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Ochem 2 > Ch 20: Carboxylic acids and they are derivatives: NAS Rxn > Flashcards

Ch 20: Carboxylic acids and they are derivatives: NAS Rxn Flashcards

1
Q

Compounds with parallel properties to carboxylic acids…

A

R-C triple bond N:

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2
Q

The week base who’s conjugate acid has the highest PKA is the ___________. 

A

Strongest

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3
Q

How do you name acyclic acid chlorides by IUPAC?

  • acid chlorides come from carboxylic acids
A

-end in -oyl chloride

Ex:ethanoyl chloride

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4
Q

How do you name acid chloride that are in a ring compound by IUPAC? 

A

Cycloalkane name + carbonyl chloride

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5
Q

How do you commonly name acid chlorides?

A

Prefix + -yl chloride

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6
Q

Acid anhydrates derive from…..

A

Two carboxylic acids

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7
Q

How do you name Symmetrical acid anhydrides?

A

Prefix + -ic anhydride

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8
Q

How do you name mix anhydrides?

A

-two Prefixes + anhydride (alphabetically) 

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9
Q

Esters are made of an _____ and an _____ group.

A

Acyl, alkyl

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10
Q

What is the IUPAC and common naming for esters?

A

IUPAC—— -oate

Common —— -ate

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11
Q

How do you name special ring compounds that include Esther‘s?

A

Name R’ + name of cycloalkane ring + carboxylate

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12
Q

How do you name primary acyclic Amides by IUPAC?

A
  • amide

-  names end in amide or Carboxamide 

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13
Q

How do you name cyclic primary amides by IUPAC?

A

Cycloalkane name + carboxamide

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14
Q

how do you name amides by the common name?

A

Prefix + -amide

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15
Q

How do you name secondary and tertiary amides by the common name? 

A

N- prefix before each R’ group

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16
Q

How do you name nitriles by IUPAC?

A

Name ends in -nitrile

-named as alkanenitriles

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17
Q

How do you name nitriles by their common name?

A

-onitrile

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18
Q

-CN as a substituent is an ________ group 

A

Cyano

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19
Q

Esters and amides have a higher priority than… 

A

Nitriles, alcohols, ketones

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20
Q

Primary and secondary amides have ______ bonds Between their molecules

A

Hydrogen

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21
Q

L what kind of intermolecular forces do acid chlorides, esters, amides, acid anhydrides, and nitriles have?

A

Dipole dipole interactions and van der Waals forces

Primary and secondary amides have hydrogen bonding as well 

  • have higher BP and MP of comparable nonpolar substances of similar molar mass, primary and secondary amides even higher. 
22
Q

Conjugated carbonyl groups absorb at ________ Frequencies

A

Lower

23
Q

As carbonyl ring size decreases, carbonyl groups absorb at _________ frequencies

A

Higher

24
Q

Peptides, polypeptide, proteins are _____ 

A

Amides

25
Q

What is used to synthesize aspirin?

A

Acetic anhydride

26
Q

What is a carboxylate?

A

Conjugate base of carboxylic acid

27
Q

Since Cl is The best leaving group among these compounds, ____________ Are difficult to prepare through acyl nucleophilic substitution reaction

A

Acid chlorides 

28
Q

What is added to remove the HCl formed with an acid chloride reaction?

A

Pyridine (neutralizes) 

29
Q

Reactions with acid chloride and carboxylate ions produce

A

Acid anhydride

30
Q

Reaction with acid chloride and water produces….

A

A carboxylic acid

31
Q

Acid anhydrides are _______ reactive than acid chloride

A

Less

32
Q

Reaction of acid anhydride With water produces….

A

Two carboxylic acids

33
Q

Reaction with acid anhydride with alcohols produce…

A

An Ester and a carboxylic acid

34
Q

Acid-base reactions are _______ Than nucleophilic ones

A

Faster

35
Q

What is required in the conversion of dicarboxylic acids to cyclic anhydrides? 

A

High Heat

36
Q

What reagent is used in Fisher esterfication? 

Carboxylic acid to an ester

A

H2SO4

37
Q

What reagent is used for intramolecular cyclization of Gamma and Delta hydroxy carboxylic acids? 

A

H2SO4

Produces gamma-lactone and H2O

38
Q

What is DCC?

A

A drying agent

39
Q

What reagent is used to convert carboxylic acids to primary amides? 

A
  1. NH3

2. heat

40
Q

Esters undergo what three types of reactions?

A
  • hydrolysis in acid
  • hydrolysis in base
  • Reactions with amines
41
Q

What reagent is used for ester hydrolysis in acid?

What does it produce?

A

H2SO4

 carboxylic acid and alcohol

Because it is reversible, a large excess of water is used to drive the reaction to the right

42
Q

What reagent is used for Ester hydrosis in base?

What does it produce?

A

OH-
H2O

Carboxylate ion and an alcohol

43
Q

Carboxylate ion can be converted to a carboxylic acid with a.….

A

Strong acid

44
Q

-NH2 is a poor leaving group therefore, ________ Are least reactive OK sometimes covered in the unit. However, they do hydrolyze under strenuous conditions in acid or base

A

Amides

45
Q

What reagent is used for hydrolysis of amides in acid?

What is produce?

A

H2O
H+

Carboxylic acid and an ammonium ion

46
Q

What is produced in hydrolysis of amides in base?

What is the reagent?

A

A carboxylate ion and an amine

H2O
OH-

47
Q

The lack of reactivity of ________ amides make Proteins very stable in the body

A

Amides

48
Q

Nitros do not have leaving groups therefore they do not undergo what type of reactions? What reacting do they go?

A

Nucleophilic substitution reaction

Nucleophilic addition reactions at the electrophilic carbon

49
Q

What reagent is needed for the reduction of nitriles?

A

Strong reducing agent

  1. LiAlH4
  2. H2O

Reduces to an amine?

50
Q

Reduction of nitriles with
1.DIBAL-H
2.H20
Produces an….

A

Aldehyde

51
Q

What reagent is used to produce a ketone from nitriles?

A
  1. R’M

2. H2O

Ochem 2 (10 decks)

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