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Organic Chemistry 2 > Exam 4 > Flashcards

Exam 4 Flashcards

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1
Q

Formic Acid

A
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2
Q

Acetic Acid

A
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3
Q

Propionic Acid

A
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4
Q

Butyric Acid

A
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5
Q

Valeric Acid

A
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6
Q

Benzoic Acid

A
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7
Q

Acrylic Acid

A
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8
Q

Oxalic Acid

A
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9
Q

Malonic Acid

A
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10
Q

Succinic Acid

A
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11
Q

Maleic Acid

A
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12
Q

Phthalic Acid

A
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13
Q

Carboxylic Acid

Common Nomenclature

A

Name substituents with alpha, beta, gamma, delta, etc.

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14
Q

Carboxylic Acid

IUPAC Nomenclature

A

Highest Priority:

suffix = -oic acid

branch = -carboxylic acid

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15
Q

Carboxylate Salt

Nomenclature

A
  1. List complexed salt first
  2. Replate -ic acid with -oate
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16
Q

Acidity of Carboxylic Acids

A

EWG’s on α-C increase acidity of molecule,

but drops off quickly with distance

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17
Q

Acid-Base Extraction

A

Add sodium hydroxide to create the carboxylate salt that stays in the aqueous layer, while the other organic molecules are removed in the ether layer, and recreate the carboxylic acid solid by adding hydorchloric acid.

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18
Q

Mass Spectrometry

McLafferty Rearrangment

A

Peak around 60 m/c that’d indicitive of a carboxylic acid

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19
Q

Primary Alcohol

to

Carboxylic Acid

A

Reagants:

Warm, conc. Na2Cr2O7 / H2SO4

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20
Q

Aldehyde

to

Carboxylic Acid

A

Reagants:

Br2 / H2O or Ag(NH3)2OH

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21
Q

Alkene

to

Carboxylic Acid

A

Reagents:

Warm, conc. KMnO4

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22
Q

Alkyne

to

Carboxylic Acid

A

Reagents:

1) O3, 2) H2O

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23
Q

Alkyl Bromide

to

Carboxylic Acid

A

Reagents:

1) Mg°, 2) CO2, 3) HCl

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24
Q

Carbons with a +3 Oxidation

to

Carboxylic Acid

A

Reagents:

H3O+ / Δ

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25
Q

Methyl Benzene

to

Carboxylic Acid

A

Reagents:

Warm, conc. Na2Cr2O7 / H2SO4

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26
Q

Fischer Esterification

A

Reagents:

Carboxlyic acid + primary alcohol

0.1 eq. p-TsOH

**Not highly favored, 60:40, but more favored when the carboxylic acid and alcohol are on the same molecule **

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27
Q

Indirect Esterification

A

Reagents:

Carboxylic acid

1) SOCl2, 2) Primary Alcohol

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28
Q

Diazomethane Esterification

A

Reagents:

Carboxylic Acid

1) CH2N2 (diazomethane)

**Advantages: high yield, clean reaction: Disadvantages: limited to methyl esters, limited to small scale**

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29
Q

Direct Amidation

A

Reagents:

Carboxylic Acid

1) Primary amine / Δ / H2O (steam)

**Acid/base reaction competes**

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30
Q

Indirect Amidation

A

Reagents:

1) Carboxylic acid + SOCl2
2) Secondary amine

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31
Q

Reducation of Carboxylic Acids

A

Reagents:

1) LAH (strong reducing agent)
2) HCl(aq)

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32
Q

Partial Reduction of Carboxylic Acids

A

Reagents:

Carboxylic Acid → Aldehyde

1) CH2N2, 2) DIBAL-H, 3)H3O+

or

1) SOCl2, 2)LiAl(t-Butyl oxide)3H

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33
Q

Selective Reduction of Carboxylic Acids

A

Reagents:

Oxo Carboxylic Acid → Hydroxy Ketone

1) BH3•THF, 2) HCl

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34
Q

Alkylation of Carboxylic Acids

A

Reagents:

Carboxylic acid → Ketone

1) 2 eq. CH3Li, 2) H3O+

or

1) SOCl2, 2) (CH3)2CuLi

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35
Q

Ester

to

Carboxylic Acid

A

Reagents:

1) NaOH / H2O / HOEt, 2) HCl

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36
Q

What is a derivative of a carboxylic acid?

