Organic Chemistry

Front 1

HBr

Back 1

What Reagent?

Front 2

In a Williamson ether synthesis
1)what kind of molecule is made in the first step?
2)How is it made?

Back 2

1) Alkoxide
2) Adding an alcohol to Na, K, or NaH

Front 3

In a Williamson Ether Synthesis, what occurs if a secondary halide or tosylate is used?

Back 3

Creates a possibility for an E2 Reaction to occur, which competes with the desired SN2, reaction usually sucks.

Front 4

What does MCPBA do as a reagent?

Back 4

Breaks an Alkene into an epoxide.

Front 5

1)What kind of substance is MCPBA and CH3COOOH?
2)What do they do as reagents?

Back 5

1)Peracids
2)Break alkenes into epoxides

Front 6

What does CH3COOOH do as a reagent?

Back 6

Breaks an Alkene into an epoxide

Front 7

What Product?

Back 7

.

Front 8

HI

Back 8

What Reagent?

Front 9

What Reagent?

Back 9

.

Front 10

What Product?

Back 10

.

Front 11

What Product?

Back 11

.

Front 12

What hybridization are all carbons in a benzene ring?

Back 12

sp2

Front 13

1)What bond angle are all carbons in a benzene ring?
2)What shape does the ring take because of this?

Back 13

1)120
2)Flat

Front 14

What is the molecular mass of benzene?

Back 14

78

Front 15

Is a double bond or single bond longer?

Back 15

Single

Front 16

What bonds are longer in a benzene ring?

Back 16

All benzene bonds stretch to the same size

Front 17

What happens in an aromatic to allow resonance stabilization?

Back 17

P-orbitals line up parallel to allow electrons to move freely from one to the other

Front 18

What is the kekule structure?
What does it symbolize?

Back 18

Constant resonance

Front 19

How stable is benzene? How reactive?

Back 19

Very Stable. Very unreactive.

Front 20

Define Aromaticity

Back 20

High Stability, usually due to resonance stabalization

Front 21

How do you determine if a molecule is aromatic?

Back 21

1)Cyclic
2)Planar compound - must have all atoms in ring in sp2 hybridization
3)Must have Huckel # of pi electrons

Front 22

What is the Huckel Rule?

Back 22

In order to be aromatic the ring must have 4n+2 pi electrons where n=0,1,2...

Front 23

What are the first four Huckel Numbers?

Back 23

2,6,10,14...

Front 24

How do you know if a compound is anti-aromatic?

Back 24

Must be cyclic and planar, but no huckel number of pi electrons exists. Has 4n Pi electrons

Front 25

What is a heteroatom?

Back 25

N, O, P, S..

Front 26

What does the atomic number signify in a neutral atom

Back 26

The number of protons in the nucleus and the number of electrons surrounding it

Front 27

What does the mass number signify in a neutral atom

Back 27

Sum of the number of protons and neutrons in nucleus

Front 28

What does the Heisenberg Uncertainty Principle state?

Back 28

The exact location of an electron can never be determined, but the orbital defines where there is a high probability of finding an electron with a certain energy.

Front 29

Explain the arrangement of electron density of a 2s orbital.

Back 29

Has a small region of high electron density close to the nucleus, but most of the electron density is farther from the nucleus, beyond a node, or region of zero electron density.

Front 30

What is the Pauli Exclusion Principle?

Back 30

There are a maximum of 2 electrons in each orbital (spins must be paired)

Front 31

What is the Aufbau Principle?

Back 31

Electrons "build up" the orbitals from lowest energy to highest energy.

Front 32

What is Hund's Rule?

Back 32

Electrons "build up" or "fill" one orbital at a time in a sublevel and then pair.

Front 33

How is the major contributor of a molecule with resonsance determined?

Back 33

1) As many octets as possible
2) As many bonds as possible
3) Any negative charges on the more electronegative atoms
4) As little charge seperation as possible

Front 34

Arrhenius Acid

Back 34

substance that ionizes/dissociates in water to give a hydronium ion

Front 35

Arrhenius base

Back 35

substance that dissociates in water to give a hydroxide ion

Front 36

How is pH calculated?

