Chapter 4

Question 1

Lewis acid

Answer 1

electron acceptors

vacant orbitals or positively polarized atoms

Question 2

Lewis base

Answer 2

electron donors

have lone pair of electrons and are often anions

Question 3

Bronsted Lowry Acid

Answer 3

Proton donor

Question 4

Bronsted Lowry Base

Answer 4

Proton acceptor

Question 5

Amphoteric

Answer 5

can act as acid or base depending on reaction conditions

Question 6

Acid dissociation constant

Answer 6

Ka

Measure of acidity and corresponds to dissociation of an acid into proton and conjugate base

Question 7

pKa

Answer 7

-log(Ka)

Lower pKa is stronger acid

Question 8

How does pKa trend on a periodic table

Answer 8

decreases down the table and as EN increases

Question 9

Common basic functional groups

Answer 9

amines and amides

Question 10

Common acidic functional groups

Answer 10

alcohols, aldehydes, ketones, carboxylic acids, and acid derivatives

Question 11

nucleophiles

Answer 11

nucleus loving, contain lone pairs or pi bonds

have increased electron density and often carry a negative charge

more basic is better nucleophile

Question 12

How do nucleophile properties differ from bases

Answer 12

Nucleophilicity is kinetic, basicity is thermodynamic

Question 13

What affects nucleophilicity

Answer 13

Charge, electronegativity, sterics, solvent

Question 14

Electrophiles

Answer 14

electron loving, have positive charged or positively polarized

Question 15

What normally acts as a good electrophile

Answer 15

alcohols, aldehydes, ketones, carboxylic acids, and acid derivatives

Question 16

Leaving groups

Answer 16

molecular fragments that contain electrons after heterolysis

Question 17

What makes a good leaving groups

Answer 17

groups that can stabilize charges through resonance or induction

weak bases

Question 18

SN1 reaction

Answer 18

unimolecular nucleophilic substitution

LG leaves forming carbocation

Nucleophilic attacks cation

Question 19

What is the product of SN1

Answer 19

racemic mixture of product (can attack from either side)

Question 20

What type of carbons are preferred for SN1

Answer 20

more substituted carbons because the alkyl groups are EDG which stabilizes the positive carbocation

Question 21

Rate of SN1

Answer 21

depends only on concentration of substrate

rate= k [R-L]

Question 22

SN2 reaction

Answer 22

bimolecular nucleophilic substitution

nucleophile attacks while LG leaves ONE STEP

Question 23

What is the product of SN2 reactions

Answer 23

Inverted stereochemistry product due to the backside attack

Question 24

What is preferred for SN2 reaction

Answer 24

less substituted carbon because the steric hindrance affects the nucleophile from accessing the electrophilic substrate

Question 25

Rate of SN2 reaction

Answer 25

depends on concentration of nucleophile and substrate

rate=k [nu][R-L]

Question 26

Oxidation state

Answer 26

charge an atom would have if all bonds were completely ionic

CH4 lowest oxidation (most reduced) CO2 is highest

Question 27

Rank oxidation of functional groups

Answer 27

Carboxylic acids/ derivatives> aldehydes > ketones > imines> alcohols > alkyl halides > amines

Question 28

oxidation

Answer 28

increase in oxidation state and is assisted by oxidation agents

more bonds to O, less to H

Question 29

Oxidation agents

Answer 29

Accept electrons, are reduced

High electron affinity, high oxidation state

Contain a metal and many oxygens

Question 30

PCC

Answer 30

alcohol to aldehyde

Question 31

What oxidizes alcohol to Carboxylic acid

Answer 31

CrO3 or Na2Cr2O7

Question 32

Reduction

Answer 32

decrease in oxidation sate and is assisted by reducing agents

Question 33

Reducing agents

Answer 33

donate electrons and are oxidized

low EN low ionization energy

contain metal and many hydrides

Question 34

LiAlH4

Answer 34

Reduces aldehydes, ketones, and carboxylic acids to alcohols

Amides to amines

esters to alcohol