Brainscape's Knowledge GenomeTM


Top Flashcards (Certified)
All Flashcards

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

unit 3 - ch 8 & 9 Flashcards

(111 cards)

Start Studying
1
Q

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

A

more stable

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
3
Q

give the 2 step basic mechanism for electrophilic addition to alkenes

A
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
4
Q

what element is added for a hydration addition rxn?

A

H2O

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
5
Q

what element is added for a hydrogenation addition rxn?

A

H2

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
6
Q

what element is added for a dihydroxylation addition rxn?

A

HOOH

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
7
Q

what element is added for an oxidative cleavage addition rxn?

A

O2

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
8
Q

what element is added for an epoxidation addition rxn?

A

O

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
9
Q

what element is added for a halogenation addition rxn?

A

X2 (Br, Cl, I)

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
10
Q

what element is added for a halohydrin formation addition rxn?

A

HOX
(X2 + H2O)

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
11
Q

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

A

HX

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
12
Q

what element is added for a cyclopropanation addition rxn?

A

CH2

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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)

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
16
Q

give an example of an HX addition reaction beginning with ethene

A
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
17
Q

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

A

markovnikov

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
19
Q

anti-markovnikov orientation only works with what reagents?

A

HBr in the presence of peroxide (ROOR)

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
20
Q

define the peroxide effect

A

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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
21
Q

