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Organic chemistry > Carbonyl chemistry > Flashcards

Carbonyl chemistry Flashcards

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1
Q

What are the simplest carbonyl compounds?

A

Formaldehydes

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2
Q

What is resonsance?

A

Movement of electrons

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3
Q

The more resonance form a compound has the more stable it is. True or False?

A

True

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4
Q

The net charge between resonance forms stays the same. True or False?

A

True

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5
Q

What are the physical properties of carbonyls?

A

Polar
High Bp
Soluble in water

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6
Q

Why are the peaks located where they are?

A

This is because of bond strength, the stronger the bond strength the harder it is to pull, so higher the wavenumber

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7
Q

What is the IR spectrum wavenumber for carbonyl compounds C=O?

A

1600-1800

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8
Q

When conjugation occurs, more resonance is formed? True or False?

A

TRUE

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9
Q

What is conjugation?

A

Reduces carbonyl (double bond) characters

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10
Q

The larger the k value to more the equilibrium lies to the products and vice versa for smaller k value. True or False?

A

True

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11
Q

Bulkier carbonyls are more stable than bulkier normal alcohol groups due to steric hendrice. True or False?

A

True

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12
Q

What type of reactions do carbonyl compounds undergo under the reagents of water, cyanide and alcohols?

A

Nucleophilic addition.

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13
Q

What is the name of the intermediate that is obtained from a nucleophilic addition of carbonyls with cyanide ion?

A

Cyanohydrin

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14
Q

What is obtained when aldehydes and ketones react with alcohols?

A

Hemiacetyle - the aldehyde hemiacetyle is favoured because there less steric hendrice (less bulkier) than a ketone hemiacetyle.

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15
Q

What type of reactions does organometallic and grignard reagent perform with carbonyls?

A

Addition reactions

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16
Q

What do grignard and organometallic reagents provide during the nucleophilic addition?

A

Provide R-

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17
Q

Name the two steps involved when carbonyl is reacted with organolithium reagent?

A

Step 1- nucleophilic addition

Step 2- Protonation (using aqueous acid)

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18
Q

What are the two good R groups and X leaving groups?

A

Alkyl and Alkenyl

Cl, Br , I

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19
Q

Why is the carbonyl and organolithium reaction required in two steps?

A

Water will damage the organometallic/grignard reagent

20
Q

How are primary and secondary alcohols synthesised?

A

Aldehyde and organometallic reagent to produce primary alcohol or Aldehyde and grignard to produce secondary alcohols

21
Q

How are tertiary alcohols synthesised?

A

Ketone and organometallic reagent

22
Q

Give examples of functional groups that contain the C=O?

A 
Carboxylic acids 
Amides
Esters
Acid chloride
Acid anahydride
23
Q

What is the IR stretch of C=O in carboxylic acids and O-H stretch in carboxylic acids?

A

C=O 1710cm shifted by conjugation

O-H 3100cm (broad)

24
Q

What are the two peaks that acid anhydridres form and give reasoning to this?

A

1833 and 1767

Due to symmetrical and unsymmetrical stretching modes

25
Q

How can carboxylic be formed?

A

CO2 and grignard reagent - via nucleophilic addition and protonation using aqueous acid

26
Q

What is the firscher esterification reaction?

A

Craboxylic acid and alcohol to give water and ester

27
Q

What is the name of the reaction for fischer esterification?

A

Addition - elimination reaction

28
Q

How can you form an ester without breaking the C-O bond?

A

Using diazomethane to methylate the carboxylic acid and the carboxylic acid is then methylated to form the carboxylate anion whic via an Sn2 reaction will form an ester.

29
Q

What are the draw backs of using diazomethane?

A
  1. Toxic
  2. it only methylates acrboxylic acids
  3. Explosive
30
Q

What are the names of the reactions that occurs during methylation of carboxylic acid and formation of an ester?

A

Step 1- Deprotonation - a nucleophile and a methylating agent is formed
Step 2- Sn2 reaction to form an ester

31
Q

How many resonance forms does diazomethane have ?

A

3

32
Q

What is the process for obtaining amides from carboxylic acids?

A

Amine + carboxylic acid = ammonium salt

Ammonium salt + heat = Amide + H20

33
Q

What is the name of the second step in formation of amides from carboxylic acids?

A

Dehydration process

34
Q

How to form anhydrides from carboxylic acids?

A

Carboxylate anion + acid chloride = anhydride

35
Q

What reagent can be used to convert carboxylic acid to an acid chloride in formation of anydrides?

A

Thionyl chloride (SOCL2)

36
Q

What is the name of the reaction for converting COOH to Anhydride?

A

Addition - elimination?

37
Q

How do acyl groups defer from acids?

A

They have a good Cl leaving groups while acids have an OH group.

38
Q

Give examples of Acyl compounds?

A 
Esters
Acid chlorides 
Amides 
Anhydrides
Acid bromides
39
Q

What is the most important mechanism of acyl compounds?

A

Addition elimination reaction

40
Q

In addition elimination of acyl compounds, L is replaced but L can itself act as a nucleophile, therefore this is an equilibrium reaction. TRUE OR FALSE?

A

TRUE

41
Q

What are the physical properties of acyl compounds?

A

They can H bond and form dimers/ which gives them a high Bp

42
Q

Cl- are good leaving groups. True or False?

A

True

43
Q

With acid chloride reactions/ by product is always HCL. True or False?

A

True

44
Q

What do you get from reacting esters and organometallic reagents, with an addition elimination process?

A

Tertiary alcohols

45
Q

Esters and amides are more stable than aldehydes and due to greater resonance stabilization. True or False?

A

True

Organic chemistry (1 decks)

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