Chem 227 Exam 3

Front 1

ethylene

Back 1

ethene

Front 2

methylene group

Back 2

=CH2 substituent

Front 3

vinyl group

Back 3

H2C=CH- substituent

Front 4

allyl group

Back 4

H2C=CHCH2- substituent

Front 5

propylene

Back 5

propene

Front 6

isobutylene

Back 6

2-methylpropene

Front 7

isoprene

Back 7

2-methyl-1,3-butadiene

Front 8

hyperconjugation

Back 8

an electronic interaction that results from overlap of a vacant p orbital on one atom with a neighboring C-H sigma bond. results when alkenes are substituted.

Front 9

regiospecific

Back 9

only one of two possible orientations of addition occurs

Front 10

Markovnikov's rule

Back 10

in the addition of HX to an alkene, the H adds to the carbon with fewer alkyl substituents and the X attaches to the carbon with more alkyl substituents

Front 11

Hammond postulate

Back 11

states that we can get a picture of what a transition state looks like by looking at the structure of the nearest stable species. exergonic reactions have transition states that resemble reactant; endergonic reactions have transition states that resemble product

Front 12

hydride shift

Back 12

the shift of a hydrogen atom and its electron pair (a hydride ion, H-) between neighboring carbons

Front 13

hypohalous acid

Back 13

any oxyacid of a halogen of general formula HOX

Front 14

epoxide

Back 14

three-membered cyclic ether

Front 15

diol

Back 15

two -OH groups

Front 16

halohydrin

Back 16

OH and X

Front 17

dehydrohalogenation

Back 17

the loss of HX from an alkyl halide

Front 18

dehydration

Back 18

the loss of water from an alcohol

Front 19

halogenation

Back 19

addition of bromine or chlorine to alkenes to produce dihalides

Front 20

halogenation of alkenes always results in cis/trans

Back 20

trans

Front 21

anti stereochemistry

Back 21

adds on opposite faces of double bond

Front 22

bromonium/chloronium ion

Back 22

R2Br+ or R2Cl2, intermediate formed in halogenation of alkenes, looks like a triangle

Front 23

NBS/DMSO results in

Back 23

halohydrin

Front 24

X2/H2O results in

Back 24

halohydrin

Front 25

hydration

Back 25

when water adds to alkenes to form alcohols

Front 26

protonated alcohol

Back 26

has -H2O+

Front 27

oxymercuration/demercuration 2 steps

Back 27

1. Hg(OAc)2, H2O/THF
2. NaBH4

Front 28

oxymercuration/demercuration results in

Back 28

an alcohol

Front 29

mercurinium ion is the intermediate in

Back 29

demercuration

Front 30

in oxymercuration, the -OH attaches to the

Back 30

more highly substituted carbon (Markovinikov)

Front 31

the second intermediate in oxymercuration/demercuration

Back 31

an organomercury compound (-OH and -Hg(OAc) on opposite sides of what used to be double bond)

Front 32

used for demercuration

Back 32

NaBH4

Front 33

hydroboration

Back 33

addition of B-H bond in BH3 in THF solvent to alkene

Front 34

hydroboration results in

Back 34

organoborane intermediate, BH2 and H added to alkene

Front 35

what follows hydroboration

Back 35

oxidation with H2O2 in a basic solution which yields an alcohol

Front 36

hydroboration is Markovnikov or non

Back 36

non-Markovnikov

Front 37

BH3-THF reacts with alkenes to form

Back 37

trialkylboranes

Front 38

boron and hydrogen add to alkene with ___ stereochemistry

Back 38

syn

Front 39

boron (and eventually -OH) adds to the more/less highly substituted carbon

Back 39

less

Front 40

H2 with a palladium or platinum catalyst is used to

Back 40

hydrogenate alkenes

Front 41

reduction

Back 41

a reaction that results in a gain of electron density by carbon

Front 42

hydrogenation usually occurs with ___ stereochemistry

Back 42

syn

Front 43

oxidation

Back 43

a reaction that results in a loss of electron density by carbon

Front 44

peroxyacid

Back 44

RCO3H

Front 45

peroxyacids transfer . . .

Back 45

an oxygen to an alkene to make an epoxide

Front 46

epoxides can be synthesized with

Back 46

halohydrins in water and a base, like Cl2/H2O and NaOH/H2O

Front 47

glycol

Back 47

dialcohol/diol

Front 48

epoxides undergo an acid-catalyzed reaction to give a

Back 48

diol

Front 49

net result of alkene epoxidation/hydrolysis

Back 49

hydroxylation

Front 50

hydroxylation

Back 50

addition of an -OH group to each of the carbons on either side of the =

Front 51

epoxidation/hydrolysis results in cis or trans

Back 51

trans

Front 52

hydroxylation can occur without the intermediate epoxide by treating the alkene with

Back 52

osmium tetroxide, OsO4

Front 53

OsO4 results in ____

Back 53

syn addition of two -OH groups

Front 54

osmate

Back 54

intermediate in OsO4/pyridine reaction

Front 55

cyclic osmate is cleaved by using

Back 55

NaHSO3/H2O

Front 56

often used in OsO4 reactions

Back 56

NMO

Front 57

molozonide, which rearranges to form ozonide

Back 57

intermediate in ozone reaction with alkene

Front 58

ozonolysis happens with

Back 58

O3/CH2Cl2

Front 59

after ozonolysis, reduction occurs thru

Back 59

a reducing agent like Zn/CH3CO2H,H2O

Front 60

net result of ozonolysis/reduction

Back 60

two carbonyl compounds

Front 61

ketone

Back 61

R(C=O)R'

Front 62

aldehyde

Back 62

R-CHO

Front 63

phenol

Back 63

ring with C6H5 bonded to hydroxyl group

Front 64

also used for cleavage of double bonds to form carbonyl compounds

Back 64

KMnO4/H3O+

Front 65

alkenes can be cleaved following hydroxylation by

Back 65

periodic acid, HIO4, in H2O, THF

Front 66

carbene

Back 66

R2C with one lone pair

Front 67

stereospecific

Back 67

only one stereoisomer is formed as a product

Front 68

Simmons-Smith reaction

Back 68

CH2I2 + Zn(Cu) ->ICH2-ZnI

which will add the CH2 to an alkene, making cyclopropane

Front 69

carbenoid

Back 69

a metal-complexed reagent like Zn(Cu) that acts like a carbene

Front 70

3 steps of polymerization

Back 70

initiation, propagation, termination

Front 71

vinyl monomers

Back 71

substituted ethylenes

Front 72

acetylene

Back 72

the simplest alkyne

Front 73

enynes

Back 73

compounds with both double and triple bonds

Front 74

alkynes can be prepared by treatment of an dihaloalkane with

Back 74

a strong base like KOH

Front 75

HX addition to an alkyne (in excess) is usually cis/trans

Back 75

trans

Front 76

Br2 and Cl2 add to alkynes to form cis/trans alkenes

Back 76

trans

Front 77

enol

Back 77

vinylic alcohol

Front 78

tautomers

Back 78

like enol and the ketone in the hydration of an alkyne, they switch on their own

Front 79

alkynes are converted to enols and then ketones with

Back 79

H2O, H2SO4/HgSO4