Study Union 2020 Review with NancyCHM 2211 Organic Chemistry II with Dr. Daoudi

Not all of these questions will be covered during the Study Union Review, this is an additional resource for you to study. You do not have to do ALL of the questions, I would suggest to focus on the chapters that have challenged you the most.Disclaimer: These practice problems have been made by your SI Leader based on the textbook and lecture materials, it has NOT been reviewed by your professor. There may be mistakes present, if you believe there is an error in one of the problems please report this to your SI Leader.

Chapter 16:

1) Draw all possible resonance structures showing the lone pairs and curved arrows.

a)

b)

c)

Draw the product(s) of the reactions, label if they are a 1,2 or 1,4 product.

2)

3)

Chapter 16: Draw the starting material for the Diels-Alder product.4)

Draw the Diels-Alder Product.5)

6)

Chapter 17:7) Classify each compound as aromatic, anti-aromatic, or non-aromatic and briefly give your reasoning.

a) d)

b)

e)

c)

X = Cl or Br

8) Name the following benzene structures.

a) b) c)

9) How many 13C NMR signals and 1H NMR signals does each compound have. Are the 1H NMR signals split? what peaks would you expect to see in the IR spectra?

a) b) c)

Chapter 18:

10) Draw the general mechanisms with all potential reagents used in the reactions outlined below. Including intermediates and resonance structures will help with comprehension.

a)

b)

R = alkyl group

c)

d)

e)

f)

g)

h)

i)

j)

11) Circle all the carbons where a substituent would be directed, identify the electron withdrawing and donating groups, and note if they are ortho, meta, or para directors.

a) b) c)

d) e) f) g)

12) What are the defining features or peaks of IR and 1H NMR spectra for aromatic compounds?

Chapter 19:

13) Name the following carboxylic acids.

a) b) c)

14) Rank the compounds below by increasing boiling point.

a) b) c) d)

15) Rank the compounds below by increasing acidity.

a) b) c) d)

16) What peaks would be seen in 13C NMR, 1H NMR, and IR for the following compounds.

a) b) c)

CH3OH

NaBH4

H2 (excess)

Pd-C

(R)-CBS reagent

H2O

1) LiAl[OC(CH3)3]3

2) H2O

17) Write in the reagents used and draw the synthesized carboxylic acid product from the starting material.

a)

b)

c)

Chapter 20:

Draw the product of the following reduction and oxidation reactions.

18)

19)

20)

21)

1) DIBAL-H2) H2O

1) LiAlH4

2) H2O

1) LiAlH4

2) H2O

1) Ag2O

2) NH4OH

CrO3

H2SO4, H2O

22)

23)

24)

25)

26)

1) PhMgBr

2) H2O

1) CH3CuLi

2) H2O

1) CH3CH2CH2Li (2 equiv.)

2) H2O

2) H3O

1) CO2

1) CH3MgBr

2) H2O

27)

28)

29)

30)

31)

1) CH3CuLi

2) H2O

1) PhMgBr

2) H2O

Determine if the reaction will be a 1,2 or 1,4 addition and draw the product.

32)

33)

Chapter 21:

34) Name the following aldehydes and ketones.

a) b) c) d) e)

35) Write the reagents used and draw the synthesized aldehyde and/or ketone product from the starting material.

a)

b)

c)

Ph3PCH2

CH3(CH2)2NH2

mild acid

d)

e)

f)

Draw the product of the following nucleophilic addition reactions.

37)

38)

39)

mild acid

C4H8NH

H2O

+ 2 C5H9OHTsOH

TsOH+

40)

41) Draw the mechanism for the hydration product of the compound under acidic and basic conditions.

Draw the intermediate hemiacetal (if synthesized) and the acetal product for the following reactions.

42)

43)

[1] TsOH

[2] CH3OH, H+

1) SOCl2

2) C5H11N (2 equiv.)

