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O Chem 2 > Carboxylic Acids And Derivatives > Flashcards

Carboxylic Acids And Derivatives Flashcards

1
Q

What is the functional group of of an aliphatic acids?

A

COOH

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2
Q

What are fatty acids?

A

Long chain aliphatic acids

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3
Q

What is a carboxylic acids with 2 are called one?

A

Dioic acid

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4
Q

What is the carbon hybridization in the Formic acid?

A

Sp2

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5
Q

What are the bond angles in the resonance form of formic acid

A

120

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6
Q

Describe the chemistry of the dimers of carboxylate acids

A

2 molecules of carboxylic acids join to get ether by 2 hydrogen bonds ( 2 on OH to doubly bonded O)

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7
Q

Compare the boiling points of carboxylic acids to alcohols and alkanes

A

Boiling points substantially higher compared to alcohols and alkanes

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8
Q

What state are aliphatic acids of 8 carbons in room temperature?

A

Solids

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9
Q

What is the melting point of stearic acid(saturated)

A

72 degrees Celsius

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10
Q

What is the melting point of oleic acid( one cis double bond)?

A

16 degrees Celsius

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11
Q

What effect do double bonds have on melting points?

A

Lowers melting points

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12
Q

Between cus and trans which lowers melting points more?

A

Cis

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13
Q

What is the melting point of linoleic acid?

A

-5 degrees Celsius

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14
Q

Describe the structural differences and similarities in stearin, linoleic, oleochemicals acids

A

-All have 18 carbons

Stearic acid is saturated

Oleic acid has one cis double bond

Linoleic acid has 2 cis double bonds

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15
Q

How does length of carbon chain affect water solubility

A

Decreases water solubility

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16
Q

Which acids are miscible in water?

A

Acids with up to 4 carbons

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17
Q

Why are carboxylic acids soluble in non polar solvents?

A

Soluble in nonpolar solvents like chloroform because hydrogens of thedimer are not disrupted by the no polar solvent

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18
Q

What is the name of Ka

A

The acid dissociation constant

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19
Q

Compare carboxylic acids to phenols, alcohols and mineral acids in terms or acidity

A

Acids are weaker acids than mineral acids but stronger than alcohols and phenols

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20
Q

Explain why carboxylic acids are stronger acids than alcohols(in simplest terms)

A

Dissociation of a proton both break a hydroxyl group but in carboxylic acids, the carboxylate ions have a negative charge equally spread out over the 2 oxygen atoms

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21
Q

Whey are carboxylic acids much more acidic than alcohols?

A

An alkoxide ion has a localized negative charge on the oxygen atom.

A carboxylate ion has a negative charge spread out over both oxygen atoms.

This causes the carboxylate anion to have equivalent resonance structures, causing the carboxylate anion to be more stable than alkoxide ion and lower in energy and is present to a greater extent in equilibrium

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22
Q

How does distance affect a substituents affect ?

A

The bigger the distance from the carboxyl group, the smaller the effect

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23
Q

Which positions on an aromatic carboxylic acids yield for the highest substituent effects?

A

Ortho and para positions

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24
Q

Contrast electron-withdrawing groups and electron-donating groups in their effect on acidity

A

Electron-withdrawing groups- increase acidity

Electron-donating groups-decrease acidity

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25
Q

What happens alkyl benzene is reacted with hot potassium permanganate or hot chromic acid?

A

Alkyl benzene is oxidized to benzoic acid

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26
Q

How can alkanes be used to obtain a carboxylic acid?

A

Cleavage of an alkene with hot potassium permanganate can be used if there is a hydrogen on the double bonded alkene

27
Q

Alcohols and aldehydes are often oxidized to carboxylic acids using sodium dichromate and Sulfric acid. What is the resulting acid from this mixture.

A

Chromic acid(H2CrO4)

28
Q

Why is potassium permanganate used to oxidize alcohols and aldehydes to carboxylic acids less often than chromic acid?

A

The yields are often lower

29
Q

What happens when warm concentrated potassium dichromate is used to cleave alkene?

A

A glycol is formed by adding oxygen(cleaving the double bond) then either an carboxylic acid or ketone is formed depending on the original double bond

30
Q

How can alkanes be cleaved to give carboxylic acids?

A

Adding concentrated potassium permanganate

Or

Ozone and water

31
Q

How can the alkyl side chain of benzene be oxidized to a carboxylic acid?

A

Using one of 2 mixtures:

  1. Sodium dichromate, Sulfric acid and heat
  2. Potassium per Manganate, heat, water
32
Q

What is CO2 insertion?

A

Reacting CO2 with Grignard reagents and then protonating the resulting compound to form a carboxylic acid

33
Q

How can an organometallic compound be converted to a nitrile?

A

Addition of NaCN(sodium cyanide)

Acetone

34
Q

How can nitriles be converted to a carboxylic acid?

A

Water and presence of a proton from an acid

35
Q

What is saponification?

A

The basic hydrolysis of fats and oils to form soap

36
Q

How are fatty acids obtained?

A

From the hydrolysis of fats and oils

37
Q

Give 4 acid derivatives, names and functional groups

A
  • OH carboxylic acid
  • Cl, acid chloride
  • OR, ester
  • NH2, amide
  • OCOR, anhydride
38
Q

How do the 4 acid derivatives inter convert?

A

Using nucleophilic acyl substitution

39
Q

What is nucleophilic acyl substitution?

A

Reaction where one nucleophilic acyl substitution where nucleophile replaces another

40
Q

Why are carboxylic acids usually enhanced in reactivity for nucleophilic acyl substitution?

