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PMP 102 Drugs & Medicines > Carboxylic acids and derivatives > Flashcards

Carboxylic acids and derivatives Flashcards

1
Q

Carboxyl group

A
  • Combination of a C=O and a -OH on the same C
  • Weak acids compared with the mineral acids,
    but they are more acidic than alcohols or phenols.
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2
Q

Aliphatic acid

A
  • Alkyl group bonded to the carboxyl
    group
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3
Q

Aromatic acid

A
  • Aryl group bonded to the carboxyl group
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4
Q

Carboxylic acid angles

A
  • Sp2 hybrid carbonyl C atom is planar, with nearly trigonal bond angles
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5
Q

Carboxylic acid in drugs

A
  • Make carboxylic acid into a salt to increase the solubility
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6
Q

Lactones

A
  • Cyclical carboxylic acid
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7
Q

Lactams

A
  • Cyclical amides
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8
Q

Carboxylic acid + amide

A
  • Ammonium carboxylate salt
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9
Q

Acid Halides

A
  • Halide ions are excellent leaving group for nucleophile acyl substitution
  • Acid chloride active form of carboxylic acid
  • Carbonyl O and Cl makes it electrophilic
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10
Q

Acid Anhydrides

A
  • Anhydride forms into two molecules of acid
  • Activated form of a carboxylic acid. Carboxylate group leaves (good leaving group)
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11
Q

Synthesis of Carboxylic acids

A
  • From alkyl halide Halide to a carboxylic acid conversion with an additional carbon atom with Grignard reagents
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12
Q

Formation and hydrolysis of nitriles

A

Limited to halides and tosylates (OTs)
that are good SN2 electrophiles

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13
Q

Carboxylate anion

A
  • Weak base - can act as a nucleophile
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14
Q

Ester formation

A

Prepared by reacting alkyl halide and a carboxylate

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15
Q

Nucleophilic Acyl Substitution

A

One nucleophile replaces another on
the acyl (C=O) carbon atom

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16
Q

Basic conditions hydrolysis of ester
Nucleophilic Acyl Substitution

A
  • Hydroxide ion (strong nucleophile) adds to C=O, forming tetrahedral intermediate
  • An alkoxide ion leaves, regenerating the C =O double bond and stabilises itself
  • A fast, exothermic proton transfer drives the reaction to completion
17
Q

Nucleophilic Acyl Substitution Acid conditions Fisher Esterification

A
  • Acid-catalysed addition of the alcohol to the carbonyl group
  • Acid-catalysed dehydration
  • Methods to convert carboxylic acids (COOH) to esters
18
Q

Acid chloride convert to ester

A
  • Pyridine or other bases: neutralise the
    HCl generated
  • Alcohols (especially tertiary alcohols) may
    dehydrate under strongly acidic conditions
19
Q

Condensation of acid with amines

A
  • Carboxylic acid + amine
  • Formation of ammonium carboxylate salt (poor electrophile) O- and NH3+R (Not nucleophile)
  • Heat above 100 degrees drives off the water forcing reaction to complete NHR and H2O
20
Q

Acid chloride reaction with ammonium or amides

A
  • Carboxylic acid to acide chloride to amide
  • Addition of NaOH prevents HCL protonating the amine
21
Q

Halide ions

A
  • Good leaving groups for nucleophilc acyl subsitution
  • Acid chloride activated from carboxylic acid
  • Carbonyl O and Cl make acyl strongly electrophilic
22
Q

Thyonyl chloride (SOCl2) or oxylate chloride (COCl2)

A
  • Best reagent to convert Carboxylic acid to Acyl chloride
  • Form gaseous byproduct SO2
23
Q

Carboxylic acid + acid chloride

A

Acid anhydride and HCl

24
Q

Carboxylic acid to primary alcohol

A
  • Carboxylic acid to Acyl chloride to primary alcohol via LiAlH
  • Alderhyde is more reactive compared to carboxylic acids
  • OH is the nucleophile of carboxylic acid
25
Q

Activated forms of the carboxylic acid

A
  • Ester
  • Amide
  • Nitriles
26
Q

Inactivated forms of carboxylic acid

A
  • Acyl halide
  • Anhydride
27
Q

Primary amide

A
  • CONH2 there are no alkyl groups
28
Q

Secondary amide or N substituted amide

A
  • Has one alkyl group attached to the nitrogen
  • CONHR
29
Q

Tertiary amide or N, N substitued amide

A
  • Has two alkyl group attached to the nitrogen
  • CONR2
30
Q

Lactams

A

Cyclic amino acids + H2O

31
Q

Nitriles

A
  • Contain CN group
  • Addition of H2O and H+ or OH- to a nitrile
  • Formation of an amine with H2O and H+ forms carboxylic acid
32
Q

Carboxylic acid to nitriles

A
  • NH3 and heat CONH2
  • Addition of POCl3 is -CN
  • CN bond angle 180 and Sp hybridised
33
Q

Anhydryide +H2O

A
  • Formation of two carboxylic acids
34
Q

Addition of nucleophile to acid anhydride

A
  • Nucleophile attached to carbonyl and acyl chloride
35
Q

Nucleophilic acyl substitution

A
  • One nucleophile replaces another on acyl carbon atom forming tetrahedral intermediate
  • Addition elimination of the leaving group regenerate carbonyl
36
Q

Favourable reaction with acids

A
  • Convert more reactive acid derivative to less reactive depending on structure and attacking nucleophile
  • (Low) Carboxylate, Amide, Ester and Acid chloride (High)
  • Strong base not good leaving group

PMP 102 Drugs & Medicines (56 decks)

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