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Semester 2 Chemistry Revisions > Lecture 12 > Flashcards

Lecture 12 Flashcards

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1
Q

Why do Carboxylic acids have a higher level of oxidation than ketones and aldehydes?

A

Carbon in the functional group of a carboxylic acid is bonded to 3 hetroatoms.

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2
Q

What are hetroatoms?

A

Atoms which are not bonded to hydrogen or carbon.

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3
Q

What is an aliphatic acid?

A

COOH is bonded to an ALKYL groupCOOH is bonded to an ALKYL group.

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4
Q

What is an aromatic acid?

A

COOH is bonded to an ARYL group.

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5
Q

Describe the reactivity difference between an aliphatic and aromatic acid?

A

Similar

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6
Q

What are long chain monocarboxylic acids called?

A

FATTY ACIDS

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7
Q

What hybrizisation is the carbon and oxygen in the carbonyl?

A

Sp2 Hybridised.

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8
Q

What is the bond angle of carbon/ oxygen?

A

120o

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9
Q

In the carboxylic acid functional group which two groups are eclipised?

A

O-H and C=O

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10
Q

IUPAC- How do you name a carboxylic:

i) aliphatic
ii) aromatic

A

LONGEST carbon chain with functional group named with parent alkane. Remove “e” and ADD “oic acid.”
Eg: Methane to Methanoic Acid
Aromatic carboxylic acids are named after the parent compound.
Eg: Benzene to Benzoic acid.

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11
Q

Common Naming- How do you name a carboxylic acid?

A

End in “ic acid”.
Eg: Methanoic Acid = Formic Acid.
Often derived from Latin or Greek word indicating original source.

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12
Q

IUPAC- How do you name an ester?

A

FIRST name the alky from the ALCOHOL –yl.
SECOND name is the ACID (with the C=O) -oate.
Split compound between (Single bond Oxygen) and (Double bond Oxygen).

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13
Q

Chemically- 2 Reagents and 1 Condition for the oxidation of primary alcohol or aldehyde to a carboxylic acid.

A

Reagents- KMnO4 & K2Cr2O7

Condition- Under reflux.

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14
Q

Biologically- Reagents and Cofactor needed for the oxidation of primary alcohol or aldehyde to a carboxylic acid.

A

ADH (alcohol dehydrogenase) Alcohol to Aldehyde
ALDH (aldehyde dehydrogenase) Aldehyde to Carboxylic Acid
NAD+/ NADP+- Accepts H that is lost

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15
Q

2 Reagents for the oxidation of a substituted aromatic?

A

KMnO4 & K2Cr2O7

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16
Q

Carboxylic Acids via Hydrolysis- Esters- Chemically- Reagent?

A

Acid/ Base

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17
Q

In Hydrolysis creating carboxylic acids chemically what happens when a base reagent is used?

A

Carboxylic acid salt is produced and so needs to be treated with protonation to get the acid out.

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18
Q

Carboxylic Acids via Hydrolysis- Esters- Biologically- Reagent?

A

Esterases.

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19
Q

When Carboxylic acids are created by Hydrolysis what mechanism is involved with nitriles?

A

NUCLEOPHILC SUBSTITUITION

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20
Q

When Carboxylic acids are created by Hydrolysis what is the reagents?

A

First Stage- NaCN

Second Stage- H3O+

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21
Q

When Carboxylic Acids are created via Condensation what is the chemical reagent used?

A

Grignard Reagent-

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22
Q

When Carboxylic Acids are created via Condensation what is the mechanism in the first step of this reaction called?

A

NUCLEOPHILIC ADDITION

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23
Q

Describe the chemical reaction in creating a carboxylic acid via condensation.

A
  1. NUCLEOPHILIC ADDITION, the nucleophile is the C in the Carbon Dioxide.
  2. ORGANIC carboxylic acid is produced.
  3. Reagent is BASIC so forms a metal salt which needs to be treated with acid to get rid of the metal.
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24
Q

When Carboxylic Acids are created via Condensation what is the biological reagent used?

A
  1. Rubsico and Biotin Dependent Carboxylases (Co-factor).
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25
Q

Describe the solubility of carboxylic acids.

A
  1. Similar to alcohols.
  2. Low molecular weight- hydrogen bonds so can dissolve in water.
  3. Basic conditions- carboxylic acids present as a SALT so can dissolve in water through ion- dipole interactions.
  4. Larger carboxylic acids not soluble in water- more hydrophobic forces.
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26
Q

Describe the boiling point of carboxylic acids.

A

Low molecular weight carboxylic acids have high boiling points because of STRONG intermolecular bonds.

27
Q

Because of a carboxylic acids boiling point what is created?

A

Dimers (Complex with 2 identical molecules linked together).

28
Q

Describe the odour of carboxylic acids.

A

Unpleasant odours.

29
Q

What pKa do Carboxylic acids have? What does pKa show about the acid?

A

High pKa- 4.8

How acidic an acid is so they are weak acids as they do NOT FULLY dissociate. .

30
Q

Why do Carboxylic acids behave differently to aldehydes/ ketones?

A

Carboxylic acid has an OH group which can leave.

31
Q

How do Carboxylic acids behave differently to aldehydes/ ketones?

