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CHY1101 - Organic chemistry > Oxidation > Flashcards

Oxidation Flashcards

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1
Q

What does a secondary alcohol oxidise to?

A

Ketone

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2
Q

What is the colour change when a secondary alcohol is oxidised?

A

Orange to green

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3
Q

What oxidising agent is used for alcohols?

A 
a chromium (6+ ) reagent 
Na2Cr2O7
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4
Q

Why is the oxidation of secondary alcohols a bad process?

A

Lots of Cr waste is generated

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5
Q

What alternative name does the oxidation of a secondary alcohol have?

A

Jones oxidation

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6
Q

How many chromate molecules are used in the Cr(VI) oxidation ?

A

2

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7
Q

What is the order of the oxidation states for the Cr(VI) oxidation mechanism?

A

Cr (VI)
Cr (IV)
Cr (III)

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8
Q

In the mechanism for the Cr (VI) oxidation, what is the key oxidising agent?

A

CrO3

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9
Q

What does a primary alcohol oxidise to initially?

A

Aldehyde

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10
Q

How does a primary alcohol oxidise to a carboxylic acid (final oxidation state)?

A

First it is oxidised to an aldehyde, then a water molecule is added which forms a hydrate (two OH), then the hydrate is oxidised to form the carboxylic acid

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11
Q

What is a jones reagent?

A

Reagent involved in the oxidation of primary and secondary alcohols

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12
Q

What type of reagent oxidises hydrates?

A

Jones reagents

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13
Q

Alcohols can be oxidised to aldehydes under basic conditions, what reagent would be used in this instance?

A

Pyridinium chlorochromate

PCC

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14
Q

Apart from basic, what other conditions would you need to use when using PCC?

A

Anhydrous

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15
Q

How are alkenes oxidised?

A

Through epoxidation
uses peracid RCO3H
C-O bonds form through syn addition

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16
Q

What type of reaction is synaddition, what does this mean?

A

Sn2

there will be an inversion of stereochemistry

17
Q

What are the issues with using Osmium Tetroxide?

A

Rare
Expensive
Sublimes straight to gas

18
Q

What are the issues with using Osmium Tetroxide for oxidation of alkene?

A

Rare
Expensive
Sublimes straight to gas

19
Q

What happens when osmium tetroxide is used for oxidation of alkene?

A

C-O bonds are formed in syn addition

Forms cyclic osmate ester through hydrolysis of the ester

20
Q

What is the product when you use osmium tetroxide to oxidise an alkene?

A

syn-1,2-diol

21
Q

What issues can Os (VI) cause?

A

Reduced to a metal so it forms a metal sheen across the eyeball if it comes close

22
Q

What type of osmium is needed for the catalytic version of oxidation of the alkene?

A

Only catalytic OsO4 is needed

23
Q

In the catalytic version using osmium tetroxide, what is the oxidising agent?

A

NMO

24
Q

In the catalytic version, what oxidation happens inside of the reaction?

A

Oxidation of Os (VI) back to Os (VIII)

25
Q

When using ozone to oxidise alkenes, what do you need to avoid using?

A

Oxidising agent as O3 is susceptible to oxidation

26
Q

When ozone is used to oxidise alkenes, which bond is formed?

A

C=O formed from C=C

27
Q

When ozone is used to oxidise alkenes, which bonds of the alkene are cleaved?

A

Pi and sigma bonds

28
Q

When ozone is used to oxidise alkenes, what reducing agent is used?

A

Dimelthylsulfide

29
Q

What is the product of oxidisation with ozone?

A

Aldehydes

30
Q

When ozone reacts with the alkene, what type of reaction is it?

A

concerted

as pi bond broken at the same time as its added

31
Q

When ozone reacts with the alkene, what type of addition is it?

A

Syn

32
Q

What cyclic product can be formed from ozone reacting with the alkene?

A

Ozonide

33
Q

What is formed when Me2S reacts with the cyclic ozonide?

A

It generates Me2SO and also 2 aldehydes

34
Q

Because Me2S is a mild reducing agent, what does it prevent?

A

Prevent the reduction of RCHO to alcohol and prevents the oxidation of RCHO to acid

35
Q

When oxidising alkenes with ozone, how do you make an alcohol your product instead of an aldehyde?

A

Use a stronger reducing agent

NaBH4

36
Q

When oxidising alkenes with ozone, how do you make an acid your product instead of an aldehyde?

A

Use an oxidising agent

H2O2

CHY1101 - Organic chemistry (22 decks)

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