Organic Reactions and Conditions

Reduction of an alkyne to a Z-alkene:

Lindlar’s catalyst, H₂

Reduction of an alkyne to an E-alkene:

Na, NH_3(l)

Oxymercuration or hydroboration of an alkene affords an …

alcohol

Oxymercuration affords the … substituted alcohol

more

Hydroboration affords the … substituted alcohol

less

Oxymercuration of an alkene:

1. Hg(OAc)₂, H₂O in THF

2. NaBH₄

Hydroboration of an alkene:

1. H-BR₂

2. H₂O₂, NaOH

cis-dihydroxylation of an alkene:

1. OsO₄, NMO, H₂O

2. acetone or tert-butanol

Epoxidation of an alkene:

mCPBA

Opening of an epoxide:

1. H₂O and H⁺

OR

1. H₂O and OH^-

trans-dihydroxylation of an alkene:

1. mCPBA

2. H₂O with either OH^- or H⁺

Diels-Alder reaction mechanism:

1. diene

2. dienophile

heat

Oxymercuration or hydroboration of an alkyne affords an …

enol

The enol formed from oxymercuration or hydroboration of an alkyne … to form either an … or a …

tautomerises, aldehyde, ketone

Wittig reaction:

phosphorus ylid reacts with carbonyl compound, affords an alkene

room temperature or gently heat

Elimination of an alkene to form an alkyne:

strong base (e.g. LDA)

Ozonolysis of an alkene to form an aldehyde or ketone:

1. O₃, CH₂Cl₂

2. Zn, HCl or Ph₃P or Me₂S

-78°C

Ozonolysis of an alkene to form a carboxylic acid:

1. O₃, CH₂Cl₂

2. H₂O₂

-78°C