A

Functional groups that have a carbon in a +3 oxidation state

(A carbon with three bonds to a non-carbon atom, ex: O, N, X)

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37
Q

Reactivity of Carboxylic Acid Derivatives

A
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38
Q

Acid Chloride

Nomeclature

A

Replace -ic acid with -yl chloride

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39
Q

Anhydride

Nomeclature

A

Replace -acid with -anhydride

Unsymmetrical andyrhides: name each carboxylic acid equivalent in alphabetical order, then add -anhydride to the end

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40
Q

Anhydride

to

Carboxylic Acid w/Ester

A

Reagents:

ROH

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41
Q

Esters

Nomenclature

A

Add alkyl group as branch name to beginning of the name, then replace -ic acid with -ate

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42
Q

Cyclic Ester (Lactones)

Nomenclature

A

IUPAC: Add lactone to the end of the carboxylic acid name

Common: Remove hydroxy, then replace -ic acid with -o lactone

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43
Q

Amide

Nomenclature

A

Replace -oic acid / -ic acid with -amide and indicate branches off of the N with N/N’-

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44
Q

Cyclic Amide (Lactams)

Nomenclature

A

IUPAC: Add lactam to the end of the carboxylic acid name

Common: Remove amino and replace -ic acid with -olactam

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45
Q

What are significant structural features of amines?

A

1) Roational barrier between O=C-N bond: caused by the significant double bond character from -O-C=N+ resonance structure.
2) The oxygen is more acidic than the nitrogen, so the oxygen will be protonated first.
3) The hydrogen on the nitrogen is most acidic, so the nitrogen will be deprotonated first.

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46
Q

Nitrile

Nomenclature

A

IUPAC: Add nitrile to base alkane name

Common: Replace -ic acid with -o nitrile

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47
Q

Primary Amide

to

Nitrile

A

Reagents:

P(O)Cl3 or P2O5

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48
Q

Nomenclature for Groups Off a Ring

A
49
Q

Nucleophilic Acyl Substitution

with

Strong Electrophile + Weak Nucleophile

A

Strong E+: acid chlorides, anhydrides

Weak Nu-H: H2O, ROH, RNH2

50
Q

Nucleophilic Acyl Substitution

with

Weak Electrophile + Strong Nucleophile

A

Weak E+: Ester, amide

Strong Nu-: -OH, -OR, -NR2

51
Q

Nucleophilic Acyl Substitution

with

Weak Electrophile activated by H+ + Weak Nucleophile

A

Weak E+: Acid chlorides, anhydrides

H+: p-TsOH

Weak Nu-H: H2O, ROH, HNR2

52
Q

What is suprising about the bp trends of the carboxylic acid derivates?

A

1) Nitriles and primary alcohols have similar bp (nitriles slightly higher than alcohols) even though nitriles cannot hydrogen bond.
2) Tertiary amides being higher than alcohols, nitrils, and acids even though they cannot hydrogen bond. Shows significance of its resonance structure with a significant dipole moment over the O=C-N bonds

53
Q

Why are thioester more reactive than esters?

