Master Study Set Map of Chemical Reaction Mechanisms (WE WISH CHEMISTRY B/W INDIVIDUALS WERE THIS SIMPLE)

Strong base, weak nucleophile, FIRST DEGREE

E2

Strong base, weak nucleophile, SECOND DEGREE

E2

Strong base, weak nucleophile, THIRD DEGREE

E2

Order of determining reactions

1. REAGENT

2. SUBSTRATE

3. REGIOCHEMICAL & STEREOCHEMICAL REQUIREMENTS

Strong base, strong nucleophile, THIRD DEGREE

E2

Strong base, strong nucleophile, SECOND DEGREE

3:1 E2:SN2

Strong base, strong nucleophile, FIRST DEGREE

1:3 E2:SN2

Weak base, strong nucleophile, FIRST DEGREE

SN2

Weak base, strong nucleophile, SECOND DEGREE

SN2

Weak base, strong nucleophile, THIRD DEGREE

SN1

Weak base, weak nucleophile, THIRD DEGREE

50/50 SN1/E1 ratio

Weak base, weak nucleophile, SECOND DEGREE

NO REACTION

Weak base, weak nucleophile, FIRST DEGREE

NO REACTION

NaH

Strong base, weak nucleophile

DBN (1,5-diazabicylco[4.3.0]non-5-ene)

Strong base, weak nucleophile

DBU (1,5-diazabicyclo[5.4.0]undec-7-ene)

Strong base, weak nucleophile

HO-

Strong base, strong nucleophile

MeO-

Strong base, strong nucleophile

EtO-

Strong base, strong nucleophile

I-

Weak base, strong nucleophile

Br-

Weak base, strong nucleophile

Cl-

Weak base, strong nucleophile

RS-

Weak base, strong nucleophile

HS-

Weak base, strong nucleophile

RSH

Weak base, strong nucleophile

H2S

Weak base, strong nucleophile

H2O

Weak base, weak nucleophile

MeOH

Weak base, weak nucleophile

EtOH

Weak base, weak nucleophile

First degree

Attached carbon is also attached to 1 other CARBON

Second degree

Attached carbon is also attached to 2 other CARBONS

Third degree

Attached carbon is also attached to 3 other CARBONS

Alpha position

Carbon atom connected directly to the halogen

Beta position

Carbon atoms connected to the alpha position

Protic

Contain a hydrogen atom connected directly to an electronegative atom

Polar aprotic

Polar but nevertheless lacks hydrogen atoms connected directly to an electronegative atom

Regioselective

A reaction that can produce two or more constitutional isomers but nevertheless produces one as the major product

The more substituted product (alkene) of an ELIMINATION reaction

Zaitsev product

The less substituted product (alkene) of an ELIMINATION reaction

Hofmann product

Elimination reaction

A reaction involving the loss of a leaving group and formation of a pi (double) bond

Stereospecific

The substrate is stereoisomeric and results in one stereoisomer as the product

Stereoselective

The substrate can produce two isomers as products, where one is the major product

Substitution reaction

Requires the loss of a leaving group AND a nucleophilic attack

2 main reasons why alkyl halides undergo substitution and elimination reactions

The halogen is (1) ELECTRON-WITHDRAWING, and (2) ACTS AS A LEAVING GROUP