Ochem 345 Addition And Elimination

Front 1

pi and sigma bond
which is stronger?

Back 1

sigma bond

Front 2

additio of protic acid (H+) to an alkene occurs such that the proton attaches to th carbon atom w/ akyl group producing mst stable carbocation. (proton will be added to he carbon w the greatest # of hydrogen)

Back 2

markovnikov rule

Front 3

ROOR

Back 3

peroxides

Front 4

H2SO4

strong or week acid?

Back 4

strong acid

Front 5

alcohol and strong acid like H2SO4 lead to?

Back 5

elimination rxn

Front 6

DMSO is protic or aprotic?

Back 6

aprotic

Front 7

X is added to least substituted carbon of double bond. free radical additon occurs when peroxides, oxygen, uv light or other adicalcusing codtion are present

Back 7

antimarkovnikov addition

Front 8

X2 (halogen like Br or Cl)to alkene

Back 8

anti addition of halogens

alkene to alkane

Front 9

NH2-

Back 9

strong base

Front 10

H2/Pt

Back 10

alkene or alkyne to alkane in syn addition of H2

Front 11

alkene or alkyne to alkane in syn addition of H2

Back 11

H2/Pt

Front 12

H2, Pd/BaSO4 and quinline (lindlar's catalyst)

Back 12

alkyne to cis alkene
2 butyne to cis 2 butene

Front 13

alkyne to cis alkene
2 butyne to cis 2 butene

Back 13

H2, Pd/BaSO4 and quinline (lindlar's catalyst)

Front 14

Na, NH3 (liq)

Back 14

alkyne to trans alkene

2 butyne to trans 2 butene

Front 15

alkyne to trans alkene

2 butyne to trans 2 butene

Back 15

Na, NH3 (liq)

Front 16

primary halide (CCOH) favors

Back 16

SN2

Front 17

second and third halide favors

Back 17

E2 rxn due to steric hinderance

Front 18

inc in temp also favors ??

Back 18

elimination over substitution

b/c more bonds are broken and formed in elimination and inc temp inc rate

Front 19

strong and bulky base is favored in

Back 19

E2 rxn

Front 20

large pka =

Back 20

dec acidity = inc in base (stronger the base)

Front 21

E2 rxn favors most or lest substitutted double bond

Back 21

most subsitutted

Front 22

alkyl halides to dehydrogenation, you often get multiple product
double with most sub and lest sub molecule

Back 22

zaitsev's rule

Front 23

more stable base such as ethoxide ion when dehydrogenation you often get more stable double bond molecule whichis

Back 23

most substituted =more stable

Front 24

bulky bse favors more or less sub double bond molecule?

Back 24

less sub

Front 25

when elimination yield the less substituted alkene we say that it followed

Back 25

hoffmann rule

Front 26

the overal relative ease with which alcohols undergo dehydration ?

Back 26

tertiary alcohol>secondary alcohol> primary alcohol

Front 27

in radical rxn, Br is more () than Cl

Cl is mor () than Cr

Back 27

selective (make more stable form)

reacive (mixture of stable and nonstable form)

Front 28

HA / Heat

Back 28

from alcohol to alkene

favored in high temp

most commonly used acds are bronsted lowery acid proton donor

tert alcohol> second alcohol> primary alcohol

tert most reactive

Front 29

used to identify which functional group sare present in a molcule

ony tell what type of bonds are present. NOT HOW MANY

Back 29

IR spectroscopy

Front 30

in IR spectroscopy, methanol and ethanol are distinguishable or indistinguishable

Back 30

indistinguishable

Front 31

1750 cm-1

Back 31

carbonyl C=O

Front 32

alcohol

Back 32

braod 3000 cm-1 (approx)

Front 33

carbonyl C=O

Back 33

1750 cm-1

Front 34

braod 3000 cm-1 (approx)

Back 34

alcohol

Front 35

sharp 3000 cm-1

Back 35

amine N-H

Front 36

amine N-H

Back 36

sharp 3000 cm-1

Front 37

peak at 2800-3500

Back 37

acid, alcohol broad peak above 3000

amine sharp peak above 3000

alkane sharp peak below 3000

Front 38

peak at 1750

Back 38

carbonyl peak
-ketone
aldehyde
caroxylic acid
acid anhydrides
acid halides
aides
ester

Front 39

carbonyl peak
-ketone
aldehyde
caroxylic acid
acid anhydrides
acid halides
aides
ester

Back 39

peak at 1750

Front 40

NMR stands for?