Back 36

pH = -log[H3O+)

Front 37

Bronsted-Lowry Acid

Back 37

any species that can donate a proton

Front 38

Bronsted-Lowry Base

Back 38

any species that can accept a proton

Front 39

Lewis base

Back 39

an electron pair donor, nucleophile

Front 40

Lewis acid

Back 40

an electron pair acceptor, electrophile

Front 41

degenerate orbitals

Back 41

orbitals with identical energies

Front 42

conjugate acid

Back 42

acid that results from the protonation of a base

Front 43

conjugate base

Back 43

base that results from the deprotonation of an acid

Front 44

constitutional isomers

Back 44

isomers that are connected differently, differing in bonding sequence

Front 45

structural isomers

Back 45

isomers that are connected differently, differing in bonding sequence

Front 46

stereoisomers

Back 46

isomers that differ only in how their atoms are arranged in space

Front 47

cis/trans isomers

Back 47

stereoisomers that differ in their cis-trans arrangement on a ring or a double bond

Front 48

geometric isomers

Back 48

stereoisomers that differ in their cis-trans arrangement on a ring or a double bond

Front 49

axial bond

Back 49

one of six bonds (three up and three down) on the chair conformation of the cyclohexane ring that are parallel to the "axis" of the ring

Front 50

The most stable conformation of cyclohexane

Back 50

Chair conformation

Front 51

cracking

Back 51

heating large alkanes to cleave them into smaller molecules

Front 52

equatorial bond

Back 52

one of the six bonds (three down and three up) on the cyclohexane ring that are directed out toward the "equator" of the ring.

Front 53

spirocyclic conformation

Back 53

bicyclic compounds in which the two rings share only one carbon atom

Front 54

The first propagation step is ____ for bromination but ____ for chlorination.

Back 54

endothermic, exothermic

Front 55

The transition states forming the primary and secondary radicals for the ____ ____ have a larger energy difference than those for the ____ ____.

Back 55

endothermic bromination
exothermic chlorination

Front 56

In a ____ reaction, the transition state is closer to the products in energy and in structure.

Back 56

endothermic

Front 57

In a ____ reaction, the transition state is closer to the reactants in energy and in structure.

Back 57

exothermic

Front 58

Hammond postulate

Back 58

Related species that are closer in energy are also closer in structure. The structure of a transition state resembles the structure of the closest stable species.

Front 59

Name of a benzene with an -OH

Back 59

Phenol

Front 60

Name of a benzene with an -NH2

Back 60

Aniline

Front 61

Name of a benzene with a -CH3

Back 61

Toluene

Front 62

Name of a benzene with an -OCH3

Back 62

Anisole

Front 63

Name of a benzene with a -COOH

Back 63

Benzoic Acid

Front 64

Name of a benzene with a -COH

Back 64

Benzaldehyde

Front 65

What kind of substituent configuration does ortho represent?

Back 65

1,2

Front 66

What kind of substituent configuration does meta represent?

Back 66

1,3

Front 67

What kind of substituent configuration does para represent?

Back 67

1,4

Front 68

What does a benzene ring require to proceed in a substitution reaction?

Back 68

Super strong electrophile

Front 69

What does the halogenation of a benzene require?

Back 69

Lewis acid catalyst

Front 70

What catalyst is required for the chlorination of a benzene?

Back 70

FeCl3 or AlCl3

Front 71

What catalyst is required for the brominatino of a benzene?

Back 71

FeBr3

Front 72

How would you brominate benzene? How would you chlorinate?

Back 72

Br2, FeBr3
Cl2, FeCl3 or AlCl3

Front 73

What hybridization does the reactive carbon have in its intermediate state of an electrophilic aromatic substitution reaction?

Back 73

sp3

Front 74

What hybridization does an aromatic carbon have? What hybridization is the end product of the carbon after electrophilic aromatic substitution?

Back 74

sp2, sp2

Front 75

How do you iodinate an aromatic?

Back 75

I2, HNO3

Front 76

What reagents are required for the nitration of an aromatic?

Back 76

HNO3, H2SO4

Front 77

How does HNO3 and H2SO4 act as reagents to nitrate an aromatic?

Back 77

H2SO4 is a much stronger acid so it donates a proton to the less stronger acid, HNO3. The HNO3 acts as a base and accepts the proton. H2NO3 loses water and NO2 is formed, which reacts in the substitution.

Front 78

What can be used to reduce nitrobenzene to aniline?

