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organic chemistry 1 > unit 3 - ch 8 & 9 > Flashcards

unit 3 - ch 8 & 9 Flashcards

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1
Q

sigma (single) bonds are _____ [more/less] stable than pi (2x/3x) bonds

A

more stable

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2
Q

define an electrophilic addition reaction

A

an addition in which the electrophile bonds to one of the double-bonded carbons first, followed by the nucleophile

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3
Q

give the 2 step basic mechanism for electrophilic addition to alkenes

A
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4
Q

what element is added for a hydration addition rxn?

A

H2O

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5
Q

what element is added for a hydrogenation addition rxn?

A

H2

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6
Q

what element is added for a dihydroxylation addition rxn?

A

HOOH

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7
Q

what element is added for an oxidative cleavage addition rxn?

A

O2

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8
Q

what element is added for an epoxidation addition rxn?

A

O

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9
Q

what element is added for a halogenation addition rxn?

A

X2 (Br, Cl, I)

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10
Q

what element is added for a halohydrin formation addition rxn?

A

HOX
(X2 + H2O)

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11
Q

what element is added for an HX (hydrohalogenation) addition rxn?

A

HX

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12
Q

what element is added for a cyclopropanation addition rxn?

A

CH2

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13
Q

define markovnikov’s rule

A

when a proton acid (H atom) adds to the double bond of an alkene, it results in a product with the H atom bonded to the carbon atom that already holds the greater number of hydrogens

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14
Q

markovnikov’s rule: for an electrophilic addition to the alkene, the electrophile adds in such a way as to what?

A

to generate the most stable intermediate (carbocation)

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15
Q

for a markovnikov product to be formed, the carbocation must be on the _____ (less/more) substituted carbon. why?

A

more substituted carbon
the carbocation on the more substituted carbon allows for a more stable intermediate

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16
Q

give an example of an HX addition reaction beginning with ethene

A
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17
Q

an HX addition reaction results in what kind of product (markovnikov or anti-markovnikov)?

A

markovnikov

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18
Q

define an anti-markovnikov product

A

an orientation that is the opposite of that predicted by the original statement of markovnikov’s rule

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19
Q

anti-markovnikov orientation only works with what reagents?

A

HBr in the presence of peroxide (ROOR)

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20
Q

define the peroxide effect

A

the reversal of orientation of HBr addition to alkenes in the presence of peroxide

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21
Q

give a general 4 step (including initiation and propagation) mechanism for free radical addition of HBr to alkenes (via ROOR)

A
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22
Q

give the 2nd step & products for this free radical addition of HBr reaction

A
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23
Q

give the 3 step mechanism for acid-catalyzed hydration of an alkene

A
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24
Q

give the mechanism and products for this addition of water rxn

A
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25
Q

what is the solvent in an oxymercuration-demercuration rxn?

A

water

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26
Q

what 2 chemicals is the alkene reacted with in a hydration by oxymercuration-demercuration reaction?

A

Hg(OAc)2 (for oxymercuration) and NaBH4 (for demurcuration)

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27
Q

give a general oxymercuration-demercuration reaction beginning with ethene

A
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28
Q

give the 2 step mechanism for oxymercuration of an alkene beginning with ethene (not including demurcuration)

A
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29
Q

give the mechanism and products for this oxymercuration-demercuration rxn

A
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30
Q

what is the solvent in an alkoxymercuration-demercuration rxn?
instead of what (in oxymercuration-demercuration)?

A

alcohol instead of water

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31
Q

what 2 chemicals is the alkene reacted with in a hydration by alkoxymercuration-demercuration reaction?

A

Hg(OAc)2 (for alkoxymercuration) and NaBH4 (for demurcuration)

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32
Q

give a general alkoxymercuration-demercuration reaction beginning with ethene

A
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33
Q

give the 3 step mechanism for alkoxymercuration of an alkene (don’t need mechanism for demurcuration, but include reagent and result)

A
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34
Q

define hydroboration

A

the addition of borane or one of its derivatives to a molecule

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35
Q

BH3 is a _____ (strong/weak) electrophile and is electron _____ (rich/deficient)

A

strong, deficient

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36
Q

hydroboration-oxidation is a stereospecific reaction, so it reacts in a ____ (syn/anti) addition manner so that the additives are on the _____ (same/different)

A

syn addition, same

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37
Q

give a general hydroboration-oxidation reaction beginning with ethene

A
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38
Q

hydroboration-oxidation: boron adds to the ____ (more/less) hindered & substituted carbon and hydrogen adds to the _____ (more/less) substituted carbon, which is _____ (markovnikov/anti-markovnikov)

A

less, more, anti-markovnikov

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39
Q

define an inert solvent

A

a solvent with organic compounds

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40
Q

what are 3 examples of good inert solvents that can be used in addition of halogen to alkene rections?

