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1
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5
Q

Walk through the logic for determining which substitution or elimination reaction if….

R-group is tertiary

A

1. R-group is tertiary: No SN2

2. Is Nuc/Base a strong base?

Yes: alkene product via E2

No: Proceed to next question

3. Is the solvent polar protic?

Yes: substitution and or elimination via fast SN1 and E1; SN1 slightly preferred over E1

No: slow substitution and/or elimination via SN1, E2, and E1, or no reaction

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6
Q

(alkene reaction)

Provide the reagents for:

12) Hydrogenation

A
  1. REDUCTION WTF reaction
  2. No rearrangement
  3. Syn
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6
Q

Walk through the logic for determining which substitution or elimination reaction if….

R group is secondary

A

1. Is the Nuc/Base a strong base?

Yes: alkene product via E2

No, proceed to next question:

2. Is the Nuc/Base a good to moderate nucleophile?

Yes: substitution product via moderate speed SN2

No: proceed to next question:

3. Is the solvent polar protic?

Yes: substitution and or elimination via moderate speed SN1 and E1

No: substitution via slow SN2

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7
Q

(alkene reaction)

What is the function of:

H2O2

[Ozonolysis (Oxidative)]

A

Presumably used for oxidation

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7
Q

What is the function for:

CH3-OH
[Alkoxymercuation]

(alkene reaction)

A

Generic alcohol that substitutes for H2O in similar oxymercuration mechanism.

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8
Q

(alkene reaction)

What is the function of:

H2O2

[Radical Hydrohalogenation]

A

Creates a radical pathway for Anti-Markovnikov addition of H-X to a double bond

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9
Q

(alkene reaction)

What is the function of:

Hg(OAc)2
[Oxymercuration]

A

Functions like an X2 by creating an ion ring intermediate and allowing the Markovnikov addition of H2O to the double bond. Advantage is that it can be removed by NaBH4

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9
Q

What is the function of:

OsO4
[Dihydroxylation/Diol formation]

(alkene reaction)

A

By some orgo magic, can grab both sides of a double bond and eventually disappear for syn diol addition.

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9
Q

Alkene naming: Z

A

Z= zame (same)

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9
Q

Alkene naming: E

A

E= oppositE

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9
Q

Alkenes of 5 or more carbon atoms have what physical state?

A

Colorless liquids that are less dense than water

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10
Q

Are alkenes polar or non-polar?

A

Alkenes are non-polar

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10
Q

Alkenes of two, three and four carbon atoms have what physical state?

A

Gases at room temperature

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10
Q

C13 NMR readout predicts what?

C13 NMR: 0-50 ppm

A

C13 NMR: What region contains signals from sp3 hybridized carbon atoms?

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11
Q

C13 NMR readout predicts what?

C13 NMR: 50-100 ppm

A

C13 NMR: What region contains signals from

(1) sp3-hybridized carbons that are deshielded by electronegative atoms, AND
(2) sp-hybridized carbon atoms

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11
Q

C13 NMR readout predicts what?

C13 NMR: 100-150 ppm

A

C13 NMR: What region contains signals from sp2 hybridized carbon atoms?

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11
Q

C13 NMR readout predicts what?

C13 NMR: 150-220 ppm (usually 200 ppm)

A

C13 NMR: What region contains signals from carbon atoms of carbonyl groups. Highly deshiedled.

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12
Q

C13 NMR: What region contains signals from

(1) sp3-hybridized carbons that are deshielded by electronegative atoms, AND
(2) sp-hybridized carbon atoms

A

C13 NMR: 50-100 ppm

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13
Q

C13 NMR: What region contains signals from carbon atoms of carbonyl groups. Highly deshiedled.

A

C13 NMR: 150-220 ppm (usually 200 ppm)

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14
Q

C13 NMR: What region contains signals from sp2 hybridized carbon atoms?