A

They have poor pi bond overlap because of the longer C-S bond length

54
Q

Carboxylic Acid

Reduced to

Primary Alcohol

A

Reagents:

1) LAH, 2) H3O+ or 1) BH3, 2) H3O+

55
Q

Ester

Reduced to

Primary Alcohol

A

Reagents:

1) LAH, 2) H3O+

56
Q

Ester

Reduced to

Aldehyde

A

Reagents:

1) DIBAL-H, 2) H3O+

57
Q

Acid Chloride

Reduced to

Aldehyde

A

Reagents:

LiAl(t-Butyl oxide)3H

(mild hydride donor)

58
Q

Amide

Reduced to

Amine

A

Reagents:

1) LAH, 2) H2O

59
Q

Nitrile

Reduced to

Primary Amine

A

Reagents:

1) LAH, 2) H2O or H2/Pd

60
Q

Nitrile

Reduced to

Ketone

A

Reagents:

1) CH3MgBr, 2) H3O+

61
Q

Ester

Reduced to

Tertiary Alcohol

A

Reagents:

1) 2 eq. RMgBr, 2) H3O+

62
Q

What is a carbonic acid derivative?

A

Any carbon center with a +4 oxidation center

63
Q

Carbonic Acid

A
64
Q

Carbonate

Nomenclature

A

List the R groups in alphabetical order, followed by carbonate

65
Q

Carbamate / Urethane

Nomeclature

A

List the alkyl group attached to the oxygen, then name the nitrogen branches with the prefix N-

IUPAC: End name with carbamate

Common: End name with urethane

66
Q

Urea

Nomeclature

A

Name the alkyl groups off the nitrogens with the prefixes N, N’- giving the most substituted nitrogen N

End the name with urea

67
Q

Carbonic Acid Derivatives

Starting Materials

A
68
Q

Method of Carbomate and Carbamate Synthesis

via Phosgene / Triphosgene

A
69
Q

Isocyanate Synthesis

A
70
Q

Carbamate Synthesis

Via Isocyanate

A
71
Q

Urea Synthesis

Via Isocyanate

A
72
Q

α - Substitution

A

C center with +2 oxidation state tautomerizes to enol, which acts as a nucleophile to add an electrophile to the α-carbon

73
Q

Acid-Catalyzed Enol Formation

A
74
Q

Base-Catalyzed Enol Formation

A
75
Q

Enol Derivative

Reactivities

A
76
Q

Acidity of Alcohol

A

16

77
Q

Acidity of Ketones

A

19

78
Q

Acidity of Esters

A

24

**Oxygen acts as an EDG, so it makes the α-hydrogen less acidic**

79
Q

Acidity of Amines

A

38

**LDA is an amine, which is why it’s such a good base**

80
Q

Acidity of Ethyl Acetoacetate

A

11

**More acidic than esters because of the second carbonyl = 3 resonance structures**

81
Q

Acidity of Diethyl Malonate

A

13

**Less acidic than ethyl acetoacetate because of both oxygens, but more acidic than esters because of 3 resonance structures**

82
Q

Acidic Halogenation of Carbonyls

(α-Substitution)

A

Acidic conditions favor monohalogenation because first Br makes the enol less nucleophillic (more acidic) than the unsubstituted enol

**Excess reagents will polyhalogenate**

83
Q

Basic Halogenation of Carbonyls

(α-Substitution)

A

Basic conditions favor polyhalogenation because the monosubstituted enol is more acidic than the unsubstituted enol

84
Q

Haloform Reaction

A

**Iodoform commonly used as a methyl ketone test**

85
Q

Brominating Carboxylic Acid

A

Reagents:

1) PBr3 / Br2, 2) H2O / Δ

**PBr3 turns the -OH into a -Br**

86
Q

Direct Alkylation of Enolate Ions

A

Reagents:

Ketone

1) LDA, 2) R-X

**E2 and aldol condensation compete with this reaction**

87
Q

Stork Enamine Alkylation

A

Reagents:

Aldehyde or Ketone

1) HNR2, 2) R’-X, 3) H3O+

88
Q

Alkylation of β-dicarbonyl compounds

A

Reagents:

