Chapter 9.3: Experimental Evidence for SN1 and SN2 Mechanisms

Question 1

What is a solvent that cannot serve as a hydrogen-bond donor; nowhere in the molecule is there a hydrogen bonded to an atom of high electronegativity?

Answer 1

aprotic solvents

Question 2

Define benzylic carbocations

Answer 2

a carbocation in which a carbon attached to a benzene ring bears the positive charge

Question 3

Define protic solvents

Answer 3

a solvent that is a hydrogen-bond donor

Question 4

What is a carbocation in which an allylic carbon bears the positive charge?

Answer 4

allylic carbocations

Question 5

What is a carbocation in which a carbon attached to a benzene ring bears the positive charge?

Answer 5

benzylic carbocations

Question 6

Define nucleophilicity

Answer 6

a kinetic property measured by the rate at which a nucleophile causes nucleophilic substitution on a reference compound under a standardized set of experimental conditions

Question 7

Define basicity

Answer 7

an equilibrium property measured by the position of equilibrium in an acid-base reaction

Question 8

Define dielectric constant

Answer 8

a measure of a solvent’s ability to insulate opposite charges from one another

Question 9

Define allylic carbocations

Answer 9

a carbocation in which an allylic carbon bears the positive charge

Question 10

What is an equilibrium property measured by the position of equilibrium in an acid-base reaction?

Answer 10

basicity

Question 11

What is a solvent that is a hydrogen-bond donor?

Answer 11

protic solvents

Question 12

What means next to a carbon-carbon double bond?

Answer 12

allylic

Question 13

What is a measure of a solvent’s ability to insulate opposite charges from one another?

Answer 13

dielectric constant

Question 14

Define allylic

Answer 14

next to a carbon-carbon double bond

Question 15

What is a kinetic property measured by the rate at which a nucleophile causes nucleophilic substitution on a reference compound under a standardized set of experimental conditions?

Answer 15

nucleophilicity

Question 16

Define steric hindrance

Answer 16

the ability of groups, because of their size, to hinder access to a reaction site within a molecule

Question 17

Define aprotic solvents

Answer 17

a solvent that cannot serve as a hydrogen-bond donor; nowhere in the molecule is there a hydrogen bonded to an atom of high electronegativity

Question 18

What is the ability of groups, because of their size, to hinder access to a reaction site within a molecule?

Answer 18

steric hindrance