Back 40

nuclear magnetic resonance

Front 41

determine exact molecular structure

Back 41

NMR

Front 42

methane and benzene produce how many NMR signal?

Back 42

one

Front 43

how many sinal chorobenzene produce?

Back 43

three

size of the signal corresponds to the number of the H.

Front 44

chlorocyclohexane produce how many signal?

Back 44

7 signal
you will see fuzzy blob instead of seven distinct peak

Front 45

deshielding
downfield
bing inproximity to e- withdrawing functional group
inc value of sigma

Back 45

means left on a NMR

Front 46

SP3 carbon shows up in the what side of NMR

Back 46

right

Front 47

SP2 carbon shows up in the which side of NMR

Back 47

left
SP2 carbon (C=C or C=O)

Front 48

carboxylic acid in NMR

Back 48

10-12 (left side of NMR)

Front 49

aromatic H is in NMR

Back 49

around 6-7

Front 50

use light of shorter wavelength higher frequency and higher energy than IR

Back 50

UV visable spectrosocpy

Front 51

use to examine conjugated system

Back 51

UV visable spectrosocpy

Front 52

detect mass/mass ratio
molecular ion peaks quivalent to te molecular weight of the molecule

Back 52

mass spectroscopy

Front 53

benzene to benzene-X

halogenation

Back 53

X2/FeX2

Front 54

X2/FeX2

Back 54

bezene to benzne-X

halogenation

Front 55

benzene to benzene-NO2

nitration

Back 55

HNO3 (conc) /H2SO4 (conc)

Front 56

HNO3 (conc) /H2SO4 (conc)

Back 56

benzene to benzene-NO2

nitration

Front 57

benzene to benzene-SO3H

sulfonation

Back 57

H2SO4 (fuming)

Front 58

H2SO4 (fuming)

Back 58

benzene to benzene-SO3H

sulfonation

Front 59

benzene to benzene-R

friedel crafts alkylation

Back 59

RX/AlCl3

Front 60

RX/AlCl3

Back 60

benzene to benzene-R

friedel crafts alkylation

Front 61

benzene to benzene-C=O-R

friedel crafts acylation

Back 61

RCOCl/AlCl3

Front 62

RCOCl/AlCl3

Back 62

benzene to benzene-C=O-R

friedel crafts acylation

Front 63

-NR2
-OH
-OR
-R

Back 63

Ring Activator(more reactive)
e- donating group


Para and orto
but chose para over ortho

Front 64

Ring Activator(more reactive)
e-donating group


Para and orto
but chose para over ortho

Back 64

-NR2
-OH
-OR
-R

Front 65

ring deactivator(less reactive)

ortho and para director

Back 65

-X (halogens)
i.e Bl, Cl

Front 66

-X (halogens)
i.e Bl, Cl

Back 66

ring deactivator(less reactive)

ortho and para director

Front 67

more e donating(activator) is

Back 67

basic

Front 68

more e withdrawing (deactivator) is

Back 68

acidic

Front 69

ring deactivator(less reactive)

meta director

Back 69

-NR3+
-NO2
-CN
-SO3H
-COR, CO2R

Front 70

-NR3+
-NO2
-CN
-SO3H
-COR, CO2R

Back 70

ring deactivator(less reactive)

meta director

Front 71

PCC

Back 71

alcohol to aldehyde(or to ketone if alcholis 2endary)

Front 72

tollen's reagent

Back 72

aldehyde to carboxylic acid

Front 73

KMnO4

Back 73

alcohol to carboxylic acid

Front 74

K2Cr2O7

Back 74

alcohol to carboxylic acid

Front 75

alcohol to aldehyde

Back 75

PCC

Front 76

aldehyde to carboxylic acid

Back 76

tollen's reagent

Front 77

alcohol to carboxylic acid

Back 77

KMnO4

Front 78

alcohol to carboxylic acid

Back 78

K2Cr2O7

Front 79

primary alcohol when oxidize become

Back 79

aldehyde and carboxylic acid
depending on the agent

Front 80

secondary alcohol when oxidize become

Back 80

ketone

Front 81

tertiary alcohol oxidize?