A

C13 NMR: 100-150 ppm

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15
Q

C13 NMR: What region contains signals from sp3 hybridized carbon atoms?

A

C13 NMR: 0-50 ppm

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18
Q

Draw a terpene unit

A

llama!!

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19
Q

Draw propylene

A
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19
Q

Draw phenyl

A
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19
Q

draw methylene

A
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20
Q

Draw Tosylate (OTs- )

A
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21
Q

Draw vinyl

A
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23
Q

Identify

A

Acetaldehyde

(Acet-aldehyde)

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25
Q

Identify

A

Decalin

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26
Q

Identify

A

Norbornane

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27
Q

Identify

A

Acetone

(acet-one)

this is a ketone

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27
Q

Identify

A

Acetic acid

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28
Q

Identify

A

Acetone

(acet-one)

this is a ketone

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28
Q

Identify

A

Acetaldehyde

(Acet-aldehyde)

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28
Q

Identify the common name

A

Benzene

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29
Q

Identify

A

Acetic acid

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29
Q

Identify the common name

A

Isobutylene

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29
Q

Identify the common name

A

Vitamin A

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30
Q

Identify the common name

A

Propylene

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31
Q

Identify the common name of the alkenyl group

A

Methylene

The example is therefore named: methylenecyclopentane

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32
Q

Identify the common name

A

Norbornene

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33
Q

Identify the common name

A

Nicotinamide (niacin)

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33
Q

Identify the common name

A

Ethylene

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34
Q

Identify the common name of the alkenyl group

A

Vinyl

The example is therefore named: Vinylcyclopentane

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35
Q

Identify the common name of the alkenyl group

A

Allyl

The example is therefore named: Allylcyclopentane

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36
Q

Identify the common name:

A
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38
Q

Identify the common name:

A
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40
Q

Identify the common name:

A
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41
Q

Identify the common name:

A
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42
Q

Identify the common name:

A
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44
Q

Identify the common name:

A
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44
Q

Identify this common NMR pattern

A

Ethyl group

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44
Q

Identify the functional group in the IR spectra

A

Alcohol

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44
Q

Identify the functional groups in the IR spectra

A

Carboxylic Acid

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44
Q

Identify the functional groups in the IR spectra

45
Q

Identify this common NMR pattern

A

tert-butyl

47
Q

Identify this common NMR pattern

48
Q

IR spectra: ester

49
Q

IR spectra: Alkane

50
Q

IR spectra: Alkane measurement

51
Q

IR spectra: Alkene

52
Q

IR spectra: Alkene measurement

53
Q

IR spectra: Alkyne

54
Q

IR spectra: Alkyne measurement

55
Q

IR spectra: Ketone measurement

56
Q

Isomerism with alkenes

A
  • For an alkene with one carbon-carbon double bond that can show cis, trans isomerism: two steroisomers possible
  • For an alkene with n carbon-carbon double bonds, each of which can show cis, trans isomerism: 2^n stereoisomers possible
57
Q

J value: cis

58
Q

J value: geminal

59
Q

J value: trans

61
Q

Let’s say your molecular formula has oxygen and you notice the below chemical shift, what does it imply?

  • +2.5 ppm
A
  • Oxygen of alcohol or ether
63
Q

Let’s say your molecular formula has oxygen and you notice the below chemical shift, what does it imply?

  • +3 ppm
A
  • Oxygen of an ester
65
Q

Let’s say your molecular formula has oxygen and you notice the below chemical shift, what does it imply?

