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lilli > o chem reagents > Flashcards

o chem reagents Flashcards

1
Q

SN1 reaction (5)

A

Multiple steps
Leaving group on tertiary Carbon
Weak nucleophile (neutral; H2O)
Protic solvent (with H)
Racemic product

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2
Q

SN2 reaction (5)

A

One step
Leaving group on primary Carbon
Strong nucleophile (charged; NaOH)
Aprotic solvent (lacking H)
Inversion

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3
Q

KOH w halide leaving group

A

Basic E2 reaction
Creates double bond toward most substituted C

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4
Q

Br2, hv

A

replaces a tertiary H with Br

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5
Q

Markovnikov’s rule

A

the rich get richer
the H atom will bond to the Carbon atom of the double bond having more H

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6
Q

acids (HBr, HCl, HI) to alkene (3)

A

Adds H and Br to C=C
Markovnikov
Racemic products

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7
Q

HBr, ROOR (peroxides), heat to alkene (2)

A

Add H and Br to C=C
Anti-markovnikov

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8
Q

H2SO4, H2O to alkene (3)

A

Adds H and OH to C=C
Markovnikov
Racemic products

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9
Q

Hg(OAc)2, H2O / NaBH4 to alkene (4)

A

Adds H and OH to C=C
Markovnikov
Anti-addition
Racemic products

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10
Q

BH3, THF / H2O2, NaOH to alkene (4)

A

Adds H and OH to C=C
Anti-markovnikov
Syn-addition
Racemic products

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11
Q

X2 (Br2, Cl2, I2) w inert solvents (CCl4) to alkene (3)

A

Adds X and X to C=C
Anti-addition
Enantiomers

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12
Q

X2 (Br2, Cl2, I2) w H2O to alkene (4)

A

Adds OH and X to C=C
OH on more substituted Carbon
Anti-addition
Enantiomers

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13
Q

H2, Pt to alkene (3)

A

Adds H and H to C=C
Syn-addition
Enantiomers

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14
Q

CH2N2 or CH2I2, heat to alkene

A

Adds CH2 to C=C forming triangle

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15
Q

mCPBA w inert solvent to alkene

A

Adds epoxide to C=C

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16
Q

mCPBA, H3O+ to alkene (3)

A

Adds OH and OH to C=C
Markovnikov
Anti-addition

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17
Q

OsO4 / H2O2 to alkene (2)

A

Adds OH and OH to C=C
Syn-addition

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18
Q

KMnO4 / NaOH to alkene C=C (2)

A

Adds OH and OH to C=C
Syn-addition

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19
Q

KMnO4 / H3O+ to alkene (2)

A

Breaks C=C
Adds =O to both Cs

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20
Q

O3 / (CH3)2S (2)

A

Breaks C=C
Adds =O to both Cs

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21
Q

NaNH2 to alkyne

A

Takes off H

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22
Q

NaNH2, R group, H3O+ to alkyne (2)

A

Takes off H
Adds R group

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23
Q

NaNH2, heat to dihalide

A

Creates alkyne

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24
Q

Na, NH3 to alkyne (2)

A

Adds H and H to triple bond (forms double bond)
Anti-addition

25
Q

1 mol Br2, CCl2 to alkene/alkyne (2)

A

Adds Br and Br
Anti-addition

26
Q

H2SO4, H2O / HgSO4 to alkyne (3)

A

Adds H and OH to alkyne
Markovnikov
Anti-addition

27
Q

HgSO4 / H3O+ to alkyne (3)

A

Adds H and OH to alkyne
Markovnikov
Anti-addition

28
Q

Sia2BH / H2O2, NaOH to alkyne (3)

A

Adds H and OH to alkyne
Anti-markovnikov
Syn-addition

29
Q

KMnO4 / H2O, neutral to alkyne

A

Adds 4 OH to alkyne

30
Q

KMnO4, KOH, H2O, heat / H3O+ to alkyne

A

Breaks alkyne and adds =O to both Cs

31
Q

O3 / H2O to alkyne

A

Breaks alkyne and adds =O and OH

32
Q

Mg, ether to RX

A

Adds Mg to halogen

33
Q

RMgX, H3O+ to =O (3)

A

Grignard reaction
R group attacks carbon with O
O becomes OH

34
Q

R2CuLi to RX (2)

A

Gilman reaction
R group kicks X and bonds

35
Q

LiAlH4 / H3O + to =O

A

Reduces =O to OH

36
Q

NaSH and XR

A

Thiol group addition to R group

37
Q

KMnO4 or NO3 to R-SH

A

R-S(=O,=O,OH)

38
Q

NaCr2O7, H2SO4 / H2O to alcohol (2)

A

Primary alcohol becomes carboxylic acid
Secondary alcohol becomes ketone

39
Q

CrO3, H2SO4 / acetone to alcohol (2),

A

Primary alcohol becomes carboxylic acid
Secondary alcohol becomes ketone

40
Q

PCC or DMP / CH2Cl2 to alcohol

A

OH becomes aldehyde or ketone

41
Q

HBr or HCl to alcohol

A

H2O forms and halide attaches to R group

42
Q

TsCl or MsCl, pyridine to alcohol

A

OH becomes OTs
OH becomes OMs

43
Q

SOCl2 / dioxane to alcohol

A

Replace OH group with Cl

44
Q

PB3 or PI3 to alcohol

A

Replace OH with Br or I

45
Q

H2SO4, heat / H2, Pt to alcohol

A

OH leaves

46
Q

TsCl, pyridine / LiAlH4 to alcohol

A

OH leaves

47
Q

H2SO4, 100 degrees C to symmetrical diols

A

One OH becomes =O and methyl group is transferred to other C
Other OH leaves

48
Q

HIO4 to gylcols (2)

A

Cleaves bonds between C connecting OH
OH become =O

49
Q

CH3CH2OTs to alkoxide

A

Adds ester chain to O-

50
Q

HBr to ether (2)

A

Breaks ether and replaces O with Br
Works with primary and secondary

51
Q

HI to ether

A

Breaks ether and places O with I
Works with tertiary

52
Q

Sulfonium salt to base

A

Sulfonium salt acts like a leaving group

53
Q

Sulfide + H2O2 + mCPBA

A

Add =O to sulfide
Add second =O to sulfide

54
Q

TiPSCl, Et3N

A

puts on protection for OH
OH becomes TiPSO

55
Q

TBAF, H2O

A

takes off protection of OH
TiPSO becomes OH

56
Q
  1. Br2 / H2O 2. NaOH / H2O
A
  1. Add Br and OH to alkene (anti)
  2. Br leaves, OH becomes epoxide
57
Q

H2SO4 / CH3OH to epoxide

A

opens epoxide ring

58
Q

CH3ONa / CH3OH to epoxide

A

opens epoxide ring

lilli (2 decks)

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