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CHEM 246 > EXAM 2 > Flashcards

EXAM 2 Flashcards

1
Q

to produce diol what reactants should you use

A

OsO4 and NaHSO3

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2
Q

what does OsO4 do

A

breaks double bond and adds oxygens of OsO4 to same side

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3
Q

what does NaHSO3 do

A

makes same sided oxygens into same sided alcohols

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4
Q

what do [H] and H3O+ do?

A

breaks double bonded oxygen, adds H to O to yield alcohol, adds another H

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5
Q

what reactants should you use to partially reduce carboxylic acid?

A

NaBH4 and EtOH

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6
Q

what reactants should you use to fully reduce carboxylic acid?

A

LiAlH4 and Et2O

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7
Q

what reactant should you use to reduce carboxylic acid and add R group?

A

RMgX

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8
Q

what reactants does not react with ester?

A

NaBH4

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9
Q

what reactants should you use to reduce ester?

A

Et2O and LiAlH4

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10
Q

what reactants should you use to make alcohol out of aldehydes and ketones?

A

LiAlH4, NaBH4, RMgX

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11
Q

what does LiAlH4 and H3O+ do?

A

breaks double bond of carboxylic acid and adds H

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12
Q

what are common Rs?

A

alkyl, aryl, methyl alkene (no idea what it actually is)

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13
Q

what is different about a Grignard reactant?

A

it still reduces but adds an R group instead of an H

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14
Q

what does CH3MgBr and H3O+ do to reactant containing alcohol?

A

takes H from OH leaving O- on carbon chain with other products of CH4 and MgBr+

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15
Q

what does CH3MgBr and H3O+ do to

A

breaks double bonded oxygen to yield OH, breaks off other oxygen, adds 2 methyls (see pic) and another reactant of CH3OH (reacts twice!!)

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16
Q

what reactant should you use to replace tertiary alcohol?

A

HCl/HBr

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17
Q

what reactant should you use to replace primary/secondary alcohol?

A

SOCl2/PBr3

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18
Q

what reactants should you use for oxidation?

A

CrO3 or Dess Martin pyridine

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19
Q

what reactant should you use to oxidize to carboxylic acid?

A

CrO3

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20
Q

what reactant should you use to oxidize to aldehyde?

A

dess martin

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21
Q

what yields from oxidizing a primary alcohol?

A

yields either carboxylic acid or aldehyde

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22
Q

what yields from oxidizing a tertiary alcohol?

A

no reaction

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23
Q

what is stronger between CrO3 and Dess Martin?

A

CrO3

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24
Q

what happens when you react CrO3 with a primary alcohol?

A

2 step process that yields carboxylic acid

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25
Q

what happens when you reacts CrO3 with secondary alcohol?

A

removes both Hs, turns single bond O to double bond

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26
Q

what happens when you react dess Martin and pyridine with primary alcohol?

A

yields aldehyde

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27
Q

what happens when you react dess Martin and pyridine with secondary alcohol

A

removes both Hs, turns single bond O to double bond

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28
Q

what reactants do you use for WilliamSon ether synthesis?

A

NaH and THF

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29
Q

what is the simplified rxn for WilliamSon ether synthesis?

A

ROH + R’X —> R-O-R’ + HX

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30
Q

in WilliamSon ether synthesis, which reactant is most hindered?

A

ROH (3º>2º>1º)

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31
Q

in WilliamSon ether synthesis, which reactant is least hindered?

A

RX

32
Q

what reactant do you use for acidic cleavage?

A

HX

33
Q

what is the simplified rxn for acidic cleavage?

A

R-O-R’ –> ROH + R’X

34
Q

what reactant should you use for reverse of acidic cleavage?

A

NaH

35
Q

what are the most hindered in acidic cleavage?

A

ROH primary and secondary

36
Q

what are the least hindered in acidic cleavage?

A

tertiary ROH

37
Q

what reactant should you use to make an epoxide?

A

mCPBA

38
Q

describe primary alcohol

A

carbon w/ OH, 2 H, 1 R

39
Q

describe tertiary alcohol

A

carbon w/ OH, 3 R

39
Q

describe secondary alcohol

A

carbon w/ OH, H, 2 R

40
Q

how to name alcohol and phenols

A

number longest carbon chain by OH group, # substituents in ABC order, replace -e w -ol

41
Q

a less hindered O atom is more/less stable?

A

more

42
Q

more inductive effect more/less acidic?

A

more so more stable

43
Q

what are weak acids that do not react with weak bases (like amines) and have limited rxns with things like NaOH?

A

alcohols

44
Q

what is more acidic, phenol or alcohol?

A

PHENOL!

45
Q

are phenols with electron withdrawing more/less acidic than phenol itself?

A

more

46
Q

are phenols with electron donating more/less acidic than phenol itself?

A

less

47
Q

What reactants do you need to go from RSH to R-S-R’?

A

NaH and R’X

48
Q

What does NaH yield from RSH?

A

RS-

49
Q

What does R’X yield from RS-?

A

R-S-R’

50
Q

what reactants should you use for alkoxylmercuration rxn?

A

ROH, Hg(AC)2 and NaBH4

51
Q

what happens when you react ROH, Hg(AC)2, and NaBH4 with an alkene?

A

breaks double bond, adds OR to most hindered and H to least hindered

52
Q

what does mCPBA do?

A

breaks double bond, creates epoxide

53
Q

what does NaOCH3 and H2O do to epoxide?

A

breaks epoxide and adds OH at primary, methyl on other side of O

54
Q

what does HBr do to an epoxide?

A

breaks epoxide and adds OH at more hindered, removes O, Br at end of other C chain

55
Q

what does HBr do to an epoxide w double bond on ring?

A

breaks epoxide and adds Br at more hindered, removes O, OH at end of other C chain

56
Q

what does RBr do to episulfide?

A

breaks episulfide and adds Br at less hindered, methyl on other side of S

57
Q

What does NaH?

A

takes away LG from one reactant, H from the other, and synthesizes the reactants

58
Q

list ketone, carboxylic acid, and aldehyde in order of increasing strength and discuss reaction rate comparatively

A

ketone < aldehyde < carboxylic acid

ketone fastest and weakest

59
Q

What happens when Li oxidizes?

A

it is stronger so it cleaves and any O goes to OH

60
Q

Grignard reactants do what?

A

add R (can be Cs) and OH

61
Q

what happens when you use 2 equivalent Grignard reactants?

A

it removes the OR group first (goes through two rxns)

62
Q

what are things that help prove more acidity?

A

lower pKa, more stable, more inductive, more EN

63
Q

what does an acid and heat do?

A

removes OH and makes double bond on markovnikov

64
Q

what will HBr do?

A

cleaves bond, forms OH on more hindered, Br on less hindered

65
Q

what does CH3Br do to episulfide?

A

S to CH3 on more hindered, Br on less hindered

66
Q

what kind of rxn uses NaH

A

WilliamSon

67
Q

what does SOCl2 do?

A

replaces OH with Cl

68
Q

what does PBr3 do?

A

replaces OH with Br

69
Q

what do Na, BH4 do?

A

go to anti-markov

70
Q

what do you need for Grignard rxn

A

C=O

71
Q

what does ROH (Hg) do?

A

breaks double bond, adds ether to one side

72
Q

what catalyzes Williamson ether synthesis

A

base

73
Q

what catalyzes reverse of Williamson ether synthesis

A

acid

74
Q

what does a base and water do?

A

breaks ether, adds LG and OH

75
Q

what side cleaves when needed?

A

less hindered side

CHEM 246 (7 decks)

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