  • +1 ppm
A
  • Carbonyl group
67
Q

(alkene reaction)

Name all anti-addition reactions

A
  1. Halogenation
  2. Halohydrin formation
  3. Oxymercuration
  4. Alkoxymercuration
69
Q

(alkene reaction)

Name all syn-addition reactions

A
  1. Hydroboration
  2. Syn-Diol Formation (OsO4 Oxidation)
  3. Syn-Diol Formation (KMnO4 Oxidation)
  4. Pt/Pd reduction
71
Q

(alkene reaction)

Provide the reagents for:

1) Acid catalyzed hydration

A
  1. Markovnikov
  2. Possible rearrangement
  3. Syn/anti do not apply
73
Q

(alkene reaction)

Provide the reagents for:

10) Ozonolysis (Reduction step 2)

A
  • Oxidation/reduction WTF reaction
  • No rearrangement
  • Syn/anti do not apply
75
Q

(alkene reaction)

Provide the reagents for:

11) Ozonolysis (Oxidation step 2)

A
  • Oxidation/reduction WTF reaction
  • No rearragement
  • Syn/anti do not apply
76
Q

(alkene reaction)

Provide the reagents for:

2) Hydrohalogenation

A
  1. Markovnikov
  2. Possible rearrangement
  3. Syn/anti do not apply
77
Q

(alkene reaction)

Provide the reagents for:

3) Halogenation

A
  1. Markovnikov rules apply
  2. Bridge formation: No rearragement
  3. Anti
78
Q

(alkene reaction)

Provide the reagents for:

5) Oxymercuration

A
  1. Markovnikov rules apply
  2. Bridge formation: No rearrangement
  3. Anti
80
Q

(alkene reaction)

Provide the reagents for:

6) Alkoxymercuration

A
  1. Markovnikov rules apply
  2. Bridge formation: No rearrangement
  3. Anti
82
Q

(alkene reaction)

Provide the reagents for:

7) Hydroboration

A
  1. ANTI-Markovnikov
  2. No rearrangement
  3. Syn
84
Q

(alkene reaction)

Provide the reagents for:

8) Syn-diol formation (OsO4 oxidation method)

A
  1. Oxidation/reduction WTF reaction
  2. No rearragement
  3. Syn
85
Q

(alkene reaction)

Provide the reagents for:

9) Syn-diol formation (KMnO4 method)

A
  1. Oxidation/reduction WTF reaction
  2. No rearrangement
  3. Syn
86
Q

(alkene reaction)

Provide the reagents for:

13) Radical, Anti-Mark HX Addition

A
  1. ANTI-Markovnikov
  2. No rearragement
  3. Syn/anti does not apply
87
Q

(alkene reaction)

Provide the reagents for:

4a) Halohydrin formation (alcohol)

A
  1. Markovnikov rules apply
  2. Bridge formation: No rearrangement
  3. Anti
88
Q

(alkene reaction)

Provide the reagents for:

4b) Halohydrin formation (ether)

A
  1. Markovnikov rules apply
  2. Bridge formation: No rearrangement
  3. Anti
89
Q

Summary of E1 Versus E2 Reactions for Haloalkanes

90
Q

Summary of E1 Versus E2 Reactions for Haloalkanes

91
Q

Summary of E1 Versus E2 Reactions for Haloalkanes

92
Q

Summary of SN1 versus SN2 of haloalkanes

93
Q

Summary of SN1 versus SN2 of haloalkanes

94
Q

Summary of SN1 versus SN2 of haloalkanes

95
Q

Summary of SN1 versus SN2 of haloalkanes

96
Q

Summary of SN1 versus SN2 of haloalkanes

97
Q

Summary of substitution vs. elimination reactions for haloalkanes

A

SN1/E1: not observed

SN2: only reaction

E2: not possible

SN1 reactions of methyl halides are never observed because the methyl cation is so unstable it is not observed in common solvents.

98
Q

Summary of substitution vs. elimination reactions for haloalkanes

A

SN1/E1: primary reaction if: weak nucleophiles in polar protic solvents, such as water, methanol, and ethanol.

