Orgo Ii Exam 1

Front 1

Structure of Benzene

Back 1

Equal angles of 120

Equal C-C bond lengths

Equal C-H bond lengths

Resonance structures equal

Front 2

Conjugation is _____ stable than isolation.

Back 2

More

Front 3

O substitution

Back 3

Front 4

M substituted

Back 4

Front 5

P substituted

Back 5

Front 6

Name

Back 6

Benzaldehyde

Front 7

Name

Back 7

Benzoic Acid

Front 8

Name

Back 8

Styrene

Front 9

Name

Back 9

Acetophenone

Front 10

Name

Back 10

Phenol

Front 11

Name

Back 11

Anisole

Front 12

Name

Back 12

Aniline

Front 13

What reaction is shown?

Back 13

SN1 of the benzylic halides

Front 14

What reaction is shown?

Back 14

Sn2 of the Benzylic Halides

Front 15

Back 15

Can become radicals like allylic, more stable

Front 16

What reaction is shown?

Back 16

Benzylic free radical with NBS

Front 17

What reaction is shown?

Back 17

Polymerization of styrene

Front 18

Huckel's Rule

Back 18

Aromatic = (4n+2) = pi electrons

Antiaromatic = (4n) = pi electrons

Front 19

Completely conjugated rings with more than 6 carbons.

Back 19

Annulenes

Front 20

Can ions be aromatic?

Back 20

Yes

Front 21

Back 21

Directly attached, benzene group called "phenyl"

Front 22

What reactions are shown?

Back 22

Oxidation at the Benzylic position

Front 23

What reaction is shown?

Back 23

Nitration

Front 24

What reaction is shown?

Back 24

Sulfonation

Front 25

What reaction is shown?

Back 25

Halogenation

Front 26

What reaction is shown below?

Back 26

Iodination

Front 27

What reaction is shown below?

Back 27

Friedel-Crafts Alkylation

Front 28

What reagents are used in Friedel-Crafts Alkylation?

Back 28

A carbon chain attached to a halide and AlCl3.

Front 29

What reaction is shown below?

Back 29

Friedel-Crafts Acylation

Front 30

What reaction is shown below?

Back 30

Clemmensen reduction

Front 31

What reaction is shown below?

Back 31

Wolff-Kishner reduction

Front 32

What is the rate law of SnAR?

Back 32

Second order.

Electron withdrawing groups stabilize.

Electronegative halides increase the rate of anion formation.

Front 33

Nitrobenzene to aniline reactions. What reactants are used?

Back 33

Front 34

What reaction is shown?

Back 34

Nitrosation of Arylamines

Only works with 1° amines

Front 35

Reactions with N2 as a psyeudohalide

Back 35

Front 36

Azo Coupling of Diazonium Salt

Back 36

Front 37

How to name organometallic compounds

Back 37

Front 38

What reaction is shown?

Back 38

Preparation of Organolithium Compounds

Front 39

What reaction is shown?

Back 39

Preparation of organomagnesium compounds

Front 40

What reagents are used to create organometals?

Back 40

Diethyl ether or THF

Front 41

Are organometallic carbons basic or acidic?

Back 41

They are Bronsted bases (accept H)

Front 42

What happens when an organometallic and Gringard reagent react with ketones and aldehydes?

Back 42

Alcohols are formed

Front 43

What mechanism is shown?

Back 43

Addition of organometallic reagents to ketone or aldehyde (to form alcohols)

Front 44

What reaction is shown?

Back 44

Creation of acetylenic alcohols

Front 45

What reaction is shown?

Back 45

Organocuprate (Gilman Reagents) reacting with RX and ARX to make C-C bonds

Inversion of sterochem

Only works with methyl and primary. If secondary or tertiary, E2 occurs

Front 46

What reagents are used for organocuprate reagent reactions?

Back 46

Diethyl ether or THF

Front 47

Memorize

Back 47

Front 48

Review of how alcohols are made:

Back 48

Front 49

What reaction is shown?

Back 49

Metal Catalyzer Hydrogenation of Aldehydes or Ketones

Front 50

What reaction is shown?

Back 50

Lithium aluminum hydride reduction

Works with ketones, Aldehydes, and acyl compounds

Front 51

What kind of reagents are used to reduce ketones and aldehydes to alcohols?

