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GAMSAT Chemistry organic reaction pathways > 6. Alcohols > Flashcards

6. Alcohols Flashcards

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1
Q

what bonds can alcohols form

A

H bonds

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2
Q

are alcohols water soluble

A

the small ones are

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3
Q

-OH can act as a acid/base/both

A

both

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4
Q

what are the 5 ways alcohols can be prepared

A

alkyl halide hydrolysis

addition to alkene

hyboration-oxidation of alkene

aldehyde/ketone/ester reduction

grignard reagent

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5
Q

what reagents and reactants are involved when preparing alcohols via alkyl halide hydrolysis

A

RX + OH- (or H2O) -> ROH + X- (or HX)

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6
Q

When preparing alcohols via alkyl halide hydrolysis what reaction type of substitution occurs

A

Nucleophillic substitution

can be SN1 or 2

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7
Q

what reagents and reactants are involved when producing an alcohol from addition to alkene

A

H2O/H+

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8
Q

When preparing alcohols via addition to alkenes what reaction type of reaction mechanism occurs

A

SN1 and SN2 competes with E1 and E2

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9
Q

what reagents and reactants are involved when producing an alcohol from hydroboration oxidation of alkene

A

B2H6/H2O2 & OH- = prod primary alc

or

H2O & H+ = prod secondary alc

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10
Q

what reagents and reactants are involved when producing an alcohol from aldehyde/ketone/ester reduction

A

NaBH4 & H3O+ for aldehydes and ketones

LiAlH4 for esters

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11
Q

what reagents and reactants are involved when producing an alcohol from grignard reagent

A

aldehyde/ketone + RMgX/H3O+ = prod 2 and 3 alc respectively

ester/acid chloride + 2 equivalents RMgX/H3O+ = prod 3 alc

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12
Q

what are the 4 reactions alcohols undergo

A

nucleophilic substitution

elimination

oxidation

condensation

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13
Q

when an alcohol undergoes oxidation, what reagent or reactant is required to oxidise a primary alcohol

what is produced from using each type

A

H2CrO4/heat or H+/Cr2O7 2- = COOH

PCC = aldehyde

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14
Q

when an alcohol undergoes oxidation, what reagent or reactant is required to oxidise a secondary alcohol

what is produced

A

H2CrO4 = ketone

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15
Q

can a tertiary alcohol be oxidised

A

no

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16
Q

what reactants or reagents are required for alcohol to undergo elimination to form alkene

A

conc H2SO4/heat

17
Q

what do you get when you oxidise a primary alcohol with PCC

A

aldehyde

18
Q

what do you get when you oxidise a primary alcohol with H2CrO4/heat or H+/Cr2O7 2-

A

COOH

19
Q

what do you get when you oxidise a secondary alcohol with H2CrO4

A

ketone

20
Q

what is formed when an alcohol undergoes elimination with conc H2SO4/heat

A

alkene

21
Q

when alcohols undergo elimination with conc H2SO4/heat to form alkenes what mechanisms do primary alcohols react via

A

E2

22
Q

when alcohols undergo elimination with conc H2SO4/heat to form alkenes what mechanisms do secondary alcohols react via

A

E1/E2

23
Q

when alcohols undergo elimination with conc H2SO4/heat to form alkenes what mechanisms do tertiary alcohols react via

A

E1

24
Q

when a tertiary alcohol undergo nucleophilic substitution with conc HCl what is formed

A

tertiary alkyl halide

25
Q

what reagent or reactants are required to form tertiary alkyl halides from alcohols

A

tertiary alcohol react with conc HCl

26
Q

when a tertiary alcohol reacts with conc HCl to form tertiary alkyl halide what reaction mechanism does it react via

A

Sn1

27
Q

when a primary alcohol undergo nucleophilic substitution with SOCl2/pyridine what is formed

A

primary alkyl halide

28
Q

what reagent or reactants are required to form primary alkyl halides from alcohols

A

SOCl2/pyridine

29
Q

when a primary alcohol reacts with conc HCl to form tertiary alkyl halide what reaction mechanism does it react via

A

Sn2

30
Q

what pH is phenols and why is this

A

weak acid

delocalised charge

31
Q

what do e- withdrawing groups do to the acidity of phenols and why

A

increases acidity

stabilize phenoxide ion

32
Q

what do e- donating groups do to the acidity of phenols and why

A

decrease acidity

destabilize phenoxide ion

33
Q

what are examples of e- withdrawing groups for phenols

A

-CHO

-COOR

-X

34
Q

what are examples of e- donating groups for phenols

A

-OH

-NH2

35
Q

are aromatic alcohols stronger acids or are straight chain alcohols stronger

A

aromatic > straight chain

36
Q

what reagents or reactants are needed for condesation/esterification of alcohols

A

conc H2SO4/heat

alc and COOH or acyl chloride react

37
Q

what is produced when alcohols react with conc H2SO4/heat in the presence of COOH or acyl chlorides

A

esters

GAMSAT Chemistry organic reaction pathways (12 decks)

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