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Mechanisms Flashcards

1
Q

What is required to go from an alkene to a vicinal diols?

A

1) OsO4

2) NaHSO3

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2
Q

What is the product of a reaction with an alkyne and 2X2?

A

vicinal tetrahalide

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3
Q

What is the product of a reaction with an alkene and HX?

A

haloalkane
Regiochemistry: Markovnikov
Stereochemistry: mixed

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4
Q

What is the product of a reaction with an alkyne and HgSO4, H2SO4, H2O?

A

ketone

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5
Q

What is the product of a reaction with an alkene and X2, H2O?

A

halohydrin
Regiochemistry: OH on more substituted carbon
Stereochemistry: anti

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6
Q

What is required to go from an alkene to a haloalkane?

A

HX

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7
Q

What is the product of a reaction with an alkene and X2?

A

vicinal dihalide

Stereochemistry: anti

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8
Q

What is the product of a reaction with an alkyne and H2 and Lindlar’s Catalyst?

A

alkene

Regiochemistry: Z product (syn)

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9
Q

What is required to go from an alkyne to a aldehyde?

A

1) (sia)2BH

2) NaOH/H2O2

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10
Q

What is the product of a reaction with an alkyne and Na/NH3?

A

alkene

Regiochemistry: E product (anti)

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11
Q

What is the product of a reaction with an alkene and 1) OsO4

2) NaHSO3?

A

vicinal diol

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12
Q

What is required to go from an alkene to a syn, non-MArkovnikov alcohol?

A

1) BH3

2) H2O2/OH-

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13
Q

What is the product of a reaction with an alkene and H2, Pd, Pt, Ni?

A

alkane

Stereochemistry: syn

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14
Q

What is the product of a reaction with an alkyne and 2HX?

A

germinal dihalide

Regiochemistry: Markovnikov with terminal alkynes

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15
Q

What is the product of a reaction with an alkyne and 1) NaNH2
2) RCH2X?

A

an alkyne (made a C-C bond)

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16
Q

What is required to go from an alkene to an alkane?

A

H2, Pd, Pt, Ni

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17
Q

What is the product of a reaction with a vicinal dihalide and 1) 3 NaNH2
2) H2O/HCl?

A

terminal alkyne

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18
Q

What is the product of a reaction with an alkene and 1) Hg(OAc)2/H2O
2) NaBH4?

A

alcohol
Regiochemistry: Markovnikov, no rearrangement
Stereochemistry: mixed

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19
Q

What is the product of a reaction with an alkyne and 1) (sia)2BH
2) NaOH/H2O2?

A

aldehyde

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20
Q

What is required to go from an alkyne to a ketone?

A

HgSO4, H2SO4, H2O

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21
Q

What is the product of a reaction with an alkane and Br2, hv?

A

haloalkane

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22
Q

What is required to go from a vicinal dihalide to an alkyne?

A

2 NaNH2 for an internal alkyne or
1) 3 NaNH2
2) H2O/HCl
for a terminal alkyne

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23
Q

What is required to go from an alkane to a haloalkane?

A

Br2, hv

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24
Q

What is required to go from an alkene to a mixed, Markovnikov alcohol?

A

H2O,H2SO4 (cat)

