(guess the name) Reaction Notebook - Baldwin OSU Chem 2510

Radical Halogenation of Alkanes

(X2, hv)

alkane → racemic alkyl halide

SN1

(weak nuc)

2° or 3° alkyl halide → racemic alcohol

SN2

(strong nuc, polar aprotic solv)

1° or 2° alkyl halide → umbrella-flipped substituted alkane

E1

(weak nuc/base, Δ)

2° or 3° alkyl halide → alkene

E2

(strong base, polar aprotic solv)

any alkyl halide → alkene

Ester Hydrolysis

(1. strong nuc

2. strong base)

1° or 2° alkyl halide → alcohol

Reductions [R] of Carbonyls

(1. [R] agent

2. SA)

carbonyl → alcohol

Jones/Chromic Acid Oxidation [O]

(CrO3, H2SO4, H2O)

methanol, 1° or 2° alcohol → carbonyl

Aldehyde Synthesis w/ PCC/PDC [O]

(DCM)

1° or 2° alcohol → aldehyde

Organometallic ABC

(1. THF

2. H2O, HCl)

organometallic → protonated non-metallic hydrocarbon

Organometallic E2

(toluene)

2° alkyl halide → alkene

Organometallic Additions to Carbonyls

(1. THF

2. H2O, HCl)

carbonyl → trisubstituted alcohol

Alkoxide Synthesis

(strong base)

alcohol → alkoxide (a strong nuc!)

Alkyloxonium Synthesis

(SA, H2O)

alcohol → alkyloxonium (a good LG)

Alkyl Halide Syntheses

(multiple options)

alcohol → alkyl halide

Williamson Ether Synthesis

(DMSO)

alkoxide + 1° alkyl halide → ether

Intramolecular Ether Synthesis

([R] agent, THF)

halohydrin → epoxide/episulfide

Acidic Ether Synthesis

(SA, H2O)

2 alcohols → ether

Ether Cleavage

(SA, H2O)

ether → alcohol + byprodt

Organometallic Additions w/ Protecting Groups

N/A

Epoxides in Basic Conditions

(1. weak

2. SA, H2O)

epoxide + organometallic → complex alcohol(s)

Epoxides in Acidic Conditions

(HX/salt/[R] agent)

epoxide → complex alcohol

Additions to Alkenes

(X-Y)

alkene → disubstituted alkane

Hydrogenation of Alkenes

(Pd/C, PtO2, or Rainey Nickel, polar protic solv)

alkene → "syn" alkane

HX Additions to Alkenes

(polar protic solv)

alkene → Mark racemic alkyl halide

Racemic Hydration of Alkenes

(H2O)

alkene → Mark racemic alcohol

X2 Additions to Alkenes

(polar aprotic solv)

alkene → vicinal "anti" dihalides

Halohydrin Formation and Other Halonium Uses

(H2O)

substituted alkene → "anti" halohydrin

Oxymercuration-Demercuration Hydration of Alkenes

(1. H2O, Hg(OAc)2

2. [R] agent, NaOH, H2O)

alkene → Mark "anti" alcohol

Hydroboration-Oxidation Hydration of Alkenes

(1. BH3, THF

2. NaOH, H2O2)

alkene → anti-Mark "syn" alcohol

Alkene Ozonolysis

(1. O3, H2O

2. DMS or Zn, CH3COOH)

alkene → carbonyl prodts

Radical Bromination of Alkenes

(HBr, hv, H2O2)

alkene → anti-Mark alkyl bromide

-merization of Alkenes

(H2SO4)

multiple terminal alkenes → complex alkene

Double Elimination Alkyne Synthesis

(1. NH2-, NH3

2. H2O, HCl)

dihalide alkane → alkyne

Synthesis with Alkynyl Anions

(1. strong base, polar aprotic solv

2. many options)

terminal alkyne → internal alkyne

Pd Hydrogenation of Alkynes

(H2, Pd/C, polar protic solv)

alkyne → alkane

Lindlar's Hydrogenation of Alkynes

(H2, Lindlar's, polar protic solv)

alkyne → "syn" alkene

Dissolving Metal Hydrogenation of Alkynes

(1. Na, NH3

2. H2O, HCl)

alkyne → "anti" alkene

HX Additions to Alkynes

(polar protic solv)

alkyne → Mark geminal dihalide

X2 Additions to Alkynes

(polar aprotic solv)

alkyne → quadrihalide

Acidic Tautomerization Hydration of Alkynes

(1. LA

2. H2O, SA)

alkyne → Mark keto form

Basic Tautomerization Hydration of Alkynes

(1. bulky boron reagent

2. NaOH, H2O2)

alkyne → anti-Mark keto form

Radical Bromination of Alkynes

(HBr, hv or Δ, H2O2)

alkyne → anti-Mark vinyl bromide

Alkyne Ozonolysis

(O3, H2O)

alkyne → carboxylic acid prodts

Kinetic Additions to Dienes

(polar aprotic solv)

diene → 1,2-prodt

Thermodynamic Additions to Dienes

(polar aprotic solv)

diene → 1,4-prodt

Alkene Diels-Alder Cycloaddition

(Δ)

diene + dienophilic alkene → cycloalkene

Alkyne Diels-Alder Cycloaddition

(Δ)

diene + dienophilic alkyne → cyclodiene