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Organic Chemistry II > Chapter 21: Carboxylic Acids and Their Derivatives > Flashcards

Chapter 21: Carboxylic Acids and Their Derivatives Flashcards

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1
Q

H3O+, Heat with cyanide group

A

Hydrolysis of Nitriles

-forms carboxylic acid

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2
Q

BH3 THF with carboxylic acid

A

Reduction of Carboxylic Acids with Borane

-selectively reduces carboxylic acids to alcohols

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3
Q

1)LAH, 2)H3O+ with carbonyl

A

Reduction of Carboxylic Acids with LAH

  • the alcohol group is first deprotenated
  • this is because the LAH is not a good nuc but instead a good base
  • the carbonyl attacks the Al, while the hydride from LAH attacks the carbonyl carbon
  • the anion oxiygen then pushes its electron density down and expels the O-AlH2
  • another hydride atttacks to form an alkoxide
  • H3O+ is added at this point, to protenate the alkoxide
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4
Q

SOCl2 with carboxylic acid

A

Preparation of Acid Chlorides

  • carbonyl forms excellent LG with SOCl
  • Cl- that was expelled attacks carbonyl and displaces SO2Cl, forms SO2, Cl-
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5
Q

H2O with Acid Chloride

A

Hydrolysis of Acid Chlorides

  • H2O nuc attacks carbonyl
  • Cl leaves as LG
  • H2O is deprotenated
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6
Q

ROH, Pyridine with Acid Chloride

A

Alcoholysis of Acid Chlorides

  • ROH nuc attacks carbonyl
  • Cl leaves as LG
  • ROH is deprotenated
    • pyrdine is used to neutralize HCl
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7
Q

2 NH3 with Acid Chloride

A

Aminolysis of Acid Chlorides

  • NH3 nuc attacks carbonyl
  • Cl leaves as LG
  • NH3 is deprotenated
    • pyrdine is used to neutralize HCl
    • canwork for primary and secondary amines
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8
Q

1)Excess LAH 2) H2O with Acid Chloride

A

Reduction of Acid Chlorides

  • LAH delivers hydride
  • carbonyl reforms, expells Cl
  • LAH delivers hydride
  • H2O protenated alkoxide ioN
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9
Q

1)LiAl(OR)3H 2)H2O with Acid Chloride

A

Reduction of Acid Chloride

-reaction with aldehyde occurs more slowly, so reaction simply produces carbonyl

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10
Q

1) Excess RMgBr 2)H2O with Acid Chloride

A

Acid Chloride and Grignard Reagent

  • R- nuc attacks carbonyl
  • carbonyl reforms, expels Cl
  • R- attacks again
  • H2O protenates alkoxide ion
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11
Q

R2CuLi with Acid Chloride

A

Reaction between Acid Chlorides and Organometallic Reagents
0Cu forms less polarized bonds
-can produce ketones

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12
Q

800 deg C with carboxylic acid

A

Preparing Acid Anhydride
Can convertcarboxylic acid to acetic anhydride
-only useful for acetic acid
-forms H2O as side product

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13
Q

Carboxylate ion with acid chloride

A

Preparing Acid Anhydride

-nuc attack and loss of Cl

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14
Q

1) NaOH 2) R-I with carboxylic acid

A

Preparation of Esters via SN2

  • carboxylate ion acts as nuc that attacks the R gorup
  • tert alkyl halides don’t work
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15
Q

R-OH, [H+] with carboxylic acid

A

Preparation of Esters Via Fisher Esterification

  • carbonyl on carboxylic acid is protenated
  • acid attacks carbonyl C
  • acid deprotenated
  • hydroxyl protenated
  • carbonyl reforms, pushes off H2O
  • carbonyl deprotenated
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16
Q

ROH, Pyridine with Acid Chloride

A

Preparation of Esters Via Acid Chlorides

  • ROH nuc attacks carbonyl
  • Cl leaves as LG
  • ROH is deprotenated
    • pyrdine is used to neutralize HCl
17
Q

1) NaOH 2) H3O+ with ester

A

Saponification

  • BASIC conditions
  • OH attacks carbonyl
  • OR leaves
  • OR is protenated by OH
  • carboxylate ion must thenbe protenated in 2nd step
18
Q

H3O+ with ester

A

Acid-Catalyzed Hydrolysis of Esters

  • carbonyl is protenated
  • H2O attacks carbonyl
  • H2O deprotenated
  • O-R protenated
  • carbonyl reforms, ester-H leaves
  • carbonyl deprotenated
19
Q

NH3

A

Aminolysis of Esters

Slow reaction, not as practical as acid chloride

20
Q

1)Excess LAH 2) H2O with ester

A

Reduction of Esters

  • LAH delivers hydride
  • carbonyl reforms, expells R-O
  • LAH delivers hydride
  • H2O protenated alkoxide ion
21
Q

DIBAH, low temp. with ester

A

Reduction of Esters

-stops reduction at aldehyde

22
Q

1) Excess RMgBR 2)H2O with ester

A

Grignard Reaction with Esters

  • Two R groups and an OH as product
  • R- nuc attacks carbonyl
  • carbonyl reforms, expels RO
  • R- attacks again
  • H2O protenates alkoxide ion
23
Q

H3O+ heat with amide

A

Acid Catalyzed Hydrolysis of Amides

  • carbonyl is protenated
  • H2O attacks carbonyl
  • H2O deprotenated
  • NH2 protenated
  • carbonyl reforms, NH3 leaves
  • carbonyl deprotenated
24
Q

1)NaOH, heat 2) H3O+ with amide

A

Base-Catalyzed Hydrolysis of Amides

  • BASIC conditions
  • OH attacks carbonyl
  • OR leaves
  • NH2 is protenated by OH
  • carboxylate ion must thenbe protenated in 2nd step
  • deprotenation of carboxylic acid makes reaction irreversible
25
Q

NaCN with alkyl halide

A

Preparation and Reactions of Nitriles
Via SN2 Reactions
Cyanide replaces halide

26
Q

SOCl2 with nitrile

A

Preparation and Reactions of Nitriles
Via Amides
-carbonyl double bond attacks S, N lone pair forms double bond
-S-O forms carbonyl expels Cl
-Base deprotenated NH2
-Base deprotenates NH, forms triple bond (N-C) and O-S forms double bond, Cl expelled

27
Q

H3O+, Heat with nitrile

Acid-catalyzed

A 
Hydrolysis of Nitriles
N is protenated with H3O+
-H2O attacks C
-H2O is deprotenated 
-NH is protenated
[resonance: OH forms carbonyl, NH gets e- from double bond]
-carbonyl is deprotenated
-forms amide
28
Q

1)NaOH, H2O 2)H3O+ wth nitrile

A 
Base-catalyzed 
Hydrolysis of Nitriles
--OH attacks C
-N is protenated
-Oh deprotenated
[resonance: O- forms carbonyl]
-N- is  protenated
29
Q

1) RMgBr 2)H3O+ with Nitrile

A

Reactions With Grignard Reagents and Nitriles

  • grignard attacks carbonyl, forms N-
  • treated with acid to form imine
  • hydrolyzed to ketone under acidic conditions
30
Q

1) Excess LAH 2) H2O

A

Reductions of Nitriles

-Forms amine at end of carbon

Organic Chemistry II (10 decks)

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