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25
What is required to go from an alkene to a mixed, no rearranged non Markovnikov alcohol?
1) Hg(OAc)2/H2O | 2) NaBH4
26
What is the product of a reaction with an alkene and 1) O3 | 2) (CH3)2S?
ketone, C=C bond breaks
27
What is required to go from an alkene to a ketone?
1) O3 2) (CH3)2S carbon=carbon bond breaks
28
What is required to go from an alkyne to a vicinal tetrahalide?
2X2
29
What is the product of a reaction with a vicinal dihalide and 2 NaNH2?
internal alkyne
30
What is required to go from an alkene to a halohydrin?
X2, H2O
31
What is required to go from an alkene to a vicinal dihalide?
X2
32
What is the product of a reaction with an alkene and H2O,H2SO4 (cat)?
alcohol Regiochemistry: Markovnikov Stereochemistry: mixed
33
What is required to go from an alkyne to an alkyne?
1) NaNH2 2) RCH2X makes a C-C bond
34
What is the product of a reaction with an alkene and 1) BH3 | 2) H2O2/OH-?
alcohol Regiochemistry: non-Markovnikov Stereochemistry: syn
35
What is required to go from an alkyne to an alkene?
Na/NH3 for an E product or H2 and Lindlar's Catalyst for a Z product
36
What is required to go from an alkyne to an alkane?
2H2 and Pd, PT, Ni
37
What is the product of a reaction with an alkyne and 2H2 and Pd, PT, Ni?
alkane
38
What is required to from an alkyne to a germinal dihalide?
2HX
39
What is required to go from an alkene to a haloalkene?
NBS
40
What is the product formed when an alkene reacts with NBS?
haloalkene; most stable alkene product
41
What is required to go from an alkene to an epoxide?
RCO3H
42
What is the product formed when an alkene reacts with RCO3H?
epoxide | Stereochemistry: syn
43
What is required to go from primary haloalkane to an alkene?
tBuOK
44
What is required to go from a secondary/tertiary haloalkane to an alkene?
RO-/ strong base by E2 Regiochemistry: Zaitsev Stereochemistry: Anti periplanar
45
What is the product formed when a primary haloalkane reacts with tBuOK?
alkene Regiochemistry: Zaitsev Stereochemistry: Anti periplanar
46
What is the product formed when a secondary/tertiary alkane reacts with RO-/strong base?
alkene Regiochemistry: Zaitsev Stereochemistry: Anti periplanar
47
What is required to go from an epoxide to a Markovnikov vicinal diol?
H3O+
48
What is required to go from an epoxide to a non-Markovnikov vicinal diol?
HO-
49
What is the product form when an epoxide reacts with H3O+?
vincinal diol Regiochemistry: Markovnikov Stereochemistry: anti
50
What is the product form when an epoxide reacts with HO-?
vincinal diol Regiochemistry: non-Markovnikov Stereochemistry: anti
51
What is required to go from a halohydrin to an epoxide?
RO- by Sn2
52
What is the product formed wen a halohydrin reacts with RO-?
epoxide | Stereochemistry: anti-periplanar
53
What is required to go from a primary haloalkane to an ether?
RO- by Sn2
54
What is the product formed when a primary haloalkane reacts with RO-?
ether
55
What is required to go from a secondary/tertiary alcohol to an alkene?
H2SO4 by E1
56
What is the product formed when a secondary/tertiary alcohol reacts with H2SO4?
alkene | Regiochemistry: Zaitsev
57
What is required to go from a tertiary alcohol to a haloalkane?
ROH or HX by Sn1
58
What is the product formed when a tertiary alcohol reacts with ROH or HX?
haloalkane | Stereochemisry: scrambled
59
What is required to go from a primary/secondary alcohol to a haloalkane?
PBr3 or SOCl2 by Sn2
60
What is the product formed when a primary or secondary alcohol reacts with PBr3 or SOCl2?
haloalkane | Stereochemstry: inversion
61
What is required to go from a primary/secondary alcohol to a sulfonate ester?
2 RSO2Cl
62
What is the product formed when a primary or secondary alcohol reacts with 2 RSO2Cl?
sulfonate ester
63
What is required to go from a primary alcohol to a carboxylic acid?
H2CrO4
64
What is the product formed when an alcohol reacts with H2CrO4?
carboxylic acid
65
What is required to go from a primary alcohol to an aldehyde?
PCC
66
What is the product formed when a primary alcohol reacts with PCC?
aldehyde
67
What is required to go from a secondary alcohol to ketone?
H2CrO4
68
What is the product formed when a secondary alcohol reacts with H2CrO4?
ketone

Organic Chemistry (69 decks)

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