Back 51

LiAlH4 or NaBH4 and H2O

Front 52

What reactions are shown?

Back 52

Sodium Borohydride reduction of Aldehydes or ketones to form alcohols

Front 53

What mechanism is shown?

Back 53

Reduction of aldehydes and ketones to form alcohols, with hydride reagents

Front 54

What mechanism is shown?

Back 54

Lithium aluminum hydride reduction of carboxylic acids to primary alcohol

Front 55

What reagents are used for epoxide ring openings to make alcohols?

Back 55

Gringard reagent (organometallic reagents), 1. diethyl ether, 2. H3O+

Front 56

What reaction is shown?

Back 56

Formation of alcohols from the ring opening of epoxides using organometals (nucleophiles)

Front 57

What mechanism is shown?

Back 57

Ring opening of an epoxide with an organometallic reagent

Front 58

What reaction is shown?

Back 58

Acid catalyzed dialkyl ether formation from PRIMARY alcohols

Front 59

What mechanism is shown?

Back 59

Conversion of alcohols to ethers

Front 60

What reagents are needed for Fischer Esterification?

Back 60

Alcohol, carboxylic acid, and acid catalyst

Front 61

What reaction is shown?

Back 61

Fischer Esterification

Succeeds by employing Le Chat's. Moves H2O to shift equilibrium to the left. Uses Dean-Stark trap (Benzene/H2O azetrope)

Front 62

What reaction is shown?

Back 62

Creation of esters using reactive acyl halides with alcohol

Front 63

What reaction is shown?

Back 63

Oxidation of primary alcohols to carboxylic acids via aldehydes

1° alcohols form carboxy acids

2° alcohols form ketones

3° alcohols do not react

Front 64

What reaction is shown?

Back 64

Oxidation of primary alcohols to aldehydes

Front 65

What reaction is shown?

Back 65

Oxidation of secondary alcohols to ketones

Front 66

What is the mechanism of the oxidation of secondary alcohols using chromate compounds?

Back 66

There is a chromic acid oxidizer which attaches and creates ester. The compound reacts with water and falls apart, which creates oxidized compound (ketone)

Front 67

What reaction is shown?

Back 67

Oxidation of alcohols using Swern conditions

Front 68

In the body, how are alcohols oxidized?

Back 68

NAD+ in alcohol dehydrogenase

Front 69

What reaction is shown?

Back 69

Oxidative cleavage of vicinal diols using HIO4

Front 70

How to name thiols:

Back 70

No H bonding in thiols

Better nucleophiles

Better leaving groups

Stronger acids

Front 71

What reaction is shown?

Back 71

Sn2 using sulfide or thiols

Front 72

Nomenclature of ethers and epoxides

Back 72

Front 73

Nomenclature of sulfides

Back 73

Front 74

What is a crown ether?

Back 74

Front 75

What reaction is shown?

Back 75

Crown ether reaction

Front 76

Reminder of ways to make ethers:

Back 76

Front 77

What reaction is shown?

Back 77

Williamson Ether Synthesis

Front 78

What mechanism is shown?

Back 78

Williamson Ether Synthesis

Front 79

What reaction is shown?

Back 79

Acid catalyzed cleavage of ethers to form alkyl halide

Front 80

What mechanism is shown?

Back 80

Acid catalyzed cleavage of ethers to form alkyl halides

Front 81

What reaction is shown?

Back 81

Birch reduction

Front 82

What reagents are used in the Clemmensen Reduction?

Back 82

Zn(Hg) and HCL

Front 83

What reagents are used in the Wolff-Kishner Reduction

Back 83

H2NNH2, KOH, triethylene glycol, at 175°C

Front 84

Memorize

Back 84

Front 85

What reagents can be used to oxidize the Benzylic position to carboxylic acids?

Back 85

Na2Cr2O7, H2O, H2SO4, heat

Or

1. KMnO4, H2O

2. HCl

Front 86

What reagents are used in the Birch Reduction?

Back 86

Na, NH3, CH3CH2OH

Front 87

Memorize

Back 87

Front 88

Memorize

Back 88

Front 89

Memorize

Back 89

Front 90

What reaction is shown?

Back 90

Nucleophilic aromatic substitution (SnAr)

Second order