Back 81

do not oxidize

Front 82

1. KMnO4, OH-
2. H+

Back 82

alkene to 2 carboxylic acid

Front 83

1. O3, CH2Cl2
2. Zn/H2O

Back 83

alkene to 2 aldehyde

Front 84

alkene to 2 carboxylic acid

Back 84

1. KMnO4, OH-
2. H+

Front 85

alkene to 2 aldehyde

Back 85

1. O3, CH2Cl2
2. Zn/H2O

Front 86

terminal alkene CHC=CH2 to
carboxylic acid and CO2

Back 86

1. KMnO4 OH- heat
2. H+

Front 87

NaBH4

Back 87

aldehyde and ketone to alcohol

Front 88

LiAlH4 (LAH)

Back 88

aldehyde, ketone, ester, carboxylic acid

to

alcohol

Front 89

aldehyde and ketone to alcohol

Back 89

NaBH4

Front 90

LiAlH4 (LAH)

Back 90

aldehyde, ketone, ester, carboxylic acid

to

alcohol

Front 91

grignard rxn

Back 91

RMgX

Front 92

RMgX (grignard rxn)

Back 92

aldehyde or ketnone to alcohol by adding R-

Front 93

william ether synthesis

Back 93

R-O- Na+ and R-x

to

R-O-R + X- + Na-

Front 94

acyl halide formation

Back 94

carboxylic acid + SOCl2

to

R-C=O-Cl

Front 95

more acidity

Back 95

more e- withdrawing group

Front 96

more basic

Back 96

more e-donating group

Front 97

zaitsev's rule

Back 97

alkyl halides to dehydrogenation, you often have yield containing more than one product

more substituted and less substituted alkene

more substituted is stable

Front 98

alkyl halides to dehydrogenation, you often have yield containing more than one product

more substituted and less substituted alkene

more substituted is stable

Back 98

zaitsev's rule

Front 99

when elimination yield the less substituted alkene we sa that it fllowe the ?

Back 99

hoffman rule

Front 100

hoffman rule

Back 100

when elimination yield the less substituted alkene

Front 101

E2 bimolecular elmination follow wich rule

Back 101

both zaitsev's rule and hoffman's rule

Front 102

E1 unimolecular emlimination follow

Back 102

only saitsev's rule

Front 103

cold dilute KMnO4

Back 103

alkene to alcohol

Front 104

O3, CH2Cl2/NaBH4, CH3OH

Back 104

alkene to alcohol

Front 105

creation of long high molecular weight chains composed of repeating subunit

Back 105

polymerization

Front 106

polymerization occur thru

Back 106

radical mechanism

Front 107

O3, CCl4/ H20

Back 107

alkyne to carboxylic acid

Front 108

naphthalene

Back 108

2 benzene connected together

Front 109

anthracene

Back 109

3 benezene connected together

Front 110

pyridine

Back 110

benzene with N instead of one carbon

Front 111

pyrrole

Back 111

cyclopentane with N instead of one Carbon

Front 112

anisole

Back 112

benzene-OCH3

Front 113

aniline

Back 113

benzene-NH2

Front 114

tolune

Back 114

benzene-CH3

Front 115

phenol

Back 115

benzene-OH

Front 116

CrO3

Back 116

CrO3

Front 117

CrO3

Back 117

CrO3

Front 118

CrO3 (jones reagent)

Back 118

alcohol to carboxyolic acid

if secondary alcohol then to ketone

Front 119

tollens' reagent

Back 119

Ag2O

Front 120

Wolff kishner (H2NNH2)

Back 120

both aldehydes and ketones can be fully reduced to alkanes

Front 121

clemmensem Hg(zn)/HCl

Back 121

both aldehydes and ketones can be fully reduced to alkanes

Front 122

both aldehydes and ketones can be fully reduced to alkanes

Back 122

clemmensem Hg(zn)/HCl

Wolff kishner (H2NNH2)

Front 123

Wolff kishner

Back 123

(H2NNH2)

Front 124

(H2NNH2)

Back 124

Wolff kishner

Front 125

clemmensem Hg(zn)/HCl

Back 125

Hg(zn)/HCl

Front 126

Hg(zn)/HCl

Back 126

clemmensem

Front 127

carboxylic acid to acyl halides

Back 127

SOCl2/H+

Front 128

carboxylic acid to amides

Back 128

NH3