Acetoacetic ester or Malonate ester

1) NaOEt, 2) R-X, 3) H3O+ / Δ

**Loss of CO2 indicated by [1,3] dicarbonyls after initiation acid hydrolysis**

89
Q

Acid Hydrolysis

A

Reagents:

H3O+ / Δ

90
Q

Aldol Condensation Reaction

A

Reagents:

2 Aldehydes or 1 Aldehyde + 1 Ketone

NaOH / H2O / HOR

**Product typically dehydrates under basic and acidic conditions**

91
Q

Claisen Ester Reaction

A

Reagents:

2 Esters

1) NaOEt, 2) H3O+

**Remember to neutralize basic conditions with Step 2 in mechanism!**

92
Q

Dehydration of Aldol in Basic Conditions

A
93
Q

Dehydration of Aldol in Acidic Conditions

A
94
Q

Well Designed Aldol Condensation

A

Nucleophile with one α-C group

Electrophile with no α-C group

95
Q

Cyclic Aldol Condensation Reaction

A

**Wants to form most stable ring (6 carbons)!!**

96
Q

Dieckmann Ester Condensation

(Cyclic Claisen Reactions)

A
97
Q

What is a Michael Addition Reaction?

A

Adding a nucleophile to a carbonyl in the [1,4] position

**Thermodynamic product, so heat required**

98
Q

What reagents favor [1,2] addition?

A

Strong Nucleophiles:

Grignard (RMgBr)

Organolithium (RLi)

Acetylide Ion (R-C≡C- +Na)

99
Q

What reagents favor a Michael [1,4] addition?

A

Michael Donor: mild to moderate nucleophile

Michael Acceptor: Double bond with an EWG in conjugation

100
Q

Robinson Annulation

(Michael Reaction + Cyclic Aldol Reaction)

A
101
Q

D-(+)-glucose

A
102
Q

D-galactose

A
103
Q

D-fructose

A
104
Q

D-(-)-ribose

A
105
Q

What are epimers?

A

A type of diasteromer that has only a one chiral center difference between the two structures

Ex: D-(+)-allose is the C2 epimer of D-(+)-altrose

106
Q

What are anomers?

A

α anomer = CH2OH and OH groups are trans to each other

β anomer = CH2OH and OH groups are cis to each other

107
Q

How do you convert a Fischer projection to a Haworth projection?

A
108
Q

Hemiacetal

to

Acetal

A

Reagents:

cat. pTsOH / ROH

109
Q

What is a glycoside?

A

It’s a sugar with an aglycone unit attached at the end of the chain

Ex: OR, NR2,OROH, etc. replacing hemiacetal -OH group

110
Q

Enediol Rearrangment

A

Creates two possible sugars:

1) Switch the chirality of the first row
2) Replace the first row with a carbonyl group

111
Q

Complete Oxidation of Sugars

A

Reagents:

HNO3

**Strong oxidizer**

112
Q

Partial Oxidation of Sugars

A

Reagents:

Br2 / H2O or Ag(NH3)2OH

**Mild oxidizer**

113
Q

Reducing Sugars

A

A sugar that contains an aldehyde that can react with Ag+/Cu+ to create Ag/Cu metal

114
Q

Replace acetal -OH groups with -OR groups

A

Reagents:

Excess RI / Ag2O

115
Q

Replace acetal -OH groups with -OAc groups

A

Reagents:

Ac2O / pyridine

116
Q

Reducing Sugars

A

Reagents:

NaBH4

**Mild hydride donor**

117
Q

Phenyl Osazone

A

Reagents:

3 eq. PhNHNH2 / HA / A-

118
Q

Ruff Degradation

A

Reagents:

1) Br2 / H2O, 2) Fe2(SO4)3 / H2O2

119
Q

Fischer-Killiani Chain Lengthening

A

Reagents:

1) NaCN / H2O, 2) H2 / Pd / BaSO4, 3) H3O+

**Produces epimers / 2 products**

Organic Chemistry 2 (4 decks)

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