Chapter 13

Question 1

Reagents for deprotonating alcohols - to produce H2 gas

Answer 1

strong base

Question 2

Reagents for deprotonating alcohols - to produce alkoxide ion

Answer 2

Li or
Na or
K

Question 3

Factors affecting acidity of alcohols

Answer 3

resonance
induction
solvation effect

Question 4

Factors affecting acidity of alcohols - resonance

Answer 4

resonance structures makes it more acidic

Question 5

Factors affecting acidity of alcohols - induction

Answer 5

electron withdrawing of electronegative atoms increases stability, making more acidic

Question 6

Factors affecting acidity of alcohols - solvation effects

Answer 6

sterically hindered solutions arent stabilised, so less acidic

Question 7

Preparation of alcohols

Answer 7

made by substitution reactions

Question 8

Preparation of alcohols - primary substrate

Answer 8

NaOH

Question 9

Preparation of alcohols - tertiary substrates

Answer 9

H2O

Question 10

Preparation of alcohols - secondary substrates

Answer 10

neither SN1 or SN2 is effective

Question 11

Alcohol preparation from alkene - acid catalysed - reagents

Answer 11

dilute H2SO4

Question 12

Alcohol preparation from alkene - acid catalysed

Answer 12

most substituted

Question 13

Alcohol preparation from alkene - oxymercuration demurcation - reagents

Answer 13

Hg(OAc)
H2O
NaBH4

Question 14

Alcohol preparation from alkene - oxymercuration demurcation

Answer 14

most substituted

Question 15

Alcohol preparation from alkene - hydroboration - reagents

Answer 15

BH3.THF

H2O2 NaOH

Question 16

Alcohol preparation from alkene - hydroboration

Answer 16

less substituted

Question 17

Preparation of alcohols via reduction

Answer 17

decreases oxidation state

reduces ketone or aldehyde to alcohol

Question 18

Preparation of alcohols via reduction - reagent 1

Answer 18

H2

Pt,Pd or Ni

Question 19

Preparation of alcohols via reduction - reagent 2

Answer 19

NaBH4

H2O, MeOH or EtOH

Question 20

Preparation of alcohols via reduction - reagent 3

Answer 20

1) LAH

2) H2O

Question 21

NaBH4 and LAH - double bonds

Answer 21

will not reduce the double bond

Question 22

LAH

Answer 22

will react with an ester or COOH to produce alcohol

Question 23

Diols preparation

Answer 23

prepared by excess reduction reagents or dihydroxylation of alkene

Question 24

Dihydroxylation of alkene - syn- reagents

Answer 24

OsO4

NMO

Question 25

Dihydroxylation of alkene - anti- reagents

Answer 25

RCO3H | H3O+

Question 26

Grignard reagant

Answer 26

formed by reaction between alkyl halide and Mg involves introduction of R group cant be formed in presence of OH on the chain already

Question 27

Grignard reaction - reagents

Answer 27

1) R-Mg-Br | 2) H2O

Question 28

SN1 reactions with alcohols -

Answer 28

tertiary alcohols undergo substution when treated with hydrogen halide racemixture

Question 29

SN2 reactions with alcohol

Answer 29

primary and secondary will undergo substitution reactions | gives inversion of configuration

Question 30

SN2 reagents - primary alcohols

Answer 30

HBr | HCL, ZnCl2

Question 31

SN2 reagents - tosylate

Answer 31

alcohols can be converted to tosylate followed by nucleophilic attack TsCl Pyridine

Question 32

SN2 reagents - primary and secondary

Answer 32

SOCl2 and pyridine | PBr3

Question 33

E1 and E2 reactions with alcohols

Answer 33

undergo elimination in acidic conditions

Question 34

E1 and E2 reactions with alcohols - reagents

Answer 34

H2SO4 | heat

Question 35

Oxidations of alcohol - primary

Answer 35

produces aldehyde then COOH

Question 36

Oxidations of alcohol - secondary

Answer 36

produces ketone

Question 37

Oxidations of alcohol - tertiary

Answer 37

doesnt undergo oxidation

Question 38

Oxidations of alcohol - reagents

Answer 38

H2Cr2O4

Question 39

Oxidations of alcohol - to produce aldehydes

Answer 39

PCC | CH2CL2