Organic Chemistry Flashware
Prev. Page

Sorted by Hornback, Organic Chemistry, 2nd Edition

Flashware Title

Textbook Section

Lewis Structure: ethane

1.5, 2.1

Lewis Structure: ethene

1.5, 2.1

Lewis Structure: ethyne

1.5, 2.1

Lewis Structure: bromoethane

1.5, 2.1

Lewis Structure: methanol

1.5, 2.1

Lewis Structure: ethanol

1.5, 2.1

Lewis Structure: ethanal

1.5, 2.1

Lewis Structure: ethanimine

1.5, 2.1

Lewis Structure: ethanitrile

1.5, 2.1

Lewis Structure: nitromethane

1.5, 2.1

Lewis Structure: ethyl carbocation

1.5, 1.7, 2.1

Lewis Structure: ethyl carbanion

1.5, 1.7, 2.1

Lewis Structure: ethenyl carbanion

1.5, 1.7, 2.1

Lewis Structure: propynyl carbanion

1.5, 1.7, 2.1

Lewis Structure: methanol (protonated)

1.5, 1.7, 2.1

Lewis Structure: methoxide anion

1.5, 1.7, 2.1

Lewis Structure: ethanoate anion

1.5, 1.7, 2.1

Lewis Structure: methylamine anion

1.5, 1.7, 2.1

Lewis Structure: methylammonium cation

1.5, 1.7, 2.1

Skeletal Structure: codeine

2.4

Skeletal Structure: cholesterol

2.4

Skeletal Structure: clovene

2.4

Electron Configuration

3.1

Molecular Orbitals: LCAO theory

3.2

Molecular Orbitals: C—C sigma bonds

3.3

Molecular Orbitals: C—H sigma bonds

3.3

Hybridization: sp3

3.3

Localized Molecular Orbital Explorer: ethane

3.3

Hybridization: sp2

3.4

Molecular Orbitals: pi bonds

3.4

Localized Molecular Orbital Explorer: ethene

3.4

Hybridization: sp

3.5

Localized Molecular Orbital Explorer: ethyne

3.5

Resonance: carbonyl group

1.8, 3.6-3.8

Resonance: carbonyl group (protonated)

1.8, 3.6-3.8

Resonance: alkoxyalkyl carbocation

1.8, 3.6-3.8

Resonance: acylium ion

1.8, 3.6-3.8

Resonance: nitrile (protonated)

1.8, 3.6-3.8

Resonance: formate anion

1.8, 3.6-3.8, 4.8

Resonance: carboxylate anion

1.8, 3.6-3.8, 4.8

Resonance: enolate anion

1.8, 3.6-3.8, 4.8

Resonance: amide

1.8, 3.6-3.8

Resonance: allyl carbocation

1.8, 3.6-3.8

Resonance: allyl carbanion

1.8, 3.6-3.8

Resonance: ynolate anion

1.8, 3.6-3.8

Resonance: propynyl carbanion

1.8, 3.6-3.8

Resonance: ethanitrile anion

1.8, 3.6-3.8

Resonance: 1,3-pentadienyl carbocation

1.8, 3.6-3.8

Resonance: 1,3-pentadienyl carbanion

1.8, 3.6-3.8

Resonance: benzene

1.8, 3.6-3.8, 16.2

Resonance: ortho-xylene

1.8, 3.6-3.8, 16.2

Arrow Pushing: Bronsted-Lowry acid H—A

4.1, 4.2

Arrow Pushing: Bronsted-Lowry acid H—A+

4.1, 4.2

Proton Transfer: B + H—A

4.1, 4.2

Proton Transfer: B + H—A

4.1, 4.2

Proton Transfer: B + H—A+

4.1, 4.2

Henderson-Hasselbalch Equation

4.9, 4.10, 26.2

Functional Group Explorer

Chaps. 5, 12

Arrow Pushing: nucleophiles/electrophiles

8.1, 8.6

Arrow Pushing: form/break C—X sigma bond

8.6

Arrow Pushing: form/break C—X+ sigma bond

8.6

Arrow Pushing: nucleophilic substitution (Nu + R—L)

8.3

Arrow Pushing: nucleophilic substitution (Nu + R—L+)

