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Chem 30B > Alcohols > Flashcards

Alcohols Flashcards

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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

20
Q

does the conversion of -OH into -OTs undergo inversion

A

no

21
Q

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

A

turning a poor LG –> great LG

22
Q

Zaitsev’s rule

A

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

23
Q

what happens in the E1 mechanism

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

A

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

25
Q

what is the fourth reaction

A

conversion of ROH –> alkenes (acid-catalyzed dehydration)

26
Q

what mechanism do primary alcohols undergo in acid-catalyzed dehydration

A

E2

27
Q

what mechanism do secondary or tertiary alcohols undergo in acid-catalyzed dehydration

A

E1

28
Q

what are the precursors for epoxides

A

alkenes

29
Q

redox reactions

A

involves a transfer of electrons

30
Q

oxidation

A

loss of electrons

31
Q

reduction

A

gain of electrons

32
Q

oxidizing agents

A

perform oxidation upon another species
- they are reduced

33
Q

reducing agents

A

perform reduction on another species
- they are oxidized

34
Q

how do number of C-O bonds affect oxidation

A

greater C-O bonds = greater oxidation

35
Q

how do numbers of C-H bonds affect reduction

A

more C-H bonds = greater reduction

36
Q

what is the fifth reaction

A

oxidation of alcohols using chromic acid

37
Q

what are the three options for reagents for oxidation of alcohols using chromic acid

A
  1. K2Cr2O7/H2SO4, 2. CrO3/H2SO4, or KMnO4/OH-/heat
38
Q

what does a primary alcohol convert to in the oxidation of alcohols using chromic acid

A

first oxidizes to an aldehyde, then to a carboxylic acid

39
Q

what does a secondary alcohol form in the oxidation of alcohols using chromic acid

A

a ketone

40
Q

what does a tertiary alcohol form in the oxidation using chromic acid

A

no reaction

41
Q

what is the sixth reaction

A

the partial oxidation of primary alcohol

42
Q

what is the main characteristic of PCC

A

it is a mild oxidizing agent

43
Q

what does the partial oxidation of a primary alcohol with PCC form

A

an aldehyde

44
Q

when does a hydride shift occur

A

when there is a tertiary carbon next to a secondary carbocation

45
Q

when does a methyl shift occur

A

when there is a quaternary carbon with 1+ methyl groups next to a secondary carbocation

46
Q
A

Chem 30B (5 decks)

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