6. Alcohols

Question 1

what bonds can alcohols form

Answer 1

H bonds

Question 2

are alcohols water soluble

Answer 2

the small ones are

Question 3

-OH can act as a acid/base/both

Answer 3

both

Question 4

what are the 5 ways alcohols can be prepared

Answer 4

alkyl halide hydrolysis

addition to alkene

hyboration-oxidation of alkene

aldehyde/ketone/ester reduction

grignard reagent

Question 5

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

Answer 5

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

Question 6

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

Answer 6

Nucleophillic substitution

can be SN1 or 2

Question 7

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

Answer 7

H2O/H+

Question 8

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

Answer 8

SN1 and SN2 competes with E1 and E2

Question 9

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

Answer 9

B2H6/H2O2 & OH- = prod primary alc

or

H2O & H+ = prod secondary alc

Question 10

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

Answer 10

NaBH4 & H3O+ for aldehydes and ketones

LiAlH4 for esters

Question 11

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

Answer 11

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

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

Question 12

what are the 4 reactions alcohols undergo

Answer 12

nucleophilic substitution

elimination

oxidation

condensation

Question 13

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

what is produced from using each type

Answer 13

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

PCC = aldehyde

Question 14

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

what is produced

Answer 14

H2CrO4 = ketone

Question 15

can a tertiary alcohol be oxidised

Answer 15

no

Question 16

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

Answer 16

conc H2SO4/heat

Question 17

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

Answer 17

aldehyde

Question 18

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

Answer 18

COOH

Question 19

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

Answer 19

ketone

Question 20

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

Answer 20

alkene

Question 21

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

Answer 21

E2

Question 22

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

Answer 22

E1/E2

Question 23

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

Answer 23

E1

Question 24

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

Answer 24

tertiary alkyl halide

Question 25

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

Answer 25

tertiary alcohol react with conc HCl

Question 26

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

Answer 26

Sn1

Question 27

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

Answer 27

primary alkyl halide

Question 28

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

Answer 28

SOCl2/pyridine

Question 29

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

Answer 29

Sn2

Question 30

what pH is phenols and why is this

Answer 30

weak acid delocalised charge

Question 31

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

Answer 31

increases acidity stabilize phenoxide ion

Question 32

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

Answer 32

decrease acidity destabilize phenoxide ion

Question 33

what are examples of e- withdrawing groups for phenols

Answer 33

-CHO -COOR -X

Question 34

what are examples of e- donating groups for phenols

Answer 34

-OH -NH2

Question 35

are aromatic alcohols stronger acids or are straight chain alcohols stronger

Answer 35

aromatic > straight chain

Question 36

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

Answer 36

conc H2SO4/heat alc and COOH or acyl chloride react

Question 37

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

Answer 37

esters