Drill: Draw

1
Drill Draw Name Reactants Products of

• Oxidations of
• 1-butanol in 2 steps

2
Drill Draw Name Reactants Products of
Oxidation of 2-butanol
3
Drill Draw Name 3 isomers containing carboxyl
groups of
C5H10O2
4
Drill Draw Name 4 isomers containing carboxyl
groups of
C6H12O2
5
Acid Derivatives
6
Acid Anhydrides
7
Acid Anhydrides

• O O
• R1-C-O-C-R2

8
Acid Anhydrides

• Formed through the dehydration of two carboxylic
  acids

9
Making Anhydrides

• O O
• R1-C-OH HO-C-R2

10
General Anhydride

• O O
• R1-C-O-C-R2
• H2O

11
Making Anhydrides

• O
• CH3-C-OH
• O
• HO-C-CH3

12
Diacetic Anhydride

• O O
• CH3-C-O-C-CH3
• H2O

13
Succinic Acid
O C C O
H2C OH H2C OH
Heat
14
Succinic Anhydride
O C C O
H2C O
H2O H2C
15
Phthalic Acid
O C C O
OH OH
Heat
16
Phthalic Anhydride
O C C H2O O
O

17
Anhydride Hydrolysis

• The reverse of the anhydride formation reaction

18
Acyl Group

• O
• R-C-

19
Acyl Group

• O
• CH3-C-
• Acetyl Group

20
Drill

• Draw the reactants, then predict, draw, name
  the product of the dehydration of the combination
  butanoic acid propanoic acid.

21
Esters
22
Esters

• O
• R1-C-O-R2

23
Esterification

• The formation of esters

24
Esterification

• O
• R1-C-OH HO-R2

Acid
25
Ester

• O
• R1-C-O-R2
• H2O

26
Name R P

• O
• CH3-C-OH
• HO-CH3

Acid
27
O
Methanol
OH HO-CH3
OH
HCl
Salicylic Acid
28
Methyl Salicate
O
O-CH3
OH H2O
Oil of Wintergreen
29
Esterification
Acetic Anhydride
O
OH O
C-CH3 C-CH3
OH O
O
Salicylic Acid
30
Acetyl salicylic A
O
Acetic acid
OH O

C-CH3
HO
O
C-CH3
O
Aspirin
31
Drill Draw name 5 esters that are isomers of
C6H12O2
32
Common Esters
33
Ethyl Formate

• O
• H-C-O-CH2-CH3
• Rum

34
Octyl acetate

• O
• H3C-C-O-(CH2)7-CH3
• Oranges

35
Pentyl acetate

• O
• H3C-C-O-(CH2)4-CH3
• Bananas

36
Ethyl butyrate

• O
• H2C-C-O-CH2-CH3
• CH2-CH3
• Pineapples

37
Pentyl butyrate

• O
• H2C-C-O-(CH2)4-CH3
• CH2-CH3
• Apricots

38
Methyl butyrate

• O
• H2C-C-O-CH3
• CH2-CH3
• Apples

39
Predict Product

• O
• CH3-CH2-CH2-C-OH
• O
• HO-C-CH3 Heat

40
Common Biological Ester

• O
• H2C-OH HO-C-R1
• O
• HC-OH HO-C-R2
• O
• H2C-OH HO-C-R3

41
Triglyceride

• O
• H2C-O-C-R1
• O
• HC-O-C-R2
• O 3 H2O
• H2C-O-C-R3

42
Common Biological Ester

• H2C-OH HO-PO3-2
• O
• HC-OH HO-C-R2
• O
• H2C-OH HO-C-R3

43
Phosphoglyceride

• H2C-O-PO3-2
• O
• HC-O-C-R2
• O 3 H2O
• H2C-O-C-R3

44
Drill

• Draw the reactants, then predict draw the
  products of dehydration synthesis when phenol is
  added to formic acid.

45
Ester Hydrolysis

• Adding water to an ester in acid or base to break
  it down into an acid an alcohol

46
Ester Hydrolysis

• O
• R1-C-O-R2

base H2O
47
Acid Alcohol

• O
• R1-C-OH HO-R2

48
Polyester

• A polymer made up of monomers connected by ester
  bonds

49
Making Polyesters

• O O
• HO-C-R-C-OH
• HO-R2-OH

50
Thioesters

• O
• R1-C- S-R2

51
Thioesters

• In thioesters, the single bonded oxygen is
  replaced with sulfur

52
Making Thioesters

• Addition of a thiol to an acid or an anhydride

53
Acid Thiol

• O
• R1-C-OH HS-R2

54
Acid Thiol

• O
• R1-C-OH HS-R2

55
Thioesters

• O
• R1-C- S-R2 H2O

56
Making a Common Thioester

• O
• CH3-C-OH HS-CoA

57
Making a Common Thioester

• O
• CH3-C-OH HS-CoA

58
Acyl Group

• O
• CH3-C-S-CoA
• Acetyl CoA

59
Phosphoric Acid

• O
• HO-P-OH
• OH

60
At pH 7 ish

• O O
• -O-P-OH -O-P-O-
• OH OH

61
P A Anhydrides

• O O
• HO-P-OH HO-P-OH
• OH OH

Heat
62
P A Anhydrides

• O O H2O
• HO-P-O-P-OH
• OH OH

63
Phospho Esters

• O
• HO-P-OH HO-R
• OH

Heat
64
Phosphoesters

• O
• HO-P-O-R
• OH H2O

65
Phosphodiesters

• O
• HO-P-OH HO-R
• OH H-O-R

66
Phosphodiesters

• O
• HO-P-O-R
• O-R 2 H2O

67
Phosphorylation

• Transfer of this phosphoryl group through
  phosphoester bonds

68
Inorganic Ester

• H2C-OH HO-NO2
• HC-OH HO-NO2
• H2C-OH HO-NO2

69
Nitroglycerin

• H2C-O-NO2
• HC-O-NO2 3 H2O
• H2C-O-NO2

70
Draw Name 5 acid or acid derivative containing
isomers of

• C3H6O3

71
Drill

• Draw the reactant, then predict, draw, name the
  products for the hydrolysis of Propylthioacetate.

72
Acid Review
73
Be familiar with the common acids for matching
74
Be familiar with how to oxidize alcohols
75
Be familiar with DH rxns making acid derivatives
76
Be familiar with hydrolysis of acid derivatives
77
Be able to draw name isomers with carboxyls
78
Name

• OH

79
Name

• OH
• OH