Ch. 4: Analyzing Organic Reactions

Question 1

an acid-base reaction will proceed so long as what is more reactive than what

Answer 1

as long as reactants are more reactive/stronger than the products

Question 2

Lewis acids are electron…

Answer 2

electron acceptors in the formation of a covalent bond. Tend to be electrophiles

Question 3

Lewis bases are electron…

Answer 3

electron donors in the formation of a covalent bond. Tend to be nucleophiles.

Question 4

lewis acids and bases form what kind of covalent bonds

Answer 4

coordinate covalent bonds, in which both electrons come from the same starting atom (the Lewis acid)

Question 5

amphoteric

Answer 5

ability to act as either Bronsted-Lowry acids or bases

Question 6

Bronsted-Lowry acids are proton…

Answer 6

proton donors (H+)

Question 7

Bronsted-Lowry bases are proton…

Answer 7

acceptors

Question 8

acid dissociation constant, Ka, measures

Answer 8

strength of an acid in solution

Question 9

Ka = …

Answer 9

Ka = [H+][A-] / [HA]

Question 10

pKa = …

Answer 10

-log Ka

Question 11

acidic molecules have what size pKa

Answer 11

small, even negative

Question 12

basic molecules have what size pKa

Answer 12

large

Question 13

effect of charge on nucleophile strength

Answer 13

increases with increased electron density/increased negative charge

Question 14

effect of electronegativity on nucleophilic strength

Answer 14

decreases as EN increases

Question 15

effect of steric hindrance on nucleophilic strength

Answer 15

decreases as molecules become bulky

Question 16

effect of solvent on nucleophilic strength

Answer 16

decreases in protic solvents

Question 17

common nucleophiles

Answer 17

HONC with a minus sign or lone pair

Question 18

In a polar protic solvent, nucleophilicity increases up/down the periodic table?

Answer 18

increases down the periodic table because down the periodic table are less effected by the protons in solution

I- > Br- > Cl- > F-

Question 19

In a polar aprotic solvent, nucleophilicity increases up/down the periodic table?

Answer 19

increases up the periodic table because no protons are in the way of attacking the nucleophile

F- > Cl- > Br- > I-

Question 20

nucleophiles are attracted to…?

Answer 20

nucleus (positive areas of charge) because they are electron/negative charge rich

Question 21

electrophiles are attracted to…?

Answer 21

electrons (negative areas of charge) because they are positive charge rich

Question 22

common electrophiles

Answer 22

alcohols, aldehydes and ketones, carboxylic acids (electrophilicity is essentially acidity)

Question 23

Heterolytic reactions

Answer 23

a bond is broken and both electrons are given to one of the two products

Question 24

term for which molecular fragment retains electrons after heterolysis

Answer 24

leaving group

Question 25

what makes for a good leaving group

Answer 25

leaving group will stabilize the extra electrons

I-, Br-, Cl-

Question 26

SN1 reactions have how many steps

Answer 26

two

1. leaving group leaves, generating a carbocation
2. nucleophile attacks the carbocation

SUBSTITUTION PRODUCT

Question 27

Which step of an SN1 reaction is the rate limiting step

Answer 27

step one, the leaving group leaves

Question 28

SN2 reactions have how many steps

Answer 28

one step

nucleophile attacks the compound at the same time the leaving group leaves

Question 29

what changes in oxidation-reduction reactions

Answer 29

the oxidation states of the reactants

Question 30

oxidation

Answer 30

increase in oxidation state,

loss of electrons OR decrease in number of bonds to hydrogen and increase in number of bonds to carbon, nitrogen, oxygen, halides

Question 31

reduction

Answer 31

decrease in oxidation state, gain of electrons or number of bonds to hydrogen

Question 32

oxidizing agent

Answer 32

element/compound that accepts electron from another species during a redox reaction

Question 33

what does it mean to be “reduced”

Answer 33

to accept electrons during an redox reaction, to be an oxidizing agent

Question 34

oxidizing agents usually contain metals bonded to a large number of what kind of atoms

Answer 34

oxygen atoms

Question 35

reduction agents usually contain metals bonded to a large number of what kind of atoms

Answer 35

hydrides