Ch 17

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mckenzielarmstrong
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192675
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Ch 17
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2013-01-13 21:16:44
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Carboxylic Acids Derivatives
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Ch 17
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  1. A functional group where a terminal carbon is part of a carbonyl group, >C=O, and is bound to a hydroxyl group, -OH, to form a carboxylic acid, RCOOH
    Carboxyl Group
  2. A compound containing an acyl group, (R-C=O)- ; it is usually derived from a carboxylic acid, such as an ester, acyl halide, amide, or carboxylic acid anhydride.
    Acyl compound
  3. Molecule containing a carbonyl group, >C=O , that is attached to a hydroxyl group, -OH , which is called a carboxyl group, -COOH, with the general formula RCOOH.
    Carboxylic acid
  4.  Compound that yields a carboxylic acid on hydrolysis, such as esters, acid anhydrides, acyl chlorides, amides, and nitriles
    Carboxylic acid derivative
  5. The anion resulting from deprotonation of a carboxylic acid, RCOO‾ ; it is isolated as the salt of the carboxylic acid.
    Carboxylate ion
  6. Compound with two carboxyl groups, -COOH. Also called alkanedioic acid
    Dicarboxylic acid
  7. A molecule containing a carbonyl group, >C=O , that is attached to an alcohol group, -OR' , with the general formula RCOOR' , often formed by the reaction of a carboxylic acid and an alcohol with loss of water. Also called carboxylic ester.
    Ester
  8. An activated carboxylic acid derivative formed from two acid molecules with loss of a molecule of water; a mixed anhydride is derived from two different carboxylic acid molecules
    Carboxylic acid anhydride
  9. An activated carboxylic acid derivative in which the hydroxyl group of the acid is replaced by a chlorine atom, RCOCl
    Acyl chloride
  10. A molecule containing a carbonyl group, >C=O , that is attached to an amino group, -NR2 , with the general formula RCONR'2 (R may be hydrogen); often formed by the reaction of a carboxylic acid and an amine, with loss of water
    Amide
  11. A molecule containing a cyano group, -C≡N , with the general formula RCN
    Nitrile
  12.  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
  13. A reaction in which a carboxylic acid group is introduced in a substrate, such as the addition of CO2 to a Grignard reagent: RMgX + CO2 → RCOOH. Also called carbonation.
    Carboxylation
  14. Two-stage substitution reaction, in which one type of carboxylic acid derivative is converted into another, which involves addition and elimination reactions; in the addition stage, the nucleophile adds to the carbon that bears the leaving group; in the elimination stage, the leaving group is expelled
    Nucleophilic acyl substitution
  15. Two-stage mechanism for a nucleophilic addition-elimination reaction; in the addition stage, the nucleophile adds to the carbon that bears the leaving group, then in the elimination stage, the leaving group is expelled
    Nucleophilic addition-elimination mechanism
  16. The substituent that departs with a lone pair of electrons from the substrate in a nucleophilic substitution reaction. The best leaving groups depart as stable weak bases.
    Leaving group
  17. The acid-catalyzed reaction of a carboxylic acid with an alcohol to give a carboxylic ester and water
    Fischer esterification
  18. Substitution of one alkoxy group for another in an ester, which can take place under either acidic or basic conditions
    Transesterification
  19. Basic hydrolysis of an ester into an alcohol and a carboxylate salt
    Saponification
  20. A cyclic ester; δ-hydroxyacids can undergo an intramolecular esterification to produce δ-lactones, which contain a six-membered ring
    Lactone
  21. A compound with two carbonyl groups bound to the same nitrogen atom, RCONHCOR'
    Imide
  22. A cyclic amide; δ-aminoacid can undergo an intramolecular condensation to produce δ-lactams, which contain a six-membered ring
    Lactam
  23. The inorganic, weak diprotic acid, HOC(=O)OH, or H2CO3 ; its acid dissociation constants are pKa1 = 6.35 and pKa2 = 10.2 ; it is formed by the equilibrium reaction between water and carbon dioxide: H2O + CO2 ↔ H2CO3
    Carbonic acid
  24. The simplest acid chloride, ClCOCl , that is formally derived from carbonic acid. Also called phosgene
    Carbonyl dichloride
  25.  A diester of carbonic acid, ROC(=O)OR'
    Carbonate ester
  26. An amide of carbonic acid, HOC(=O)NH2
    Carbamic acid
  27. An ester, ROC(=O)NHR', that is formed by the reaction between an alkyl chloroformate, ROC(=O)Cl, and an amine, R'NH2 ; it can also be formed by the reaction between an alcohol, ROH, and an isocyanate, R'-N=C=O ; carbamate derivatives formed by reacting an alcohol with α-naphthyl isocyanate are crystalline solids with sharp melting points. Also called urethane
    Carbamate
  28. An organic compound that is the diamide of carbonic acid, H2NCONH2 , with two amine groups, -NH2 , joined to a carbonyl group, >C=O . Also called carbamide
    urea
  29. (1) A chemical reaction that releases carbon dioxide. (2) A reaction whereby a carboxylic acid, RCOOH, loses a carboxyl group, -COOH, as carbon dioxide, O=C=O.
    Decarboxylation

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