A

-OH is a poor leaving group

41
Q

How are carboxylic acids usually enhanced in reactivity for nucleophilic acyl substitution?

A
  1. Using a string acid catalyst to protonate the carboxyl and make it a better acceptor
  2. Converting the -OH into a better leaving group
42
Q

Compare and contrast nucleophilic addition reaction and nucleophilic Acyl substitution

A
  • both reactions begin with addition of a nucleophile to polar C=O to give a tetrahedral alkoxide intermediate
  • The intermediate formed from a ketone or aldehyde undergoes nucleophilic addition to be protonated to give an alcohol
  • Carboxylic acids undergo nucleophilic acyl substitution to form an intermediate that expels a leaving group to give a new carbonyl compound
43
Q

What kind of alcohol can be obtained from a carboxylic acid and how?

A

LiAlH4, lithium aluminum hydride reduces Carboxylic acids to yield primary alcohols

44
Q

Describe the reaction mechanism of the reduction of a carboxylic acid to an alcohol

A

First the hydroxyl group is replaced with a hydrogen to give an aldehyde intermediate

Then further reduced to give an alkoxideion(by breaking one of the bonds to the doubly bonded oxygen)

Finally it is protonated to give a primary alcohol

45
Q

How can a carboxylic acid be converted to an ester (Fischer esterification)

A

Heat the carboxylic acid with an acid catalyst(possibly HCl) while in an alcohol solvent

46
Q

What is the purpose of the acid in the Fischer esterification of a carboxylic acid?

A

Catalyst

Acts as a dehydrating agent , forcing the equilibrium to the right resulting in a greater yield of ester

47
Q

How can a carboxylic acids be converted to acid chlorides

A

Using treatment of thinner chloride (SOCl2) in order to prompt a nucleophilic acyl substitution reaction

48
Q

Describe the reaction mechanism (nucleophilic acyl substitution) where thionel chloride reacts with a carboxylic acid to form an acid chloride

A

Carboxylic acids first converted to an acyl chlorosulfate intermediate by replacing the hydrogen in OH to for, chlorosulfite

Chloride nucleophilic ion attacks the carboxylic carbon to form an acid chloride and sulfate

49
Q

How can carboxylic acids be used to form acid anhydrides?

A
  1. With pyridine in solution, carboxylic acids react with acid chloride to form an acid anhydride
  2. Best method is to prepare acid anhydrides nucleophilic acyl substitution between an acid chloride and carboxylic acids. This uses an ether catalyst and will be successful at 25 degrees Celsius
50
Q

What are amides?

A

Carboxylic derivatives where the hydroxyl group has been replaced with NH2, NHR, NR2

51
Q

Why are amides difficult to prepare using carboxylic acids and and substitution with amines

A

Amines are based which convert acidic carboxyl groups to their unreactive carboxylate form

52
Q

How and why are OH groups of activated to become a better non acidic leaving group to convert carboxylic acids to amides?

A

Why?-Amines convert carboxylic acids to carboxylate ions instead of undergoing nucleophilic acyl substitution

How- Carboxylic acids are usually treated with dicyclohexylcarboiimide(DCC) to activate it then addition of amide

53
Q

Aside from using carboxylic acids, how can amides be synthesized?

A

Acid chlorides can react with ammonia or amines to give amines and HCl

54
Q

Why are NaOH, Pyridine or a second equivalent of amine used when acid chlorides are used to synthesize amides?

A

To neutralize the HCl produced to prevent proton action of the amine

55
Q

Electron-withdrawing groups ___________ acid strength while electron donating groups ___________ acid strength.

A

Enhance

Decrease

56
Q

In what ways can carboxylic acids be synthesized?

A
  • oxidation of aldehydes and primary alcohols with chromic acid
  • Alkyl benzene oxidized to benzoic acid or hot chromic acid
  • cleavage of an alkene with hot KMNO4(oxidation) if there is a hydrogen on the double bond carbon
  • Carboxylation of Grignard reagents(Carbon dioxide insertion)
  • Hydrolysis of Nitriles
57
Q

How can carboxylic acids be synthesized from primary alcohols?

A

Use of chromic acids to convert to aldehydes then to carboxylic acids (KMNO4 can be used but yields are lower)

58
Q

An alkene be cleaved to give a glycol which converts to a carboxylic acid or ketone depending on the substitution of the original double bond. What chemical was added to the alkene?

A

Warm Concentrated KMNO4

59
Q

Give 2 ways alkynes can be used to synthesize a PAIR of carboxylic acids

A

Adding concentrated potassium permanganate to the alkyne( picture shows an internal alkyne)

Or

Ozone and water

60
Q

You have a bromoalkane, how can this be converted to a carboxylic acid?

A

First use magnesium and ether to convert it to a Grignard reagent

Secondly add carbon dioxide followed by a proton for protonation to convert the Grignard reagent to a carboxylic acid

61
Q

The ________ or ______ _________ of a nitrile produces a carboxylic acid

A

The basic

Acidic

Hydrolysis

62
Q

Aside from using carbon dioxide insertion after converting to a Grignard reagent, how else can an alkyl halide be converted to a carboxylic acid?

A

First add acetone and sodium cyanide

63
Q 
Out of the following aromatic carboxylic acids, give them in order of the acidity, strongest first:
P-methoxy benzoic acid 
M-nitro benzoic acid
P-nitro benzoic acid
O-nitro benzoic acid
Benzoic acid
A 
O-nitro benzoic acid
P-nitro benzoic acid
M-nitro benzoic acid
Benzoic acid
P-Methoxy Benzoic acid

O Chem 2 (22 decks)

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