A

CCl4, CHCl3, and CH2CL2

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41
Q

addition of halogen to alkene rxns produce _____ (syn/anti) addition products

A

anti-addition

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42
Q

give a general addition of halogens to alkenes rxn beginning with ethene

A
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43
Q

give the 2 step mechanism for adding halogens to alkenes beginning with ethene

A
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44
Q

addition of halogens to alkenes products will be added in the _____ (cis/trans) formation and not the _____ (cis/trans) formation
why?

A

yes trans, no cis
cis structure won’t form because of sterics

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45
Q

define a halohydrin

A

an alcohol with a halogen on the adjacent carbon

46
Q

halohydrin rxns must have a good nucleophile present, like which 2 solvents?

A

water or an OR group

47
Q

halohydrin addition rxn from a _____ (syn/anti) addition and _____ (markovnikov/anti-markovnikov) product

A

anti addition
markovnikov product

48
Q

give a general halohydrin addition rxn beginning with cyclopentene

A
49
Q

give the 2 step mechanism for a halohydrin addition rxn beginning with ethene

A
50
Q

what are the non organic reactants in a halohydrin addition rxn?

A

X2 (halogen)
H20

51
Q

catalytic hydrogenation of alkenes results in _____ (syn/anti) addition

A

syn addition

52
Q

what are the 2 nonorganic reactants involved in a catalytic hydrogenation of alkenes reaction?

A

H2
catalyst: solids Pt, Pd, or Ni

53
Q

give a general catalytic hydrogenation of alkenes reaction beginning with ethene

A
54
Q

an addition of carbenes to alkenes reaction uses what organic solvent reactant to produce methylene?

A

CH2N2 (results in a carbon with 2 open valence electrons)

55
Q

give a general reaction of addition of carbenes to alkenes beginning with ethene

A
56
Q

what is the simmons-smith reactant?

A

I-CH2-Zn-I

57
Q

which 3 reactants together produce the simmons-smith reactant?

A

CH2I2, Zn, Cu

58
Q

give a simmons smith reactions beginning with ethene

A
59
Q

give a simmons smith reaction beginning with cyclohexene

A
60
Q

which 3 reactants are involved in a formation of carbenes by alpha elimination rxn?

A

CHX3 (halogen), NaOH, H2O

61
Q

give an example of a formation of carbenes by alpha elimination rxn beginning with the following reactant + CHBr3

A
62
Q

give a general epoxidation of alkenes rxn beginning with the following reactants

A
63
Q

which 2 reactants beside the major reactant are involved in an epoxidation of alkenes rxn?

A

MCPBA or MMPP
CH2Cl2

64
Q

give the 3 step mechanism for acid-catalyzed opening of epoxides

A
65
Q

define hydroxylation

A

the addition of two hydroxl groups - one at each carbon of the double bond

66
Q

what are the 2 possible combinations of reagents besides the major reactant used in a hydroxylation rxn?

A

OsO4 and H2O2 or
KMnO4 and -OH

67
Q

give a hydroxylation rxn beginning with ethene & using OsO4 + H2O2

A
68
Q

give the mechanism for an osmium tetroxide dihydroxylation (hydroxylation) rxn beginning with cyclopentene

A
69
Q

give the mechanism for a permanganate dihydroxylation (hydroxylation) rxn beginning with cyclopentene

A
70
Q

what is the nonorganic reactant (& its properties) that results in oxidative cleavage of alkenes?

A

warm, concentrated KMnO4

71
Q

give an oxidative cleavage of alkenes reaction beginning with the following reactant

A
72
Q

give the products of an oxidative cleavage reaction beginning with the following reactant

A
73
Q

what are the 2 non major reactant used in an ozonolysis reaction?

