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Organic Chemistry > Chapter 20: Carboxylic Acids and Their Derivatives > Flashcards

Chapter 20: Carboxylic Acids and Their Derivatives Flashcards

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1
Q

Naming carboxylic acids

A
  1. Identify and name the parent chain that includes the carboxyl group
  2. Identify and name substituents
  3. Assign locant to each substituent giving the carboxyl carbon the lowest number
  4. Assemble substituents alphabetically
  5. Assign configurations to any chiral centers
  6. Replace “e” with suffix −oic acid
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2
Q
A

Cyclohexanecarboxylic acid

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3
Q
A

Formic acid

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4
Q
A

Acetic acid

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5
Q
A

Propionic acid

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6
Q
A

Butyric acid

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7
Q
A

Benzoic acid

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8
Q

Naming deprotonated carboxylic acids

A

Replace the “ic acid” with the suffix −ate

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9
Q

Average pKa for carboxylic acids

A

4−5

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10
Q

Henderson-Hasselbach equation

A
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11
Q

Preparing a carboxylic acid from an alkyne

A

Reagents

  1. O3
  2. H2O
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12
Q

Preparing a carboxylic acid from a primary alcohol

A

Reagents

Na2Cr2O7 (sodium dichromate) & H2SO4/H2O

or

xs CrO3 (chromium trioxide) & H3O+/acetone

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13
Q

Preparing a carboxylic acid from an alkylbenzene

A

Reagents

Na2Cr2O7 (sodium dichromate) & H2SO4/H2O

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14
Q

Preparing a carboxylic acid from a nitrile

A

Reagents

H3O+ & heat

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15
Q

Preparing a carboxylic acid from a Grignard reagent

A

Reagents

  1. Mg

Followed by

  1. CO2
  2. H3O+

Mechanism

Replaces the leaving MgX group withe the carboxyl group; resulting in the addition of one carbon atom

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16
Q

Reduction of carboxylic acids

A

Reagents

  1. LiAlH4
  2. H3O+

or

BH3 (borane) & THF

Mechanism

Borane is chemoselective and only reduces carboxyl groups in the presence of other carbonyl groups

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17
Q

What is a heteroatom

A

Any atom that is not carbon or hydrogen

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18
Q

Naming acid halides

A

Replace “ic acid” with suffix −yl halide

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19
Q

Naming acid anhydrides

A

Replace “acid” with suffix −anhydride

If molecule is asymmetrical then the compound is called −oic −oic anhydride

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20
Q

Naming esters

A
  1. Add name of the oxygen R −yl group before the parent chain −ate
  2. Replace “ic acid” with suffix −ate
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21
Q

Naming amides

A
  1. Replace “ic acid” with suffix −amide
  2. If the nitrogen has substituents, then name them with locant “N”
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22
Q

Naming nitriles

A

Replace “ic acid” with suffix −nitrile

23
Q

Reactivity of carboxylic acid derivatives

A

Carboxylic acid derivatives are electrophilic at the carbonyl carbon

Acid chlorides are the most reactive derivatives

Amides are the least reactive derivatives

24
Q

Nucleophilic acyl substitution

Basic reaction mechanism

A

Can occur under acidic or basic conditions

Mechanism

A nucleophile attacks a carbonyl carbon and forms a tetrahedral intermediate, the carbonyl can then be reformed by the expulsion of the best leaving group

C− and H− are generally not expelled as leaving groups

25
Q

Preparing an acid chloride from a carboxylic acid

A

Reagents

SOCl2 (thionyl chloride)

26
Q

Preparing a carboxylic acid from a acid chloride

A

Reagents

H2O & Pyridine

Mechanism

Water functions as a nucleophile and the chloride is ejected as a LG

Pyridine is used as a base to react with the HCl byproduct and prevent it from performing unwanted side reactions

27
Q

Alcoholysis of acid chlorides

A

Reagents

ROH & Pyridine

Mechanism

Alcohol oxygen and R group are acylated to produce an ester

Reaction can also be viewed from the perspective of the acid chloride

28
Q

Aminolysis of acid chlorides

A

Reagents

NH3, RNH2, or R2NH (two equivalents)

Mechanism

An amide is formed through the acylation of the amine group with the loss of one hydrogen atom from the amine reagent

Pyridine is not required because the amine is sufficiently basic enough to neutralize the HCl as it forms; hence why two equivalents are required

