substitution and elimination

What are the six common nucleophiles?

I-

Cl-

Br-

HO-

HS-

N triple bond C-

• Don’t need to be dully negative and can be partially rich

What are five common leaving groups?

I-

Cl-

Br-

Sulfuric acid

H₂O

Nuclephiles strength ____ from right to left on a periodic table in oth polar protic solvents and polar aprotic solvents

increases

In a polar protic solvent, nucleophiles strength _____ a group. Why?

Increase down because larger atoms are more polarizable. The larger the atomic radius, the stronger the nucleophile.

What are five common polar protic solvents?

Water, methanol, ethanol, acetic acid, and ammonia

In a polar aprotic solvent, nucleophilicity ____ a group. Why?

decreases up the group due to lack of hydrogen bonding, which allows smaller nucleophiles to be more effective.

What are the four common polar aprotic solvents?

Acetone, DMSO, DMF, and THF

In an elimination reaction, a ___ is formed via the loss of a proton and a leaving group.

Double bond

In substitution reaction, a _____ is replaced with a nucleophile

leaving group

What occurs in a S_N2 reaction?

A nucleophile attacks a substrate, displacing a leaving group in a single concerted step.

Due to S_N2 reactions being concerted, they have a ?

A pentavalent transition state and a bimolecular rate law.

What is a pentavalent transition state?

It consists of the electrophile weakly coordinated to both the nucleophile and the leaving group

In an S_N2, does the nucleophile attack the electrophile from the back or the front? 

Back

S_N2 reactions are stereospecific. If a nucleophile attacks a chiral center, what happens? 

An inversion of stereochemistry occurs. For example if it was R then it will be S

Is S_N1 a one or more step process?

It is a more steps

What is the first step for S_N1 reaction?

It is a carbocation intermediate formation via the loss of a leaving group. This is considered as the rate limiting step of the reaction

What occurs in the second step for S_N1 reaction?

Is a carbocation rearrangement, if possible

What is the final step of S_N1?

It is a nucleophile attack of the carbocation to form the final product.

S_N1 can only occur in what type of substrate?

Only secondary and tertiary substrates are required because they require stable carbocations for the reaction to proceed.

S_N1 reaction is a ___ rate law and does not include the?

Unimolecular rate kaw and does not include the concentration of the nucleophile.

What does the Zaitsev product refer to?

To the more substituted alkene

What does the Hofmann product refer to?

Less substituted alkene