44)

Chapter 22:

45) Rank the following carboxylic acid derivatives by increasing reactivity.

a) b) c) d)

46) Name the following carboxylic acid derivatives.

a) b) c) d) e) f)

Draw the product(s) of the reactions (note: some reactions are multistep).

47)

HOCH2CH(CH3)2

H2SO4

48)

49)

50)

51)

52)

H3O+/OH-

1) NaCN

2) LiAlH4 (2 equiv.)3) H2O

1) DIBAL-H

2) H2O

1) NaCN

2) PhMgBr3) H2O

53) Show the products formed with the acid and with the base

54)

55)

56)

Cl2

CH3COOH

Chapter 23:57) Draw the tautomer(s) for the following compounds.

a)

b)

c)

d)

58) Fill in the reagents and products for kinetic and thermodynamic enolate formation of the compound below, include the product tautomers.

Draw the product(s) of the reactions.

59)

1) KOC(CH3)3

EtOH, 25℃

2)

1) LDA, THF, -78

2)

Br2 (excess)-OH

Br2 (excess)

-OH

60)

61)

62)

63)

1)

2)

3) , !

1) (2 equiv.)

2)

3) , !

64)

65)

Chapter 24:Draw the product for the aldol-based ractions.

66)

67)

68)

69)

70)

71)

Draw the product for the Claisen-based reactions.

72)

73)

74)

75)

Draw the product of the Michael addition and Robinson annulation reactions.

76)

77)

78)

79)

Chapter 25:

80) Name the the following amine compounds.

a) b) c) d)

e) f)

81) What are the defining peaks you would see in IR, MS, and 1H NMR for amines? Do any of these peaks change between primary, secondary, and tertiary amines?

excess

2 equivalents

1)

2)

3)

1)

2)

NaBH3CN

Draw the product of the amine synthesis reactions.

82)

83)

84)

85)

86)

(2 equiv.)

mild acid

mild acid

Rank the amines in order of increasing basicity.

87)a) b) c) d)

88)

a) b) c) d)

89)

90)

91)

(excess)1)

2)3)

Cl-

+

Cl-

+

92)

93)

94)

95)

96)

Cl-+

97)

Chapter 27:

Assign R and S configuration to each of the chiral carbons and convert the Fischer projections to the Haworth projections and chair conformations written below.

98) β-Haworth α-chair

99) β-Haworth α-Haworth

100) β-Haworth furanose β-Haworth pyranose

Draw the chair conformations of the reagents and products in the following monosaccharide reactions.

102) α-D-glucose 1) CH3CH2CH2OH, HCl2)H3O+

103) β-D-galactose AcClpyridine

104)

105)

106) Draw the products when glucose reacts with NaBH4 with CH3OH, Ag2O with NH4OH, and HNO3 with H2O.

Draw the chair conformations of the following disaccharides

107) A galactose and glucose joined by a beta 1-4 glycosidic bond.

108) Two glucose joined by an alpha 1-4 glycosidic bond.

Chapter 29:

Draw the product(s) of the following coupling reactions.

109)

110)

111)

112)

113)

114)

115)

Chapter 31:Draw the monomer for the following polymers (include brackets to indicate the monomer unit).

116) Poly(hexamethylene adipamide) aka nylon

117) Polyethylene

118) Poly(tetrafluoroethene) aka teflon

119) Poly(phenylethane) aka polyvinyl benzene aka polystyrene

120) Match the hypothetical structures to the type of polymer.

a) Alternating Copolymer

b) Block Copolymer

c) Graft Copolymer

d) Homopolymer

e) Random Copolymer

Draw the product of the polymerizing reactions below, use the number of monomers indicated in the reaction.

121)

122)

123)

124)

125)

126)

127)

128)

129)

130) Draw simple sequence of monomers that represent isotactic, syndiotactic, and atactic polymers.

131) Briefly define TM and TG.

You made it!The very best of luck on your Orgo exam

and all of your exams this week.

The best advice I have ever received before an examwas to remember all the information is in your head,

just trust that it is there, and crush that test!

Had to crop it to make it SFW, but you get the point :))