Organic Chemsitry Reagents, Nucleophiles, Bases, Etc.

Chapter 7-8

Iodide Anion

Strong Nucleophile

Chloride Anion

Strong Nucleophile

Bromide Anione

Strong Nucleophile

HS Anion

Strong Nucleophile

RS Anion

Strong Nucleophile

RO Anion

Strong Nucleophile

OH Anion

Strong Nucleophile

CN Anion

Strong Nucleophile

Strong Nucleophile + Strong Base

SN2/E2 (The more substituents, the more E2 is major product)

Ex. Primary: SN2 is the major product

Ex. Secondary: E2 is the major product

Ex. Tertiary: E2 is the only product

Strong Nucleophile + Weak Base

SN2 will be the only product expect when the subtrate is tertiary then it will be SN1

Weak Nucleophile + Strong Base

E2 at all levels of substituents

Weak Nucleophile + Weak Base

SN1 and E1

Tosalyte Group

Converts a poor leaving group (ex. alcohol) into a good leaving group. It is a very weak base and good leaving group.

Triflate Group

Converts a poor leaving group (ex. alcohol) into a good leaving group. It is an extremely weak base and an excellent leaving group.

NaOH (Primary)

Converts alkyl halide to an alcohol or an alkyl tosalyte to an alcohol

HBr (Primary)

Converts alcohol into an alkyl halide

TsCl, py (Primary)

Converts an alcohol to an alkyl tosalyte

t-BuOK (Primary)

Converts an alkyl tosalyte to an alkene or an alkyl halide into an alkene

DBU and DBN (Primary)

Converts alkyl halide into an alkene

NaOCH3 (Primary)

Converts an alkyl halide into an ether

NaSH (Primary)

Converts an alkyl halide into a thiol

CH3CO2Na (Primary)

Converts alkyl halide into an ester

NaCN (Primary)

Converts an alkyl halide into a nitrite

HBr (Teritary)

Converts alcohol into alkyl halide

H2O (Tertiary)

Converts alkyl halide to alcohol

conc. H2SO4 (tertiary)

Converts alcohol to zaistev alkene

TsCl, py (tertiary)

Converts alcohol to alkyl tosalyte

NaOH (tertiary)

Converts alkyl tosalyte or alkyl halide to a zaistev alkene

t-BuOK (tertiary)

Converts alkyl tosalyte or alkyl halide to a Hofmann alkene

Hydrohalogenation

A reaction that involves the addition of H and X (either Br or Cl) across an alkene.