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

A
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
22
Q

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

A
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
23
Q

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

A
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
24
Q

give the mechanism and products for this addition of water rxn

A
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
25
what is the solvent in an oxymercuration-demercuration rxn?
water
26
what 2 chemicals is the alkene reacted with in a hydration by oxymercuration-demercuration reaction?
Hg(OAc)2 (for oxymercuration) and NaBH4 (for demurcuration)
27
give a general oxymercuration-demercuration reaction beginning with ethene
28
give the 2 step mechanism for oxymercuration of an alkene beginning with ethene (not including demurcuration)
29
give the mechanism and products for this oxymercuration-demercuration rxn
30
what is the solvent in an alkoxymercuration-demercuration rxn? instead of what (in oxymercuration-demercuration)?
alcohol instead of water
31
what 2 chemicals is the alkene reacted with in a hydration by alkoxymercuration-demercuration reaction?
Hg(OAc)2 (for alkoxymercuration) and NaBH4 (for demurcuration)
32
give a general alkoxymercuration-demercuration reaction beginning with ethene
33
give the 3 step mechanism for alkoxymercuration of an alkene (don't need mechanism for demurcuration, but include reagent and result)
34
define hydroboration
the addition of borane or one of its derivatives to a molecule
35
BH3 is a _____ (strong/weak) electrophile and is electron _____ (rich/deficient)
strong, deficient
36
hydroboration-oxidation is a stereospecific reaction, so it reacts in a ____ (syn/anti) addition manner so that the additives are on the _____ (same/different)
syn addition, same
37
give a general hydroboration-oxidation reaction beginning with ethene
38
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)
less, more, anti-markovnikov
39
define an inert solvent
a solvent with organic compounds
40
what are 3 examples of good inert solvents that can be used in addition of halogen to alkene rections?
CCl4, CHCl3, and CH2CL2
41
addition of halogen to alkene rxns produce _____ (syn/anti) addition products
anti-addition
42
give a general addition of halogens to alkenes rxn beginning with ethene
43
give the 2 step mechanism for adding halogens to alkenes beginning with ethene
44
addition of halogens to alkenes products will be added in the _____ (cis/trans) formation and not the _____ (cis/trans) formation why?
yes trans, no cis cis structure won't form because of sterics
45
define a halohydrin
an alcohol with a halogen on the adjacent carbon
46
halohydrin rxns must have a good nucleophile present, like which 2 solvents?
water or an OR group
47
halohydrin addition rxn from a _____ (syn/anti) addition and _____ (markovnikov/anti-markovnikov) product
anti addition markovnikov product
48
give a general halohydrin addition rxn beginning with cyclopentene
49
give the 2 step mechanism for a halohydrin addition rxn beginning with ethene
50
what are the non organic reactants in a halohydrin addition rxn?
X2 (halogen) H20
51
catalytic hydrogenation of alkenes results in _____ (syn/anti) addition
syn addition
52
what are the 2 nonorganic reactants involved in a catalytic hydrogenation of alkenes reaction?
H2 catalyst: solids Pt, Pd, or Ni
53
give a general catalytic hydrogenation of alkenes reaction beginning with ethene
54
an addition of carbenes to alkenes reaction uses what organic solvent reactant to produce methylene?
CH2N2 (results in a carbon with 2 open valence electrons)
55
give a general reaction of addition of carbenes to alkenes beginning with ethene
56
what is the simmons-smith reactant?
I-CH2-Zn-I
57
which 3 reactants together produce the simmons-smith reactant?
CH2I2, Zn, Cu
58
give a simmons smith reactions beginning with ethene
59
give a simmons smith reaction beginning with cyclohexene
60
which 3 reactants are involved in a formation of carbenes by alpha elimination rxn?
CHX3 (halogen), NaOH, H2O
61
give an example of a formation of carbenes by alpha elimination rxn beginning with the following reactant + CHBr3
62
give a general epoxidation of alkenes rxn beginning with the following reactants
63
which 2 reactants beside the major reactant are involved in an epoxidation of alkenes rxn?
MCPBA or MMPP CH2Cl2
64
give the 3 step mechanism for acid-catalyzed opening of epoxides
65
define hydroxylation
the addition of two hydroxl groups - one at each carbon of the double bond
66
what are the 2 possible combinations of reagents besides the major reactant used in a hydroxylation rxn?
OsO4 and H2O2 or KMnO4 and -OH
67
give a hydroxylation rxn beginning with ethene & using OsO4 + H2O2
68
give the mechanism for an osmium tetroxide dihydroxylation (hydroxylation) rxn beginning with cyclopentene
69
give the mechanism for a permanganate dihydroxylation (hydroxylation) rxn beginning with cyclopentene
70
what is the nonorganic reactant (& its properties) that results in oxidative cleavage of alkenes?
warm, concentrated KMnO4
71
give an oxidative cleavage of alkenes reaction beginning with the following reactant
72
give the products of an oxidative cleavage reaction beginning with the following reactant
73
what are the 2 non major reactant used in an ozonolysis reaction?
O3 and (CH3)2S
74
give an ozonolysis reaction beginning with the following reactant
75
define an alkyne
a hydrocarbon containing a carbon-carbon triple bond
76
what is the strength of a C-C triple bond in kJ/mol?
837 kJ/mol
77
how many degrees of unsaturation does a typical alkyne have?
2
78
T or F: when naming alkenes and alkynes, alcohol groups have a higher numbering priority
true
79
define a terminal alkyne
an organic compound that has a triple bond at the end of the chain
80
define an internal alkyne
an organic compound that has a triple bond somewhere other than at the end of a chain
81
define an acetylenic hydrogen - is it acidic?
a hydrogen bonded to the end carbon of a terminal alkyne mildly acidic
82
what is the structure of acetylene?
83
are alkynes more or less acidic than alkenes and alkanes?
more acidic
84
give the products for the following alkyne reaction
no rxn because there is no acidic/terminal proton
85
acetylide is a _____ (strong/weak) base and a _____ (powerful/weak) nucleophile
strong, powerful
86
alkylation of acetylide ions works in a(n) _____ (Sn1/Sn2/E1/E2) fashion
Sn2
87
what is the non major reactant in an alkylation of acetylide ions reaction?
R-X (X = primary alkyl halide)
88
give the mechanism and products of an alkylation of acetylide ions reaction using the following reactants
89
give the products of an alkylation of acetylide ions reaction using the following reactants
90
what are the 2 non major reactants used in an addition of acetylide ions to carbonyl group reaction?
an aldehyde or ketone H3O+
91
give the mechanism and products of an addition of acetylide ions to carbonyl group reaction using the following reactants
92
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
fast, slow, higher temp
93
in a synthesis of alkynes by elimination reaction, using KOH as a reactant will form a stable _____ (internal/terminal) alkyne
stable internal alkyne
94
in a synthesis of alkynes by elimination reaction, using NaNH2 as a reactant will form a _____ (internal/terminal) alkyne
terminal
95
give an example of a vicinal dihalide using ethane
96
give an example of a geminal dihalide using ethane
97
give an example of a synthesis of alkynes by elimination reaction using the following reactants
98
give a catalytic hydrogenation to alkanes reaction using the following reactant
99
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?
Lindlar's catalyst
100
give a catalytic hydrogenation to cis alkenes reaction using the following reactant
101
what is the reagent to use in a metal-ammonia reduction to a trans alkene reaction?
Na/NH3
102
give a metal-ammonia reduction to trans alkene reaction using the following reactant
103
give the 4 step mechanism for a metal-ammonia reduction of an alkyne reaction
104
give an addition of halogens --> alkene reaction using the following reactants
105
what reagent is used in an addition of halogens --> alkene reaction?
X2 (Cl2 or Br2)
106
what reagent is used in an addition of halogens --> alkane reaction?
excess (2) X2
107
give an addition of halogens --> alkane reaction using the following reactants
108
what reagent is used in an addition of hydrogen halide reaction?
H-X
109
give the reaction mechanism of an addition of hydrogen halide reaction using ethyne and one equivalent of H-X
110
an addition of hydrogen halide reaction --> alkene reaction results in a(n) _______ (ant-markov/markovnikov) product
markovnikov
111
give the major products of an addition of hydrogen halide reaction using the following reactants

organic chemistry 1 (2 decks)

Brainscape helps you reach your goals faster, through stronger study habits.
© 2025 Bold Learning Solutions. Terms and Conditions