Organic Chemistry Reagents

conc. H₂SO₄, heat

E1

Alcohol --> Alkene

regioselective - more substituted double bond

stereoselective - trans(E)>cis(Z)

Rearrangement around tertiary alcohol

HCl

Sn1

Alcohol --> Alkyl halide

regioselective - tertiary alcohol

HBr (3)

Sn1/Sn2:

Alcohol --> Alkyl halide

Sn1- secondary and tertiary, Sn2 - primary

Free Radical:

Alkene --> alkyl bromide

markovnikov

HBr Addition:

Alkyne --> alkene

markovnikov, anti-addition

SOCl₂, base

Sn2

Alcohol --> Alkyl chloride

primary and secondary alcohols

PBr₃

Sn2

Alcohol --> alkyl bromide

primary and secondary alcohol

Na₂Cr₂O₇ or CrO₃, H₂SO₄ **

oxidation

alcohol --> carbonyl

produces carboxylic acid in the presence of water when primary

H₂CrO₄

oxidation

alcohol --> carbonyl

produces carboxylic acid in the presence of water when primary

PCC or PDC, CH₂Cl₂

oxidation

alcohol --> carbonyl

HIO₄

oxidation

alcohol (2) --> carbonyl (2)

*alcohol must be in syn

Br₂ w/ heat, light

free radical

alkane --> alkyl bromide

regioselective for tertiary hydrogen

Cl₂ w/ heat, light

free radical

alkane --> alkyl chloride

regioselective for equivalent hydrogens

O₂

combustion

alkane --> carbon dioxide + water

2NaNH₂, NH₃

E2

vicinal or geminal dibrominde --> Alkyne

3NaNH₂, NH₃ followed by acid workup

E2

vicuna or geminal dibromide -- alkyne

*only when it's a terminal alkyne

1. BH₃, THF

2. H₂O₂, NaOH

Hydrobroration

alkene --> alcohol

anti-markovnikov, syn-addition

H: hydride shift, OH: water

dilute H₂SO₄

Acid-Catalyzed

alkene --> alcohol

markovnikov

OsO₄, catalyst

Hydroxylation

Alkene --> Alcohol (2)

syn-addition

Br₂ or Cl₂, H₂O, CH₂Cl₂, cold/dark

Electrophilic addition

alkene --> alcohol/alkyl halide

Alcohol: Markovnikov

Halide: anti-Markovnikov

anti-addition

Br₂ or Cl₂, CH₂Cl₂, cold/dark

Electrophilic addition

alkene --> alkyl halide (2)

anti-addition

H₂, metal catalyst (2)

Hydrogenation...

Alkene --> alkane

syn-addition

Hydrogenation...

carbonyl --> alcohol

Peroxyacetic Acid (RC(=O)OOH)

Epoxidation

Alkene --> Epoxide

Same side of DB = same side of ring

1. O₃

2. H₂O, Zn or S(CH₃)₂

Oxidative Cleavage

Alkene --> Ketone or Aldehyde

1. O₃

2. H₂O

Ozonolysis

Alkene --> Ketone or Carboxylic Acid

Oxonolysis

Alkyne --> Carboxylic Acids

H₂O

Hydrolysis

Alkyl halide --> alcohol

Strong Base, Heat

E2

Alkyl halide --> alkene

more substituted double bond

trans (E)>cis(Z)

Beta hydrogen and halide MUST be anti

Williamson Ether Synthesis

Sn2

alkoxide ion + alkyl halide --> Ether

regioselective: primary alkyl halides

NaOH

Sn2

vicinal halohydrin--> epoxide

Backside attack

Halide and oxygen must be anti

inversion of configuration

H₂SO₄, HOCH₂CH₃

ring-opening

Epoxide --> alcohol

markovnikov

1. NaOCH₂CH₃, HOCH₂CH₃

2. Aqueous Acid

ring-opening

Epoxide --> alcohol

anit-markovnikov

1. Organometallic (Grignard)

2. Acid Workup

Grignard

Carbonyl --> Alcohol

anion attacks C; hydrogen on oxygen results from acid workup

1. LiAlH₄

2. Acid Workup

LiAH

Carbonyl --> alcohol

hydrogen attacks C; hydrogen on oxygen results from acid workup

NaI, acetone

Sn2

bromide --> iodide

inversion of configuration

NaNH₂, NH₃

Alkyne --> Alkyne (-)

Excess of H₂, Pd

Hydrogenation

Alkyne --> alkane

H₂, Lindlar Pd

Semi-Hydrogenation

Alkyne --> Alkene

Cis

Na, NH₃

Semi-Hydrogenation

alkyne --> alkene

trans

2HBr or 2HCl

HBr Addition

Alkyne --> Geminal Dihalide

markovnikov

Br₂ or Cl₂

X₂ Addition

alkyne --> alkene

anti-addition

2Br₂ or 2Cl₂

X₂ Addition

alkyne --> tetrahaloalkane

anti-addition

H₂SO₄, H₂O, HgSO₄

Acid Catalyzed Hydration

Alkyne --> Enol/Tautomer

markovnikov

tautomerization occurs to more DB to create a carboxyl group

HBr Peroxides

Free Radical:

Alkene --> alkyl bromide

anti-markovnikov

HBr Addition:

alkyne --> alkene

anti-markovnikov

1. BH₃-THF

2. NaOH, H₂O₂

alkene --> alcohol

anti-markovnikov

syn-addition

H₂SO₄, heat

ether synthesis

2 alcohols --> ether

only works with symmetrical, primary alcohols