A

Still undergo NUCLEOPHILIC ADDITION but C=O is REFORMED because that is more STABLE.

32
Q

What is the name of the reaction a Carboxylic acid undergoes when the mechanism is an Addition- Elimination reaction?

A

Condensation Reaction.

33
Q

Whats the difference between an Nucleophilic alpha substitution and a Nucleophilic Substitution?

A

Nucleophilic substitution takes place on a sp3 hybridized Carbon.

34
Q

What is needed to produce an acid chloride?

Reagent?

A

Carboxylic Acid

Add Cl- (SOCl2, PCl3, PCl5)

35
Q

Why are acid chlorides used than carboxylic acids?

A

Acid Chlorides are more reactive than carboxylic acids.

36
Q 
What is needed to produce an Ester?
What is the other product in this reaction?
Name of reaction?
Reagent?
Conditions?
A 
Carboxylic Acid 
Ester and Water
Esterification
Alcohol.
Heat- Alcohol is dissolved by the carboxylic acid.
37
Q

In amide formation- what Functional group does a reactant contain?
What are the two reagents? Why do you need them?

A

COOH
Glutamate synthase & ATP
Glutamate synthase is responsible for the coupling between the glutamate and ammonia. ATP ACTIVATES the carboxylic acid.

38
Q

What reagent is needed for the reduction of a Carboxylic acid to a Primary Alcohol?

A

Strong Reducing Agent- LiAlH4

39
Q

Describe how C-C bond is formed (Claisen Reaction).

A

1) The CO2 on the second molecule undergoes DECARBOXYLATION.
2) Leaves a nucleophilic carbon.
3) Undergoes NUCLEOPHILIC ADDITION with the =O on the first molecule.
4) The SCoA is a cofactor which transports the molecules.
5) There is a formation of a new C-C bond.

40
Q

What reaction is a reverse of the formation of C-C bond?

A

Decarboxylation.

41
Q

What does decarboxylation require? Why?

A

Beta- Carbonyl or Carboxyl group.

Acts as an electron acceptor.

42
Q

Why is decarboxylation important?

A

Glucose metabolism, fatty acid biosynthsis.

43
Q

Why is Nucleophilic Addition strange to occur on a Alkene?

A

Nucleophile is attracted to positive charge.
Alkenes usually high electron density.
Carboxylic acids draw electron density away from alkenes.

44
Q

What is the clinical relevance of conjugate addition?

A

Irreversible Kinases Inhibition/ Anti- Cancer drugs.

45
Q

Reaction for Acid Hydroylsis.

A

Ester + Water — Carboxylic Acid + Alcohol

46
Q

What happens in base Hydroylsis?

A

Esters react with bases to produce the salt of the carboxylic acid and an alcohol.

47
Q

Reagent for Ester + Water — Carboxylic Acid + Alcohol

A

Acid Catalyst

48
Q

Reagent for Base hydroylisis?

A

NaOH

49
Q

What are saturated fatty acids?

A

Fatty acids with NO carbon- carbon double bond.

50
Q

What are unsaturated fatty acids?

A

Fatty acid with at least 1 carbon- carbon double bond.

51
Q

Which unsaturated fatty acid is naturally occuring?

A

Cis Alkene

52
Q

If Cis alkenes are naturally occurring how do trans fatty acids occur?

A

Trans alkenes often occur from the HYDROGENATING of cis alkenes which allows the double bonds it isomerise.

53
Q

What end is the Omega Carbon on a Fatty Acid?

A

The TERMINAL end- Opposite end to the carboxylic acid.

54
Q

What Fatty acid is the precursor to many prostaglandins?

A

Arachidonic Acid

55
Q

3 Ways of Naming Fatty Acids

A
  1. C:D Carbon: Double Bonds)
    1. DELTA (Numbering from Carboxylic Acid).
    1. OMEGA counts the first double bond.
56
Q

Which fatty acid is most likely to be a liquid why?

A

Cis Alkenes- bends in the chains which means the chain move into U and C shapes.

57
Q

Describe a triglyceride. Function?

A

3 Long Chain Fatty Acids & Bodies LONG TERM STORAGE of fats.

58
Q

Describe a glycerophospholipid. Function?

A

1 Phosphate Group, Glycerol (Phosphodiester backbone- phosphate and amino acid) & 2 Fatty Acids & CELL MEMBRANES.

59
Q

Which part of a glycerophospholipid is hydrophobic/ hydrophilic and polar/ non polar.

A 
Head= Hydrophilic= Polar
Tail= Hydrophobic= Non Polar
60
Q

What are salts?

A

Sodium/ Potassium Salts of Fatty Acid.

61
Q

Which end of a salt dissolves in the grease and which points out so particles are dissolved in water.

A

Hydrophobic tails dissolve in dirt/ grease and polar heads point out so particles are soluble in water.

62
Q

What is a Bile Acid?

A

BIOLOGICAL derivative of a soap.

63
Q

How is bile acid produced? And where? Function.

A

Oxidation of cholesterol.
Liver
Bile Acid allows the absorption of fats/ fat soluble vitamins from the small intestine.

Semester 2 Chemistry Revisions (12 decks)

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