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CHEM 246 > EXAM 2 > Flashcards

EXAM 2 Flashcards

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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
what happens when you reacts CrO3 with secondary alcohol?
removes both Hs, turns single bond O to double bond
26
what happens when you react dess Martin and pyridine with primary alcohol?
yields aldehyde
27
what happens when you react dess Martin and pyridine with secondary alcohol
removes both Hs, turns single bond O to double bond
28
what reactants do you use for WilliamSon ether synthesis?
NaH and THF
29
what is the simplified rxn for WilliamSon ether synthesis?
ROH + R'X ---> R-O-R' + HX
30
in WilliamSon ether synthesis, which reactant is most hindered?
ROH (3º>2º>1º)
31
in WilliamSon ether synthesis, which reactant is least hindered?
RX
32
what reactant do you use for acidic cleavage?
HX
33
what is the simplified rxn for acidic cleavage?
R-O-R' --> ROH + R'X
34
what reactant should you use for reverse of acidic cleavage?
NaH
35
what are the most hindered in acidic cleavage?
ROH primary and secondary
36
what are the least hindered in acidic cleavage?
tertiary ROH
37
what reactant should you use to make an epoxide?
mCPBA
38
describe primary alcohol
carbon w/ OH, 2 H, 1 R
39
describe tertiary alcohol
carbon w/ OH, 3 R
39
describe secondary alcohol
carbon w/ OH, H, 2 R
40
how to name alcohol and phenols
number longest carbon chain by OH group, # substituents in ABC order, replace -e w -ol
41
a less hindered O atom is more/less stable?
more
42
more inductive effect more/less acidic?
more so more stable
43
what are weak acids that do not react with weak bases (like amines) and have limited rxns with things like NaOH?
alcohols
44
what is more acidic, phenol or alcohol?
PHENOL!
45
are phenols with electron withdrawing more/less acidic than phenol itself?
more
46
are phenols with electron donating more/less acidic than phenol itself?
less
47
What reactants do you need to go from RSH to R-S-R'?
NaH and R'X
48
What does NaH yield from RSH?
RS-
49
What does R'X yield from RS-?
R-S-R'
50
what reactants should you use for alkoxylmercuration rxn?
ROH, Hg(AC)2 and NaBH4
51
what happens when you react ROH, Hg(AC)2, and NaBH4 with an alkene?
breaks double bond, adds OR to most hindered and H to least hindered
52
what does mCPBA do?
breaks double bond, creates epoxide
53
what does NaOCH3 and H2O do to epoxide?
breaks epoxide and adds OH at primary, methyl on other side of O
54
what does HBr do to an epoxide?
breaks epoxide and adds OH at more hindered, removes O, Br at end of other C chain
55
what does HBr do to an epoxide w double bond on ring?
breaks epoxide and adds Br at more hindered, removes O, OH at end of other C chain
56
what does RBr do to episulfide?
breaks episulfide and adds Br at less hindered, methyl on other side of S
57
What does NaH?
takes away LG from one reactant, H from the other, and synthesizes the reactants
58
list ketone, carboxylic acid, and aldehyde in order of increasing strength and discuss reaction rate comparatively
ketone < aldehyde < carboxylic acid ketone fastest and weakest
59
What happens when Li oxidizes?
it is stronger so it cleaves and any O goes to OH
60
Grignard reactants do what?
add R (can be Cs) and OH
61
what happens when you use 2 equivalent Grignard reactants?
it removes the OR group first (goes through two rxns)
62
what are things that help prove more acidity?
lower pKa, more stable, more inductive, more EN
63
what does an acid and heat do?
removes OH and makes double bond on markovnikov
64
what will HBr do?
cleaves bond, forms OH on more hindered, Br on less hindered
65
what does CH3Br do to episulfide?
S to CH3 on more hindered, Br on less hindered
66
what kind of rxn uses NaH
WilliamSon
67
what does SOCl2 do?
replaces OH with Cl
68
what does PBr3 do?
replaces OH with Br
69
what do Na, BH4 do?
go to anti-markov
70
what do you need for Grignard rxn
C=O
71
what does ROH (Hg) do?
breaks double bond, adds ether to one side
72
what catalyzes Williamson ether synthesis
base
73
what catalyzes reverse of Williamson ether synthesis
acid
74
what does a base and water do?
breaks ether, adds LG and OH
75
what side cleaves when needed?
less hindered side

CHEM 246 (7 decks)

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