A

O3 and (CH3)2S

74
Q

give an ozonolysis reaction beginning with the following reactant

A
75
Q

define an alkyne

A

a hydrocarbon containing a carbon-carbon triple bond

76
Q

what is the strength of a C-C triple bond in kJ/mol?

A

837 kJ/mol

77
Q

how many degrees of unsaturation does a typical alkyne have?

A

2

78
Q

T or F: when naming alkenes and alkynes, alcohol groups have a higher numbering priority

A

true

79
Q

define a terminal alkyne

A

an organic compound that has a triple bond at the end of the chain

80
Q

define an internal alkyne

A

an organic compound that has a triple bond somewhere other than at the end of a chain

81
Q

define an acetylenic hydrogen - is it acidic?

A

a hydrogen bonded to the end carbon of a terminal alkyne
mildly acidic

82
Q

what is the structure of acetylene?

A
83
Q

are alkynes more or less acidic than alkenes and alkanes?

A

more acidic

84
Q

give the products for the following alkyne reaction

A

no rxn because there is no acidic/terminal proton

85
Q

acetylide is a _____ (strong/weak) base and a _____ (powerful/weak) nucleophile

A

strong, powerful

86
Q

alkylation of acetylide ions works in a(n) _____ (Sn1/Sn2/E1/E2) fashion

A

Sn2

87
Q

what is the non major reactant in an alkylation of acetylide ions reaction?

A

R-X (X = primary alkyl halide)

88
Q

give the mechanism and products of an alkylation of acetylide ions reaction using the following reactants

A
89
Q

give the products of an alkylation of acetylide ions reaction using the following reactants

A
90
Q

what are the 2 non major reactants used in an addition of acetylide ions to carbonyl group reaction?

A

an aldehyde or ketone
H3O+

91
Q

give the mechanism and products of an addition of acetylide ions to carbonyl group reaction using the following reactants

A
92
Q

in a synthesis of alkynes by elimination reaction, the first step is _____ (fast/slow) and the second step is very _____ (fast/slow) and requires a _____ (higher/lower) temperature

A

fast, slow, higher temp

93
Q

in a synthesis of alkynes by elimination reaction, using KOH as a reactant will form a stable _____ (internal/terminal) alkyne

A

stable internal alkyne

94
Q

in a synthesis of alkynes by elimination reaction, using NaNH2 as a reactant will form a _____ (internal/terminal) alkyne

A

terminal

95
Q

give an example of a vicinal dihalide using ethane

A
96
Q

give an example of a geminal dihalide using ethane

A
97
Q

give an example of a synthesis of alkynes by elimination reaction using the following reactants

A
98
Q

give a catalytic hydrogenation to alkanes reaction using the following reactant

A
99
Q

what is the necessary reagent to use in a catalytic hydrogenation to a cis alkene reaction when you want to stop at the alkene and not go all the way to the alkane?

A

Lindlar’s catalyst

100
Q

give a catalytic hydrogenation to cis alkenes reaction using the following reactant

A
101
Q

what is the reagent to use in a metal-ammonia reduction to a trans alkene reaction?

A

Na/NH3

102
Q

give a metal-ammonia reduction to trans alkene reaction using the following reactant

A
103
Q

give the 4 step mechanism for a metal-ammonia reduction of an alkyne reaction

A
104
Q

give an addition of halogens –> alkene reaction using the following reactants

A
105
Q

what reagent is used in an addition of halogens –> alkene reaction?

A

X2 (Cl2 or Br2)

106
Q

what reagent is used in an addition of halogens –> alkane reaction?

A

excess (2) X2

107
Q

give an addition of halogens –> alkane reaction using the following reactants

A
108
Q

what reagent is used in an addition of hydrogen halide reaction?

A

H-X

109
Q

give the reaction mechanism of an addition of hydrogen halide reaction using ethyne and one equivalent of H-X

A
110
Q

an addition of hydrogen halide reaction –> alkene reaction results in a(n) _______ (ant-markov/markovnikov) product

A

markovnikov

111
Q

give the major products of an addition of hydrogen halide reaction using the following reactants

A

organic chemistry 1 (2 decks)

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