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chemistry 251 > Reagents > Flashcards

Reagents Flashcards

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1
Q

Addition of X to an alkene (Markovnikov)

A

HX

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2
Q

Addition of Br to an alkene (Anti-Markovnikov)

A

HBr, ROOR

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3
Q

Addition of OH and H to an alkene (Markovnikov)

A

H3O+

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4
Q

Addition of OH and H to an alkene (Markovnikov)

A

1) Hg(OAc)2, H2O
2) NaBH4

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5
Q

Addition of OH and H to an alkene (Syn, Anti-Markovnikov)

A

1) BH3 * THF
2) H2O2, NaOH

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6
Q

Addition of 2 H to an alkene

A

H2, Pt (Pd or Ni)

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7
Q

Addition of 2 Br to an alkene (Anti)

A

Br2

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8
Q

Addition of OH and Br to an alkene (Anti, OH Markovnikov)

A

Br2, H2O

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9
Q

Addition of 2 OH to an alkene (Anti)

A

1) RCO3H
2) H3O+

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10
Q

Addition of 2 OH to an alkene (Syn)

A

KMnO4
NaOH, cold

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11
Q

Addition of 2 OH to an alkene (Syn)

A

1) OsO4
2) NaHSO3, H2O

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12
Q

Cleavage of C=C bond to form two C=O bonds

A

1) O3
2) DMS

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13
Q

Addition of H and OH to an alkene (Markovnikov)

A

Dilute H2SO4

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14
Q

Forms an alkyne from an alkane with two X groups

A

1) xs NaNH2
2) H2O

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15
Q

Addition of 2 X to an alkyne (Markovnikov)

A

xs HX

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16
Q

Addition of one X to an alkyne (Markovnikov)

A

HX (one equiv)

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17
Q

Formation of a ketone from an alkyne

A

HgSO4
H2SO4, H2O

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18
Q

Formation of an aldehyde from an alkyne

A

1) R2BH
2) H2O2, NaOH

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19
Q

Addition of two X across an alkyne

A

X2 (one equiv.)
CCl4

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20
Q

Addition of four X across an alkyne

A

xs X2
CCl4

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21
Q

Formation of a carboxylic acid from an alkyne

A

1) O3
2) H2O

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22
Q

Addition of an R group to an alkyne (Anti-Markovnikov)

A

1) NaNH2
2) RX

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23
Q

Reduction of an alkyne to an alkene (Trans)

A

Na
NH3 (l)

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24
Q

Reduction of an alkyne to an alkane (Trans R groups)

A

H2, Pt (Pd or Ni)

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25
Q

Reduction of an alkyne to an alkene (Syn)

A

H2
Lindlar’s catalyst (Ni2B)

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26
Q

Addition of Br to an alkane (Markovnikov, radical)

A

Br2
hv

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27
Q

Allylic bromination (radical)

A

NBS
hv

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28
Q

Formation of an alkoxide from an alcohol

A

NaH
or Na

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29
Q

Formation of an alcohol from an aldehyde or a ketone

A

NaBH, MeOH

30
Q

Formation of an alcohol from an aldehyde or a ketone

A

H2
Pt, Pd, or Ni

31
Q

Formation of an alcohol from an aldehyde or a ketone (always strong enough)

A

1) LiAlH4
2) H3O+

32
Q

Formation of a primary alcohol (and methanol when ester) from a carboxylic acid or ester

A

1) xs LiAlH4
2) H3O+

33
Q

Formation of an alcohol from a ketone

A

1) RMgX
2) H3O+

34
Q

Formation of an alcohol and methanol from an ester

A

1) xs RMgX
2) H3O+

35
Q

Formation of R-OTMS from R-OH

A

TMSCl
Et3N

36
Q

Formation of an alcohol from R-OTMS

A

TBAF

37
Q

Addition of X (producing H2O) to an alcohol (inversion of stereochemistry)

A

HX

38
Q

Addition of Br to an alcohol (inversion of stereochemistry)

A

1) TsCl, py
2) NaBr

39
Q

Addition of Br to an alcohol (inversion of stereochemistry)

A

PBr3

40
Q

Addition of Cl to an alcohol (inversion of stereochemistry)

A

SoCl2
py

41
Q

Addition of Cl to an alcohol

A

HCl
ZnCl2

42
Q

Reduction of an alkene (producing H2O) from an alcohol

A

conc. H2SO4
heat

43
Q

Formation of a ketone from a secondary alcohol
Formation of a carboxylic acid from a primary alcohol
Formation of a benzoquinone from a phenol

A

Na2Cr2O7
H2SO4, H2O

44
Q

Formation of an aldehyde from a primary alcohol

A

PCC, CH2Cl2

45
Q

Formation of an aldehyde from a primary alcohol

A

DMP, CH2Cl2

46
Q

Formation of an aldehyde from a primary alcohol

A

1) DMSO, (COCl2)
2) Et3N

47
Q

Formation of a ketone from a secondary alcohol

A

CrO3/H2SO4/H2O

48
Q

Formation of an ether from an alcohol

A

1) NaH
2) RX

49
Q

Formation of an alkoxy (addition of OR and H) from an alkene with one H and three R

A

1) Hg(OAc)2, ROH
2) NaBH4

50
Q

Formation of R-X + X-R + H2O from an ether
Formation of Ph-OH + R-X from an Ph-O-R

A

xs HX
heat

51
Q

Formation of a hydroperoxide from an ether

A

O2
(slow)

52
Q

Formation of an epoxide from an alkene (two R and two H)

A

MCPBA

53
Q

Formation of an epoxide from an alkene (two R and two H)

A

1) Br2, H2O
2) NaOH

54
Q

Formation of an epoxide from an alkene with an allylic OH

A

(CH3)3COOH
Ti[OCH(CH3)2]4
(+)-Det

55
Q

Formation of an epoxide from an alkene with an allylic OH

A

(CH3)3COOH
Ti[OCH(CH3)2]4
(-)-Det

56
Q

Addition of OR and OH from an epoxide (strong nucleophile)

A

1) NaOR
2) H3O+

57
Q

Addition of OH and CN from an epoxide (strong nucleophile)

A

1) NaCN
2) H3O+

58
Q

Addition of OH and RS from an epoxide (strong nucleophile)

A

1) NaSR
2) H3O+

59
Q

Addition of OH and R from an epoxide (strong nucleophile)

A

1) RMgBr
2) H3O+

60
Q

Addition of OH and H from an epoxide (strong nucleophile)

A

1) LiAlH4
2) H3O+

61
Q

Addition of OH and X to an epoxide (acid-catalyzed)

A

HX

62
Q

Addition of two OH groups to an epoxide (acid-catalyzed)

A

[H+]
H2O

63
Q

Addition of OH and OR to an epoxide (acid-catalyzed)

A

[H+]
ROH

64
Q

Formation of a thiol from an alkane with Br

A

NaSH

65
Q

Formation of a disulfide from two thiols

A

NaOH/H2O
Br2

66
Q

Formation of two thiols from a disulfide

A

HCl, Zn

67
Q

Formation of a sulfide from a thiol

A

1) NaOH
2) RX

68
Q

Addition of a methyl to a sulfide

A

MeX

69
Q

Formation of a sulfoxide from a sulfide

A

NaIO4

70
Q

Formation of a sulfone from a sulfide or a sulfoxide

A

H2O2

chemistry 251 (1 decks)

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