Chapter 13 Flashcards

1
Q

Reagents for deprotonating alcohols - to produce H2 gas

A

strong base

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2
Q

Reagents for deprotonating alcohols - to produce alkoxide ion

A

Li or
Na or
K

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3
Q

Factors affecting acidity of alcohols

A

resonance
induction
solvation effect

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4
Q

Factors affecting acidity of alcohols - resonance

A

resonance structures makes it more acidic

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5
Q

Factors affecting acidity of alcohols - induction

A

electron withdrawing of electronegative atoms increases stability, making more acidic

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6
Q

Factors affecting acidity of alcohols - solvation effects

A

sterically hindered solutions arent stabilised, so less acidic

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7
Q

Preparation of alcohols

A

made by substitution reactions

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8
Q

Preparation of alcohols - primary substrate

A

NaOH

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9
Q

Preparation of alcohols - tertiary substrates

A

H2O

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10
Q

Preparation of alcohols - secondary substrates

A

neither SN1 or SN2 is effective

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11
Q

Alcohol preparation from alkene - acid catalysed - reagents

A

dilute H2SO4

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12
Q

Alcohol preparation from alkene - acid catalysed

A

most substituted

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13
Q

Alcohol preparation from alkene - oxymercuration demurcation - reagents

A

Hg(OAc)
H2O
NaBH4

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14
Q

Alcohol preparation from alkene - oxymercuration demurcation

A

most substituted

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15
Q

Alcohol preparation from alkene - hydroboration - reagents

A

BH3.THF

H2O2 NaOH

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16
Q

Alcohol preparation from alkene - hydroboration

A

less substituted

17
Q

Preparation of alcohols via reduction

A

decreases oxidation state

reduces ketone or aldehyde to alcohol

18
Q

Preparation of alcohols via reduction - reagent 1

A

H2

Pt,Pd or Ni

19
Q

Preparation of alcohols via reduction - reagent 2

A

NaBH4

H2O, MeOH or EtOH

20
Q

Preparation of alcohols via reduction - reagent 3

A

1) LAH

2) H2O

21
Q

NaBH4 and LAH - double bonds

A

will not reduce the double bond

22
Q

LAH

A

will react with an ester or COOH to produce alcohol

23
Q

Diols preparation

A

prepared by excess reduction reagents or dihydroxylation of alkene

24
Q

Dihydroxylation of alkene - syn- reagents

A

OsO4

NMO

25
Q

Dihydroxylation of alkene - anti- reagents

A

RCO3H

H3O+

26
Q

Grignard reagant

A

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

27
Q

Grignard reaction - reagents

A

1) R-Mg-Br

2) H2O

28
Q

SN1 reactions with alcohols -

A

tertiary alcohols undergo substution when treated with hydrogen halide
racemixture

29
Q

SN2 reactions with alcohol

A

primary and secondary will undergo substitution reactions

gives inversion of configuration

30
Q

SN2 reagents - primary alcohols

A

HBr

HCL, ZnCl2

31
Q

SN2 reagents - tosylate

A

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

32
Q

SN2 reagents - primary and secondary

A

SOCl2 and pyridine

PBr3

33
Q

E1 and E2 reactions with alcohols

A

undergo elimination in acidic conditions

34
Q

E1 and E2 reactions with alcohols - reagents

A

H2SO4

heat

35
Q

Oxidations of alcohol - primary

A

produces aldehyde then COOH

36
Q

Oxidations of alcohol - secondary

A

produces ketone

37
Q

Oxidations of alcohol - tertiary

A

doesnt undergo oxidation

38
Q

Oxidations of alcohol - reagents

A

H2Cr2O4

39
Q

Oxidations of alcohol - to produce aldehydes

A

PCC

CH2CL2