Organic Chemistry Bridging Review

What are the conditions for an SN1 reaction?

• Occurs in a polar protic solvent, typically in a tertiary substrate

• Involves the formation of a carbocation intermediate

• Favored by weak nucleophiles

• Occurs at room temperature or under mild heating.

Define this mechanism:

Leaving group leaves forming a carbocation which is then attacked by a nucleophile fast

SN!

What are the conditions for an SN2 reaction?

• Requires a polar aprotic solvent and a primary or secondary substrate

• Involves a concerted mechanism where the nucleophile attacks the electrophile simultaneously as the leaving group departs

• Favored by strong nucleophiles

• Often requires animation or heating to support the reaction.

In general, negatively charged nucleophiles are?

SN2

Name the reaction and what is the end product?

Hydroboration

End Product: Alcohol (anti-markovnikoff)

Name the reaction and what is the end product?

Oxymercuration

End Product: Alcohol (markovnikoff)

Name the reaction and what is the end product?

Acid-Catalyzed addition of H2O

End Product: Alcohol (markovnikoff)

Name the reaction and what is the end product?

Addition of Halide

Br

Name the reaction and what is the end product?

Bromination

Anti-addition of bromine

Name the reaction and what is the end product?

Dihydroxylation

Syn-addition of alcohols

Name the reaction and what is the end product?

Epoxidation

Syn-addition of epoxide which can then give diol

Name the reaction and what is the end product?

Hydrogenation

Syn-addition of Hydrogen

Name the reaction and what is the end product?

Radical Addition of Br

Anti-markovnikoff of Br

Name the reaction and what is the end product?

Cyclopropnation

End Product: Carbenoid

Name the reaction and what is the end product?

Ozonolysis

End Product: Ketone or Carboxylic Acid

Name the reaction and what is the end product?

Grignard Reaction:

Tertiary Alcohol

(T/F) The more electron-poor the aldehyde or ketone the more reactive

True

Name the reaction and what is the end product?

Acid Catalysis

More electrophilic carbon

What reagent change an alcohol (OH) to a carbonyl directly?

PCC

What reagent change an alcohol (OH) to a carbonyl using peroxide (HOOH) with it?

R₂BH

What reagent changes an alkene to a ketone?

1) Hg(OAc)₂ 2) H2O and H₂SO₄

What reagent cleaves the C - C pi bond in an alkene forming an 2 aldehyde?

1.) O3 2.) Zn

What reagent will form an imine from a aldehyde?

R-NH2

What reagent forms a Alkene from a aldehyde?

Ph₃P=CH₂ (Witting Reaction)

What reagent oxidizes aldehyde to a carboxylic acid?

H2CrO4 or KMnO4

What reagent reduces an ester to a tertiary alcohol

R-MgCl or R-Li