SN2: Primary reaction if: bases/nucleophiles where pka of the conjugate acid is 11 or less, as for example I- and CH3COO-

E2: Primary reaction if: bases/nucleophiles where pka of the conjugate acid is 11 or greater, as for example OH- and CH3CH2O-

99
Q

Summary of substitution vs. elimination reactions for haloalkanes

A

SN1/E1: Primary reaction if: poor nucleophiles/weak bases if the solvent is polar protic

SN2: Never observed b/c of extreme crowding around the tertiary carbon

E2: Main reaction with strong bases such as HO- and RO-

100
Q

Summary of substitution vs. elimination reactions for haloalkanes

A

SN1/E1: not observed

SN2: primary reaction if: Good nucleophiles and weak base (I- or CH3COO-)

E2: primary reaction if: Strong, bulky bases [(CH3)3CO-]

Neither SN1 nor E1 likely due to primary cations rarely being formed in solution

101
Q

Walk through the logic for determining which substitution or elimination reaction if….

R-group is primary and sterically unhindered

A

1. R-group is primary: no SN1/ E1

2. Is the Nuc/Base a strong base and hindered?:

If yes, alkene product via E2 (rare)

If no, proceed to second question:

3. Is the Nuc/Base a good nucleophile?:

If yes, substitution product via rapid SN2 (common)

If no, substitution product via slow SN2

103
Q

What are the only attractive forces between alkene molecules?

A

Dispersion forces

105
Q

What does an HDI of zero indicate?

A
  • compound does not possess any rings or pi bonds
106
Q

What does an HDI of 4 indicate?

A
  • Indicates the likely presence of an aromatic (benzene) ring
107
Q

What is a phenyl group: draw it and list all abbreviations

A

A more specific reference for a certain type of aryl group:

In organic chemistry, the phenyl group or phenyl ring is a cyclic group of atoms with the formula C6H5. Phenyl groups are closely related to benzene. Phenyl groups have six carbon atoms bonded together in a hexagonal planar ring, five of which are bonded to individual hydrogen atoms, with the remaining carbon bonded to a substituent

In essence, it is a benzene ring with ONLY ONE substituent

Abbreviations:

  1. C6H5–
  2. Ph–
108
Q

What is an aryl group: draw it and list all abbreviations

A

In the context of organic molecules, aryl refers to any functional group or substituent derived from an aromatic (benzene) ring.

In essence, it is any benzene ring with one or more substituents. VERY GENERAL.

Abbreviations:

  1. Ar–
109
Q

What is the chemical shift?

A

4.5- 6.5 ppm

111
Q

What is the chemical shift?

113
Q

What is the chemical shift?

114
Q

What is the chemical shift?

116
Q

What is the chemical shift?

118
Q

What is the chemical shift?

A

6.5 -8 (normally 7) ppm

119
Q

What is the chemical shift?

120
Q

What is the chemical shift?

121
Q

What is the chemical shift?

122
Q

What is the chemical shift?

123
Q

What is the chemical shift?

124
Q

What is the function for:

DMS (Dimethyl Sulfide) / Zn
[Ozonolysis (reductive)]

(alkene reaction)

A

Presumably used for reduction

125
Q

(alkene reaction)

What is the function of:

BH3 / THF
[Hydroboration]

A

EN difference between H and B actually favors H, giving H a negative charge and B a positive charge, which leads to the syn addition of BH3 to double bonds and the formation of a square intermediate

126
Q

(alkene reaction)

What is the function of:

CH2Cl2 / CCl4
[General Addition, Halogenation]

A

Generic organic solvent. Doesn’t really do anything, but it’s designed to not get in the way

127
Q

(alkene reaction)

What is the function of:

H2O
[Halohydrin Formation, Acid-Catalyzed Hydration]

A

Used as a nucleophile in the first and as a base to deprotonate in the second

128
Q

(alkene reaction)

What is the function of:

H2O2
[Hydroboration]

A

Used with NaOH to remove BH2+ intermediate

129
Q

(alkene reaction)

What is the function of:

Hg(CF3COO-)2
[Alkoxymercuration]

