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Organic Chemistry > Mechanisms > Flashcards

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
Q

What is required to go from an alkene to a mixed, no rearranged non Markovnikov alcohol?

A

1) Hg(OAc)2/H2O

2) NaBH4

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26
Q

What is the product of a reaction with an alkene and 1) O3

2) (CH3)2S?

A

ketone, C=C bond breaks

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27
Q

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

A

1) O3
2) (CH3)2S
carbon=carbon bond breaks

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28
Q

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

A

2X2

29
Q

What is the product of a reaction with a vicinal dihalide and 2 NaNH2?

A

internal alkyne

30
Q

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

A

X2, H2O

31
Q

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

A

X2

32
Q

What is the product of a reaction with an alkene and H2O,H2SO4 (cat)?

A

alcohol
Regiochemistry: Markovnikov
Stereochemistry: mixed

33
Q

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

A

1) NaNH2
2) RCH2X
makes a C-C bond

34
Q

What is the product of a reaction with an alkene and 1) BH3

2) H2O2/OH-?

A

alcohol
Regiochemistry: non-Markovnikov
Stereochemistry: syn

35
Q

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

A

Na/NH3 for an E product
or
H2 and Lindlar’s Catalyst for a Z product

36
Q

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

A

2H2 and Pd, PT, Ni

37
Q

What is the product of a reaction with an alkyne and 2H2 and Pd, PT, Ni?

A

alkane

38
Q

What is required to from an alkyne to a germinal dihalide?

A

2HX

39
Q

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

A

NBS

40
Q

What is the product formed when an alkene reacts with NBS?

A

haloalkene; most stable alkene product

41
Q

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

A

RCO3H

42
Q

What is the product formed when an alkene reacts with RCO3H?

A

epoxide

Stereochemistry: syn

43
Q

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

A

tBuOK

44
Q

What is required to go from a secondary/tertiary haloalkane to an alkene?

A

RO-/ strong base by E2
Regiochemistry: Zaitsev
Stereochemistry: Anti periplanar

45
Q

What is the product formed when a primary haloalkane reacts with tBuOK?

A

alkene
Regiochemistry: Zaitsev
Stereochemistry: Anti periplanar

46
Q

What is the product formed when a secondary/tertiary alkane reacts with RO-/strong base?

A

alkene
Regiochemistry: Zaitsev
Stereochemistry: Anti periplanar

47
Q

What is required to go from an epoxide to a Markovnikov vicinal diol?

A

H3O+

48
Q

What is required to go from an epoxide to a non-Markovnikov vicinal diol?

A

HO-

49
Q

What is the product form when an epoxide reacts with H3O+?

A

vincinal diol
Regiochemistry: Markovnikov
Stereochemistry: anti

50
Q

What is the product form when an epoxide reacts with HO-?

A

vincinal diol
Regiochemistry: non-Markovnikov
Stereochemistry: anti

51
Q

What is required to go from a halohydrin to an epoxide?

A

RO- by Sn2

52
Q

What is the product formed wen a halohydrin reacts with RO-?

A

epoxide

Stereochemistry: anti-periplanar

53
Q

What is required to go from a primary haloalkane to an ether?

A

RO- by Sn2

54
Q

What is the product formed when a primary haloalkane reacts with RO-?

A

ether

55
Q

What is required to go from a secondary/tertiary alcohol to an alkene?

A

H2SO4 by E1

56
Q

What is the product formed when a secondary/tertiary alcohol reacts with H2SO4?

A

alkene

Regiochemistry: Zaitsev

57
Q

What is required to go from a tertiary alcohol to a haloalkane?

A

ROH or HX by Sn1

58
Q

What is the product formed when a tertiary alcohol reacts with ROH or HX?

A

haloalkane

Stereochemisry: scrambled

59
Q

What is required to go from a primary/secondary alcohol to a haloalkane?

A

PBr3 or SOCl2 by Sn2

60
Q

What is the product formed when a primary or secondary alcohol reacts with PBr3 or SOCl2?

A

haloalkane

Stereochemstry: inversion

61
Q

What is required to go from a primary/secondary alcohol to a sulfonate ester?

A

2 RSO2Cl

62
Q

What is the product formed when a primary or secondary alcohol reacts with 2 RSO2Cl?

A

sulfonate ester

63
Q

What is required to go from a primary alcohol to a carboxylic acid?

A

H2CrO4

64
Q

What is the product formed when an alcohol reacts with H2CrO4?

A

carboxylic acid

65
Q

What is required to go from a primary alcohol to an aldehyde?

A

PCC

66
Q

What is the product formed when a primary alcohol reacts with PCC?

A

aldehyde

67
Q

What is required to go from a secondary alcohol to ketone?

A

H2CrO4

68
Q

What is the product formed when a secondary alcohol reacts with H2CrO4?

A

ketone

Organic Chemistry (69 decks)

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