Ch 6 & 7: Haloalkane Reactions (Nucleophilic Substitution and Elimination)

Question 1

Steric Hindrance

Answer 1

Can’t be SN2

Question 2

1st Degree Carbon

Answer 2

Can’t be SN1 or E1

Question 3

3rd Degree Carbon

Answer 3

Can’t be SN2

Question 4

Not an Alkyl Halide

Answer 4

No Reaction

Question 5

Charged Nucleophile

Answer 5

SN2 or E2

Question 6

Neutral Nucleophile

Answer 6

SN1 or E1

Question 7

Protic Solvent

Answer 7

Elimination (only when between SN2 and E2)

Question 8

Aprotic Solvent

Answer 8

Substitution (only when between SN2 and E2)

Question 9

Heat added

Answer 9

Elimination (only when between SN1 and E1)

Question 10

What is a Protic Solvent

Answer 10

A solvent that contains -OH or -NH

Question 11

Sterically Hindered, Strongly Basic Nucleophile

Answer 11

E2

Question 12

Base weaker than OH- with a 3rd Degree Substrate

Answer 12

SN1

Question 13

Base weaker than OH- with a 1st or 2nd Degree Substrate

Answer 13

SN2

Question 14

Weakly Basic Nucleophile

Answer 14

Substitution

Question 15

Unhindered, Strongly Basic Nucleophile with CH3 or a 1st Degree Substrate at Low Temp

Answer 15

SN2

Question 16

What is a Nucleophile?

Answer 16

An electron donor

Question 17

What is an Electrophile?

Answer 17

An electron acceptor

Question 18

What kind of displacement is SN2?

Answer 18

Backside

Question 19

What factors increase Nucleophilic Ability?

Answer 19

Electronegativity of the Nucleophilic Atom, Negative Charge of the Nucleophile, and Basicity of the Nucleophile

Question 20

Order the Nucleophilicity of the Halogens in Protic Solvents from greatest to least

Answer 20

I, Br, Cl, F

Question 21

Order the Nucleophilicity of the Halogens in Aprotic Solvents from greatest to least

Answer 21

F, Cl, Br, I

Question 22

Order the degree of Carbocations from most to least stable

Answer 22

3, 2, 1, 0 (CH3)

Question 23

What kind of displacement is SN1?

Answer 23

Both Frontside and Backside

Question 24

How does Carbocation Stability affect SN1 Reaction Rate?

Answer 24

More stability = Faster reaction

Question 25

What are the best SN1 Leaving Groups?

Answer 25

-OSO2R and MsO- bc of their ability to H-bond with protic solvents

Question 26

Order the Leaving Group Ability of the Halogens in SN1 Reactions from greatest to least

Answer 26

I, Br, Cl, F

Question 27

How does Nucleophilicity affect SN1 Reaction Rate?

Answer 27

The nucleophile doesn’t affect the rate of SN1 reactions

Question 28

What in an SN1 reaction depends on Nucleophilicity?

Answer 28

The distribution of products

Question 29

What type of solvents increase SN1 Reaction Rates?

Answer 29

Protic

Question 30

What types of bases make better Leaving Groups?

Answer 30

Weaker bases

Question 31

What is Zaitsev’s Rule?

Answer 31

In a Haloalkane Elimination, the more substituted product is the Major Organic Product

Question 32

What occurs during the E2 Transition State?

Answer 32

Deprotonation of the base, Departure of the leaving group, and Rehybridization of the Cs to sp2

Question 33

What does the Reaction Rate of E2 depend on?

Answer 33

Concentration of the base and substrate

Question 34

What does the Reaction Rate of E2 depend on?

Answer 34

Concentration of the base and substrate

Question 34

What does the Reaction Rate of E2 depend on?

Answer 34

Concentration of the base and substrate