A

Functions the same as Hg(OAc)2

Functions like an X2 by creating an ion ring intermediate and allowing the Markovnikov addition of the alcohol to the double bond. Advantage is that it can be removed by NaBH4

130
Q

(alkene reaction)

What is the function of:

HX, X = halogen
[General Addition]

A

Acidic H from polarized H-X bond easily adds to a double bond

131
Q

(alkene reaction)

What is the function of:

KMnO4
[Dihydroxylation/Diol formation, Ozonolysis (Oxidative)]

A
  • K is just used to form a salt. Behaves like OsO4 under cold and dilute conditions (By some orgo magic, can grab both sides of a double bond and eventually disappear for syn diol addition.)
  • Under heat or acidic conditions, will follow the ozonolysis (oxidative) pathway
132
Q

(alkene reaction)

What is the function of:

NaBH4
[Oxymercuration]

[Alkoxymercuration]

A

Used to remove Hg based intermediate

133
Q

(alkene reaction)

What is the function of:

NaOH
[Hydroboration]

A
  • Used with H2O2 as a strong base to remove the BH2+ intermediate
  • Often used to supply OH-, which is used in deprotonation steps
134
Q

(alkene reaction)

What is the function of:

X2, X= halogen
[Halogenation, Halohydrin Formation]

A

Most halogens are found as diatomic gases. Covalence allows X-X bond to break rather easily when polarized by a double bond

135
Q

(alkene reaction)

What is the function of:

H2SO4
[Acid-Catalyzed Hydration]

A

Used as a strong acid generate hydronium ion (H3O+), which is a starting reactant for the hydration. A good strong acid to use since the conjugate base does not compete with the double bond of the alkene as a nucleophile.

136
Q

What is the pka of:

CH2=CH2

A

CH2=CH2 pka=44

137
Q

What is the pka of:

CH3CH3

A

CH3CH3 pka=50

140
Q

What is the pka of:

NH3

A

NH3 pka=36

141
Q

What is the pka of:

HC[triple bond]CH

A

HC[triple bond]CH pka=25

142
Q

What is the shift effect, and draw the NMR puzzle piece for:

  • The alpha position of an alkyl group near the oxygen of an alcohol or ether
A

Effect: +2.5 ppm

143
Q

What is the shift effect, and draw the NMR puzzle piece for:

  • The alpha position of an alkyl group near the oxygen of an ester
A

Effect: +3 ppm

144
Q

What is the shift effect, and draw the NMR puzzle piece for:

  • The alpha position of an alkyl group near the a carbonyl group
A

Effect: +1 ppm

145
Q

What is the term used to classify benzene and its derivatives?

A

Arene or aromatic

146
Q

Based on a chemical shift in the range below, predict the type of proton

~0.9 ppm

A

What is the chemical shift?

147
Q

What is the pka of:

H2O

A

H2O pka = 15.7

147
Q

What is the pka of:

HF

A

HF pka=3.2

148
Q

Based on a chemical shift in the range below, predict the type of proton

~1.2 ppm

A

What is the chemical shift?

149
Q

Based on a chemical shift in the range below, predict the type of proton

~1.7 ppm

A

What is the chemical shift?

150
Q

Based on a chemical shift in the range below, predict the type of proton

~10 ppm

A

What is the chemical shift?

151
Q

Based on a chemical shift in the range below, predict the type of proton

~12 ppm

A

What is the chemical shift?

152
Q

Based on a chemical shift in the range below, predict the type of proton

~2 ppm

A

What is the chemical shift?

153
Q

Based on a chemical shift in the range below, predict the type of proton

~2-4 ppm

A

What is the chemical shift?

154
Q

Based on a chemical shift in the range below, predict the type of proton

~2.5 ppm

A

What is the chemical shift?

155
Q

What does an HDI of 1 indicate?

A
  • Compound has either a ring or one pi bond

Organic Chemistry (6 decks)

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