8.3

SN2 Reaction: general mechanism

8.1, 8.2, 8.3, 10.2, 10.6, 10.8

SN2 Reaction: CH3Cl + OH

8.1, 8.2, 8.3, 10.2

SN2 Reaction: 2-chlorobutane + OH

8.1, 8.2, 8.3, 8.4

SN2 Reaction: Williamson ether synthesis

8.1, 8.2, 8.3, 10.3

SN1 Reaction: general mechanism

8.1, 8.2, 8.6, 8.8, 10.2

SN1 Reaction: AcO + R3CCl

8.1, 8.2, 8.6, 8.8

SN1 Reaction: tBuOH + HCl

8.1, 8.2, 8.6, 8.8, 8.9, 10.5

Epoxide Opening (basic conditions)

8.6, 10.1

Epoxide Opening (acidic conditions)

8.3, 10.1

SN2' Reaction

N/A

Carbocation Rearrangement: 1,2-hydride shift

8.14

Carbocation Rearrangement: 1,2-alkyl shift

8.14

E2 Elimination

9.1, 9.2, 9.3, 9.4, 10.11, 10.12

E1 Elimination

8.14, 9.1, 9.5, 9.6

E1cb Elimination

9.1, 9.5, 9.6

Alcohol Dehydration

10.13

Oxidation of Alcohols

10.14

HydroHalogenation of Alkenes

11.1, 11.2

Hydration of Alkenes

11.1, 11.3

Halogenation of Alkenes

11.1, 11.4

Halohydrin Formation

11.1, 11.5

Oxymercuration-Reduction

11.1, 11.6

Hydroboration-Oxidation of Alkenes

11.1, 11.7

Epoxidation (with peracid)

11.9

Electrophilic Aromatic Substitution: general mechanism

17.1-17.4

Electrophilic Aromatic Substitution: halogenation

17.1-17.4, 17.5

Electrophilic Aromatic Substitution: nitration

17.1-17.4, 17.5

Electrophilic Aromatic Substitution: sulfonation

17.1-17.4, 17.6

Electrophilic Aromatic Substitution: Friedel-Crafts alkylation

17.1-17.4, 17.7

Electrophilic Aromatic Substitution: Friedel-Crafts acylation

17.1-17.4, 17.8

Nucleophilic Aromatic Substitution

17.11

Arrow Pushing: carbonyl addition (basic conditions)

18.1

Arrow Pushing: carbonyl addition (acidic conditions)

18.1

Addition to Carbonyl: general mechanism (acidic conditions)

18.1

Addition to Carbonyl: general mechanism (basic conditions)

18.1

NaBH4 Reduction of Aldehydes/Ketones

18.1, 18.2

LiAlH4Reduction of Aldehydes/Ketones

18.1, 18.2, 19.7

Hydration of Aldehydes/Ketones (acidic conditions)

18.1, 18.3

Hydration of Aldehydes/Ketones (basic conditions)

18.1, 18.3

Cyanohydrin Reaction

18.1, 18.4

Grignard Reaction of Aldehydes/Ketones

18.1, 18.6, 19.9

Wittig Reaction

18.1, 18.7

Imine Formation

18.1, 18.8

Hemiacetal and Acetal Formation (acidic conditions)

18.1, 18.9

Cyclic hemiacetal

18.9, 25.3

Conjugate Addition

18.10

Arrow Pushing: collapse of tetrahedral intermediate (basic conditions)

19.1

Arrow Pushing: collapse of tetrahedral intermediate (acidic conditions)

19.1

Substitution at Carbonyl: general mechanism (basic conditions)

19.1

Substitution at Carbonyl: general mechanism (acidic conditions)

19.1

Ester Hydrolysis (basic conditions)

19.5

Ester Hydrolysis (acidic conditions)

19.5

Fischer Esterification

19.4

Amide Hydrolysis (basic conditions)

19.5

Amide Hydrolysis (acidic conditions)

19.5

Transesterification (basic conditions)

19.5

Esterification (via acid chloride)

19.?

Amide Formation (via anhydride)

19.6

Ketone tautomerization (basic conditions)

20.1

Ketone tautomerization (acidic conditions)

20.1

Enolate Alkylation

20.3

Aldol Condensation (basic conditions)

20.5

Claisen Ester Condensation

20.6

Michael Reaction

20.10

Diels-Alder Reaction: general mechanism

22.5, 22.6

Diels-Alder Reaction: cyclopentadiene + ethene

22.5, 22.6

Diels-Alder Reaction: cyclopentadiene + maleic anhydride

22.5, 22.6

[2+2] Photoaddition

22.7

Sigmatropic Rearrangement: [1,3] alkyl shift

22.8

Sigmatropic Rearrangement: [1,3] hydride shift

22.8

Sigmatropic Rearrangement: Claisen rearrangement

22.8

Sigmatropic Rearrangement: Cope rearrangement

22.8

Copyright © 2007, Ghislain Deslongchamps