Back 78

Zn, Sn.. , HCl

Front 79

How is an aromatic sulfonated?

Back 79

SO3, conc. H2SO4

Front 80

An electron withdrawing substituent on an aromatic ring is:
activating/deactivating
ortho/meta/para director

Back 80

deactivating
meta director

Front 81

An electron donating substituent on an aromatic ring is:
activating/deactivating
ortho/meta/para director

Back 81

activating
ortho/para director

Front 82

A halogen on an aromatic ring is:
activating/deactivating
ortho/meta/para director

Back 82

deactivating
ortho/para director

Front 83

2,4-dimethylpentanol
Structure?

Back 83

Name?

Front 84

cyclohex-3-en-1-ol
Structure?

Back 84

Name?

Front 85

6-bromo-5-methyl-2,3-hexandiol
Structure?

Back 85

Name?

Front 86

It is a general principle that reactions proceed towards ___ reactive species.

Back 86

Less

Front 87

What is the stability of the following starting with the most stable to least stable?

CH3CH2O-
ClCH2CH2O-
CH3O
Cl3CCH2O-

Back 87

Cl3CCH2O-
ClCH2CH2O-
CH3O-
CH3CH2O-

Front 88

What is the reactivity of the following starting with the most reactive to least reactive?

CH3CH2O-
ClCH2CH2O-
CH3O
Cl3CCH2O-

Back 88

CH3CH2O-
CH3O-
ClCH2CH2O-
Cl3CCH2O-

Front 89

3 > 1 > 2

Back 89

Number from most to least stable

Front 90

What product?

Back 90

.

Front 91

Product?

Back 91

.

Front 92

What reagent(s)?

Back 92

.

Front 93

What starting material?

Back 93

.

Front 94

What product?

Back 94

.

Front 95

What reagents?

Back 95

.

Front 96

What starting material?

Back 96

.

Front 97

What product is formed when combining a grignard reagent and an aldehyde?

Back 97

Secondary alcohol

Front 98

What product is formed when combining a grignard reagent and a ketone?

Back 98

Tertiary alcohol

Front 99

What product is formed when combining a grignard reagent and formaldehyde?

Back 99

Primary alcohol

Front 100

What product?

Back 100

.

Front 101

What reagents?

Back 101

.

Front 102

What starting material?

Back 102

.

Front 103

What product?

Back 103

.

Front 104

What product?

Back 104

.

Front 105

In order to get a tertiary alcohol from a grignard reagent and an acid chloride, what must occur?

Back 105

Grignard reagent must react twice with the acid chloride.

Front 106

In order to get a tertiary alcohol from a grignard reagent and an ester, what must occur?

Back 106

Grignard reagent must react twice with the ester.

Front 107

What kind of product(s) are formed when a grignard reagent is reacted with an ester?

Back 107

A tertiary alcohol and a primary alcohol

Front 108

What product?

Back 108

.

Front 109

What reagents?

Back 109

.

Front 110

What starting material?

Back 110

.

Front 111

What product?

Back 111

.

Front 112

What reagents?

Back 112

.

Front 113

What starting material?

Back 113

.

Front 114

Synthesize with:

a)grignard reagent and a carbonyl.
b)organolithium and a carbonyl
c)grignard reagent and acid chloride

Back 114

.

Front 115

Synthesize.

Back 115

.

Front 116

Synthesize with:
a)Grignard reagent (2 ways)
b)Organolithium

Back 116

.

Front 117

1)Grignard chemistry will not work with a molecule with these functional group(s).
2)This will happen instead of the grignard reaction
3)This happens because

Back 117

1) Hydroxyl, sulfhydryl, -NH
2) Acid/Base reaction. The Reactive group from the grignard reagent will remove the H from the acidic O, S, or N, and the acidic atom that lost the proton will bond with the organometallic.
3)It takes less energy

Front 118

Define Oxidation

Back 118

Addition of O content or removal of H

Front 119

Define Reduction

Back 119

Addition of H content or removal of O

Front 120

When a molecule is in its most oxidized state it is ____ to reduce.

Back 120

difficult

Front 121

If you wanted to reduce a ketone or aldehyde what could you use?

Back 121

LAH or NaBH4

Front 122

If you wanted to reduce a carboxylic acid what could you use?

Back 122

LAH