29
Q

Reduction of acid chlorides

Forming a primary alcohol

A

Reagents

  1. LiAlH4
  2. H2O

Mechanism

Carbonyl carbon is reduced to form a primary alcohol

30
Q

Reduction of acid chlorides

Forming an aldehyde

A

Reagents

  1. LiAl(OR)3H (lithium hydride)
  2. H2O

Mechanism

A bulky lithium hydride reagent will slow down reduction at an aldehyde

31
Q

Preparing a tertiary alcohol from an acid chloride

A

Reagents

  1. Excess RMgBr
  2. H2O

Mechanism

Gringnard reagent R groups are added to the carbonyl carbon with the ejection of the chloride ion

32
Q

Preparing a ketone from an acid chloride

A

Reagents

R2CuLi (dialkyl lithium cuparate)

Mechanism

One of the two alkyl groups adds to make a ketone

33
Q

Nucleophilic acyl substitution reactions of acid anhydrides

A

Anhydrides undergo many of the same reactions as acid chlorides

The leaving group is a carboxylate ion rather than a chloride ion

34
Q
A

Acetic anhydride

35
Q

Acetylation of an alcohol or an amine

A

Reagents

Acetic anhydride

36
Q

Preparing an ester from a carboxylic acid

A

Reagents

  1. NaOH
  2. RX

Mechanism

The carboxylic acid is first deprotonated to yield a carboxylate ion which then functions as a nucleophile and attacks the alkyl halide in an SN2 process

A tertiary alcohol cannot be used due to SN2 mechanism

37
Q

Fischer esterfication

A

Reagents

[H+] & ROH

Mechanism

A carboxylic acid is converted into an ester when treated with an alcohol

Can be reversed with an excess of water under acidic conditions such as in an acid catalyzed ester hydrolysis

Can also be reversed via soaponification

38
Q

Preparing an ester from an acid chloride

A

Reagents

ROH & Pyridine

Mechanism

Alcohol performs a nucleophilic attack on an acid chloride

Reaction can also be viewed from the perspective of the alcohol via alcoholysis reaction

39
Q

Ester hydrolysis

Basic conditions

A

Reagents

  1. NaOH
  2. H3O+

Mechanism

Esters undergo hydrolysis in basic conditions through the hydration of the ester bond in a reaction called saponification

40
Q

Ester hydrolysis

Acidic conditions

A

Reagents

H3O+

Mechanism

The mechanism is a reverse Fischer esterification

41
Q

Aminolysis of esters

A

Reagents

NH3

Mechanism

Ammonia attacks carbonyl carbon to form an amide

Very slow process, easier to make amides from acid chlorides

42
Q

Reduction of esters

Forming an alcohol

A

Reagents

  1. LAH (LiAlH4)
  2. H2O

Esters are NOT sensitive towards NaBH4 reduction

43
Q

Reduction of esters

Forming an aldehyde

A

Reagents

  1. DIBAH
  2. H2O
44
Q

Preparing a tertiary alcohol from an ester

A

Reagents

Mechanism

Esters can react with excess Grignard reagent to form a tertiary alcohol via the addition of two R groups

45
Q

Preparation of amide trends

A

Amides are most efficiently prepared from acid chlorides

46
Q

Hydrolysis of amides

Acidic conditions

A

Reagents

H3O+ & heat

47
Q

Hydrolysis of amides

Basic conditions

A

Reagents

  1. NaOH & heat
  2. H3O+
48
Q

Reduction of amides

A

Reagents

  1. Excess LAH (LiAlH4)
  2. H2O

Mechanism

Produces a primary amine

Water is used to prevent the formation of an ammonium ion

49
Q

Preparing a nitrile from an alkyl halide

A

Reagents

NaCN

Mechanism

Transformation proceeds via an SN2 mechanism so a tertiary alkyl halide CANNOT be used

50
Q

Preparing a nitrile from a primary amide

A

Reagents

SOCl2 (thionyl chloride)

Mechanism

Can be used to prepare tertiary nitriles which cannot be preparred via an SN2 mechanism

51
Q

Hydrolysis of a nitrile

Basic conditions

A

Reagents

  1. NaOH, H2O
  2. H3O+
52
Q

Hydrolysis of a nitrile

Acidic conditions

A

Reagents

H3O+ & heat

53
Q

Preparing a ketone from a nitrile

A

Reagents

  1. RMgBr
  2. H3O+

Mechanism

The Grignard reagent first forms an imine which can then he hydrolyzed to form the ketone

54
Q

Reduction of a nitrile

A

Reagents

  1. Excess LAH (LiAlH4)
  2. H2O

Mechanism

Produces a primary amine

Water is used to prevent the formation of an ammonium ion

Organic Chemistry (18 decks)

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