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Chemistry 101 COPY > Esterification and Oxidation > Flashcards

Esterification and Oxidation Flashcards

1
Q

What is the structure of an alkyl halide?

A

R-X

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2
Q

What does the reaction of an alkyl halide with Na(+)C(-)≡N produce?

A

A nitrile

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3
Q

What is the structure of a nitrile?

A

R-C≡N

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4
Q

What does the reaction of an alkyl halide with NaX produce?

A

A different alkyl halide R-X’

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5
Q

What two things can the reaction of an alkyl halide with Na(+)O(-)H produce?

A

An alkene

An alcohol

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6
Q

What two things does the reaction of an alkyl halide with RO(-)Na+ produce?

A

An alkene

An ether

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7
Q

What does the reaction of an alcohol with H2SO4 produce?

A

An alkene

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8
Q

What are three products that can be produced by alcohols?

A

Aldehydes/Ketones
Carboxylic Acids
Esters

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9
Q

What does the reaction of an alcohol with HX produce?

A

An Alkyl Halide

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10
Q

What is the structure for an alcohol?

A

R-OH

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11
Q

What does the reaction of an alkyl halide with H2O produce?

A

An alcohol

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12
Q

What does the reaction of an alkyl halide with R-OH produce?

A

An ether

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13
Q

What is the structure of an ether?

A

R-OR’

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14
Q

What does the reaction of an ether with HX produce?

A

An alkyl halide

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15
Q

What is Fisher esterification the process of?

A

Converting an alcohol into an ester

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16
Q

What is the mechanism of Fisher esterification?

A

Alcohol + carboxylic acid -> ester

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17
Q

How is the new bond formed in fisher esterification?

A

We need a nucleophile to be strong enough to attack a delta positive carbon
But alcohol is too weak and the sp2 carbon is not positive enough, so a catalyst is needed.

18
Q

Are alcohols strong or weak nucleophiles?

A

Weak nucleophiles

19
Q

What is the most common catalyst in Fisher esterification?

A

Sulfuric Acid H2SO4

20
Q

How do catalysts impact a reaction?

A

They make things more reactive by making them more charged.

21
Q

What is a unique aspect of Fisher esterification that occurs after nucleophilic attack?

A

There is an acidic and basic group on the same molecule, leading to intramolecular proton transfer.

22
Q

What occurs in the intramolecular proton transfer of Fisher esterification?

A

The hydrogen from the substituted oxygen moves to the OH group, turning it into water, which is a great leaving group.

23
Q

What occurs after water is formed in a Fisher esterification?

A

An elimination reaction (the reformation of a catalyst)

24
Q

Describe the elimination reaction in Fisher esterification.

A

The sulfonate anion wants gains a proton to become sulfuric acid again. Electrons from the OH bond are used to reform the double bond and the OH group leaves as water, forming an ester.

25
Q

Do all alcohols undergo oxidation?

A

No.

26
Q

What criteria must be satisfied in order for an alcohol to undergo oxidation?

A

It must have a hydrogen to lose.

27
Q

What two processes can occur through the oxidation of primary alcohols?

A

Primary Alcohol->Aldehyde (then potentially carboxylic acid)

Primary Alcohol->Carboxylic Acid

28
Q

What determines whether a primary alcohol will form an aldehyde or a carboxylic acid?

A

The oxidising agent used.

29
Q

What type of oxidising agent will form a carboxylic acid, rather than an aldehyde from an alcohol?

A

Oxidising agents that are strong enough that the aldehyde group is never isolated.

30
Q

What process occurs through the oxidation of secondary alcohols?

A

Secondary Alcohol->Ketone

31
Q

Do tertiary alcohols undergo oxidation?

A

No

32
Q

Why do tertiary alcohols not undergo oxidation?

A

As there is no C-H bond

33
Q

What oxidising agent is used to form an aldehyde from a primary alcohol?

A

Pyridinium chlorochromate (PCC in CH2Cl2)

34
Q

What two oxidising agents can be used to form a carboxylic acid from a primary alcohol?

A 
Chromium trioxide (CrO3) 
Sodium dichromate (Na2Cr2O7) in aqueous acid
35
Q

What two oxidising agents can be used to form a ketone from a secondary alcohol?

A 
Chromium trioxide (CrO3) 
Sodium dichromate (Na2Cr2O7) in aqueous acid
36
Q

What does the oxidation of a primary alcohol with Pyridinium chlorochromate (PCC in CH2Cl2) give as a product?

A

An aldehyde

37
Q

What does the oxidation of a primary alcohol with Chromium trioxide (CrO3) give as a product?

A

A carboxylic acid

38
Q

What does the oxidation of a primary alcohol with Sodium dichromate (Na2Cr2O7) in aqueous acid give as a product?

A

A carboxylic acid

39
Q

What does the oxidation of a secondary alcohol with Chromium trioxide (CrO3) give as a product?

A

A ketone

40
Q

What does the oxidation of a secondary alcohol with Sodium dichromate (Na2Cr2O7) in aqueous acid give as a product?

A

A ketone

Chemistry 101 COPY (32 decks)

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