan.
    Thiol
  15. A derivative of an aldehyde or ketone having two alkylthiol groups, -SR, in place of the carbonyl group, which is derived by adding two molar equivalents of a thiol.
    Thioacetal
  16. A finely divided, hydrogen-bearing form of nickel made by treating a nickel-aluminum alloy with strong sodium hydroxide; the aluminum in the alloy reacts to form hydrogen, leaving a finely divided nickel powder saturated with hydrogen. Raney nickel desulfurization of thioacetals will leave a reduced methylene group
    Raney nickel
  17. A compound with a carbon-nitrogen double bond, R2C=NR', formed by the reaction of a ketone or aldehyde with a primary amine; a substituted imine is often called a Schiff base.
    Imine
  18. 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
  19. A compound containing the -C=N-OH group, formed by the reaction of an aldehyde or ketone with hydroxylamine, NH2OH
    Oxime
  20. A compound containing the -C=N-NH2 group, formed by the reaction of an aldehyde or ketone with hydrazine, NH2 NH2
    Hydrazone
  21. A hydrazone formed by the reaction of an aldehyde or ketone with 2,4-dinitrophenylhydrazine
    2,4-DNP derivative
  22. A compound containing the -C=N-NH-CONH2 group, formed by the reaction of an aldehyde or ketone with semicarbazide, H2NCONHNH2
    Semicarbazone
  23. A compound with a hydroxyl group and a cyano group on the same carbon atom, R2C(OH)(CN), derived by adding HCN to an aldehyde or ketone.
    Cyanohydrin
  24. An electrically neutral molecule that has a negative carbon, with a lone pair of electrons, adjacent to a positive heteroatom.
    Ylide
  25. Reaction of an aldehyde or ketone with a phosphorus ylide to form an alkene.
    Witting rxn
  26. A test for aldehydes and α-hydroxy ketones. Adding the Tollens reagent, Ag(NH3)2OH, which is a silver-ammonia complex, will give a carboxylate salt and a silver mirror on the inside of a glass container.
    Tollens test

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