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Chem 30B > Alcohols > Flashcards

Alcohols Flashcards

(56 cards)

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1
Q

what are the precursors for ethers

A

alkoxides

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2
Q

what happens when an alcohol is a base?

A

it gains a proton to form oxonium

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3
Q

what happens when alcohol is an acid?

A

it gains a proton and forms alkoxide

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4
Q

what is the main characteristic of a good leaving group?

A

weak bases

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5
Q

what are the best leaving groups?

A

I- > Br- > Cl- ~ H20

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6
Q

what reagent is needed to convert ROH –> Haloalkane

A

binary acid

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7
Q

what is the purpose of converting ROH into a haloalkane?

A

turns a bad leaving group into a great leaving group

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8
Q

what is the mechanism for conversion of ROH –> haloalkane for a primary alcohol

A

proton transfer, then Sn2

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9
Q

what is the mechanism for conversion of ROH –> haloalkane for a secondary/tertiary alcohol

A

proton transfer, then Sn1 mechanism

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10
Q

what connectivity do carbocations have

A

sp2, trigonal planar

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11
Q

what of product is generally formed from Sn1 attack

A
  • 50/50 mix of stereoisomers if chiral
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12
Q

what is reaction 1

A

conversion of ROH –> haloalkane with HX

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13
Q

what is the second reaction

A

conversion of ROH –> haloalkanes w/o use of HX

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14
Q

what reagents can you use for conversion of ROH –> haloalkane w/o use of HX

A

PBr3, thionyl chloride + pyridine

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15
Q

what is the mechanism for conversion of ROH –> haloalkanes w/o HX

A

Sn2
- effective with methanol, primary, and secondary alcohols only

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16
Q

which mechanism results in inversion of product

A

Sn2

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17
Q

what is the third reaction

A

conversion of ROH into aryl/alkyl

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18
Q

what reagent does conversion of ROH into aryl/alkyl sulfonates require

A

TsCl

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19
Q

what mechanism does ROTs undergo

A

Sn2

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20
Q

does the conversion of -OH into -OTs undergo inversion

A

no

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21
Q

what is the point of converting ROH into aryl/alkyl sulfonate

A

turning a poor LG –> great LG

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22
Q

Zaitsev’s rule

A

the major product of beta-elimination is the most stable alkene = the most substituted alkene

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23
Q

what happens in the E1 mechanism

Study These Flashcards
A

LG leaves first, forming a carbocation intermediate
- just like Sn1 but a double bond is formed

24
Q

what happens in the E2 mechanism

Study These Flashcards
A

no carbocation intermediate forms, bond events occur simultaneously
- just like Sn2

25
what is the fourth reaction
conversion of ROH --> alkenes (acid-catalyzed dehydration)
26
what mechanism do primary alcohols undergo in acid-catalyzed dehydration
E2
27
what mechanism do secondary or tertiary alcohols undergo in acid-catalyzed dehydration
E1
28
what are the precursors for epoxides
alkenes
29
redox reactions
involves a transfer of electrons
30
oxidation
loss of electrons
31
reduction
gain of electrons
32
oxidizing agents
perform oxidation upon another species - they are reduced
33
reducing agents
perform reduction on another species - they are oxidized
34
how do number of C-O bonds affect oxidation
greater C-O bonds = greater oxidation
35
how do numbers of C-H bonds affect reduction
more C-H bonds = greater reduction
36
what is the fifth reaction
oxidation of alcohols using chromic acid
37
what are the three options for reagents for oxidation of alcohols using chromic acid
1. K2Cr2O7/H2SO4, 2. CrO3/H2SO4, or KMnO4/OH-/heat
38
what does a primary alcohol convert to in the oxidation of alcohols using chromic acid
first oxidizes to an aldehyde, then to a carboxylic acid
39
what does a secondary alcohol form in the oxidation of alcohols using chromic acid
a ketone
40
what does a tertiary alcohol form in the oxidation using chromic acid
no reaction
41
what is the sixth reaction
the partial oxidation of primary alcohol
42
what is the main characteristic of PCC
it is a mild oxidizing agent
43
what does the partial oxidation of a primary alcohol with PCC form
an aldehyde
44
when does a hydride shift occur
when there is a tertiary carbon next to a secondary carbocation
45
when does a methyl shift occur
when there is a quaternary carbon with 1+ methyl groups next to a secondary carbocation
46
what is Br- good for
good nucleophile
47
what is I- good for
good nucleophile
48
what is CH3S- good for
good nucleophile
49
what is RS- good for
good nucleophile
50
what is HO- good for
good nucleophile
51
what is CH3O- good for
good nucleophile
52
what is RO- good for
good nucleophile
53
what is R-alkyne - good for
good nucleophile
54
what is CN- good for
good nucleophile
55
what is N3- good for
good nucleophile
56
what is H2N- good for
good nucleophile

Chem 30B (5 decks)

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