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Semester 2 Chemistry Revisions > Lecture 12 > Flashcards

Lecture 12 Flashcards

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
Describe the solubility of carboxylic acids.
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.
26
Describe the boiling point of carboxylic acids.
Low molecular weight carboxylic acids have high boiling points because of STRONG intermolecular bonds.
27
Because of a carboxylic acids boiling point what is created?
Dimers (Complex with 2 identical molecules linked together).
28
Describe the odour of carboxylic acids.
Unpleasant odours.
29
What pKa do Carboxylic acids have? What does pKa show about the acid?
High pKa- 4.8 | How acidic an acid is so they are weak acids as they do NOT FULLY dissociate. .
30
Why do Carboxylic acids behave differently to aldehydes/ ketones?
Carboxylic acid has an OH group which can leave.
31
How do Carboxylic acids behave differently to aldehydes/ ketones?
Still undergo NUCLEOPHILIC ADDITION but C=O is REFORMED because that is more STABLE.
32
What is the name of the reaction a Carboxylic acid undergoes when the mechanism is an Addition- Elimination reaction?
Condensation Reaction.
33
Whats the difference between an Nucleophilic alpha substitution and a Nucleophilic Substitution?
Nucleophilic substitution takes place on a sp3 hybridized Carbon.
34
What is needed to produce an acid chloride? | Reagent?
Carboxylic Acid | Add Cl- (SOCl2, PCl3, PCl5)
35
Why are acid chlorides used than carboxylic acids?
Acid Chlorides are more reactive than carboxylic acids.
36
``` What is needed to produce an Ester? What is the other product in this reaction? Name of reaction? Reagent? Conditions? ```
``` Carboxylic Acid Ester and Water Esterification Alcohol. Heat- Alcohol is dissolved by the carboxylic acid. ```
37
In amide formation- what Functional group does a reactant contain? What are the two reagents? Why do you need them?
COOH Glutamate synthase & ATP Glutamate synthase is responsible for the coupling between the glutamate and ammonia. ATP ACTIVATES the carboxylic acid.
38
What reagent is needed for the reduction of a Carboxylic acid to a Primary Alcohol?
Strong Reducing Agent- LiAlH4
39
Describe how C-C bond is formed (Claisen Reaction).
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
What reaction is a reverse of the formation of C-C bond?
Decarboxylation.
41
What does decarboxylation require? Why?
Beta- Carbonyl or Carboxyl group. | Acts as an electron acceptor.
42
Why is decarboxylation important?
Glucose metabolism, fatty acid biosynthsis.
43
Why is Nucleophilic Addition strange to occur on a Alkene?
Nucleophile is attracted to positive charge. Alkenes usually high electron density. Carboxylic acids draw electron density away from alkenes.
44
What is the clinical relevance of conjugate addition?
Irreversible Kinases Inhibition/ Anti- Cancer drugs.
45
Reaction for Acid Hydroylsis.
Ester + Water --- Carboxylic Acid + Alcohol
46
What happens in base Hydroylsis?
Esters react with bases to produce the salt of the carboxylic acid and an alcohol.
47
Reagent for Ester + Water --- Carboxylic Acid + Alcohol
Acid Catalyst
48
Reagent for Base hydroylisis?
NaOH
49
What are saturated fatty acids?
Fatty acids with NO carbon- carbon double bond.
50
What are unsaturated fatty acids?
Fatty acid with at least 1 carbon- carbon double bond.
51
Which unsaturated fatty acid is naturally occuring?
Cis Alkene
52
If Cis alkenes are naturally occurring how do trans fatty acids occur?
Trans alkenes often occur from the HYDROGENATING of cis alkenes which allows the double bonds it isomerise.
53
What end is the Omega Carbon on a Fatty Acid?
The TERMINAL end- Opposite end to the carboxylic acid.
54
What Fatty acid is the precursor to many prostaglandins?
Arachidonic Acid
55
3 Ways of Naming Fatty Acids
1. C:D Carbon: Double Bonds) 2. 2. DELTA (Numbering from Carboxylic Acid). 3. 3. OMEGA counts the first double bond.
56
Which fatty acid is most likely to be a liquid why?
Cis Alkenes- bends in the chains which means the chain move into U and C shapes.
57
Describe a triglyceride. Function?
3 Long Chain Fatty Acids & Bodies LONG TERM STORAGE of fats.
58
Describe a glycerophospholipid. Function?
1 Phosphate Group, Glycerol (Phosphodiester backbone- phosphate and amino acid) & 2 Fatty Acids & CELL MEMBRANES.
59
Which part of a glycerophospholipid is hydrophobic/ hydrophilic and polar/ non polar.
``` Head= Hydrophilic= Polar Tail= Hydrophobic= Non Polar ```
60
What are salts?
Sodium/ Potassium Salts of Fatty Acid.
61
Which end of a salt dissolves in the grease and which points out so particles are dissolved in water.
Hydrophobic tails dissolve in dirt/ grease and polar heads point out so particles are soluble in water.
62
What is a Bile Acid?
BIOLOGICAL derivative of a soap.
63
How is bile acid produced? And where? Function.
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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