5 - What's in a Medicine? (WM) Flashcards by Nico Walker

Typical reactions of the OH group

-Can behave as acids
-Can react to form esters
-Can be oxidised by reaction with oxidising agents

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Acidity of the OH group

Least: Alcohols
Phenols
Most: Carboxylic acids

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Test for phenols

Use neutral iron (III) chloride

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What is the colour change for a phenol test if a phenol is present?

Solution will turn purple

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Reaction of OH group with weak base (Na2CO3)

-Will react with carboxylic acid only
-Produces salt, CO2 and water

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Reaction of OH group with strong base (NaOH)

-Will react with carboxylic acid and phenol
-Produces salt and water

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How is the OH group acidic?

OH group will be more acidic if the anion formed following dissociation is more stable

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What is the oxidising agent to oxidise alcohols?

Sodium dichromate

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What are the products for the oxidation of primary (1°) alcohols?

1: Aldehyde + Water
2: Carboxylic acid

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What are the products for the oxidation of secondary (2°) alcohols?

Ketone + Water (only one reaction)

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Can tertiary alcohols (3º) be oxidised?

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Describe primary (1º) alcohol

-Carbon bonded to 2 hydrogens
-1 R group

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Describe secondary (2º) alcohol

Only 1 hydrogen bonded
-2 R groups

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Describe tertiary (3º) alcohol

-No hydrogens bonded
-3 R groups

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pH of ethanol

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pH of phenol

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pH of salicylic acid

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pH of ethanoic acid

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Reaction of iron (III) chloride and ethanol

No change

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Reaction of iron (III) chloride and phenol

Turns purple

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Reaction of iron (III) chloride and salicylic acid

Turns purple

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Reaction of iron (III) chloride and ethanoic acid

No change

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Warming acidified dichromate with ethanol

Turned green

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Warming acidified dichromate with phenol

No change

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Warming acidified dichromate with salicylic acid

No change

Warming acidified dichromate with ethanoic acid

No change

Reacting sodium carbonate with ethanol

No change

Reacting sodium carbonate with phenol

No change

Reacting sodium carbonate with salicylic acid

Bubbling - CO2 produced

Reacting sodium carbonate with ethanoic acid

Bubbling - CO2 produced

Define functional group

Part of the molecule responsible for the way the molecule reacts. Also allow for differenciation of homologous series

General formula of alcohols

ROH

General formula of aldehydes

RCHO (double bond with O)

General formula of ketones

RCOR' (double bond with O)

General formula of carboxylic acids

RCOOH (double bond with 1 O)

General formula of acid anhydrides

(RCO)2O (double bond with 2 Os)

General formula of ethers

ROR'

General formula of esters

RCOOR' (double bond with 1 O)

General formula of phenols

Benzene ring and OH

Prefix/suffix of alcohols

-ol

Prefix/suffix of aldehydes

-al

Prefix/suffix of ketones

-one

Prefix/suffix of carboxylic acids

-oic acid

Prefix/suffix of acid anhydrides

-oic anhydride

Prefix/suffix of ethers

-oxy-

Prefix/suffix of esters

alkyl-____-anoate

Reaction forming ester with carboxylic acid and alcohol

Carboxylic acid + alcohol --> ester + water

What condition must be met to form an ester with a carboxylic acid and alcohol?

Sulfuric acid catalyst

Reaction forming ester with acid anhydride and alcohol

Acid anhydride + alcohol --> ester + carboxylic acid

How to name esters

-1st component comes from alcohol -2nd component comes from carboxylic acid

What ester is formed when reacting methanol and ethanoic acid?

Methylethanoate

How does infrared spectroscopy work?

-Radiation absorbed by bonds in molecules, only if it causes a change to their dipole moment -Results in different stretching and vibration -Amount of energy absorbed depends on mass of atoms and type of movement

How does mass spectrometry work?

-Molecules ionised to produce molecular ion (M+) -M+ accelerated and detected -Molecule can fragment and form a wide variety of fragments

How to read infrared spectra

-Give bond and wavenumber (data sheet) -More information given for further differenciation

How to read mass spectra

Give M+ peak and fragments

What is chromatography?

-Separates different compounds from mixtures -Checks purity -Reaction progress can be measured -Rf values can be compared -Compound's affinity for each phase influences the distance travelled

What does the Rf value represent?

Measure of how far compounds have travelled

Define stationary phase (chromatography)

What the compounds 'stick' to

Define mobile phase (chromatography)

What the compounds move through

What does affinity mean in the context of chromoatography?

Like dissolves like

How can the aldehyde product be separated in oxidation of alcohols?

Distillation

How can the carboxylic acid product be separated in the oxidation of alcohols?

Reflux

What is used to test for oxidation of alcohols?

Sodium dichromate

Positive test for oxidation with an alcohol and dichromate ions?

Colour change orange to green

Why is sulfuric acid used as a catalyst in many reactions?

Drying agent (removes water)

Define substitution reaction

Swapping functional group

Equation for elimination reaction of alcohols

Alcohol --> Alkene + H2O + H+

Conditions for elimination reactions of alcohols

- Al2O3 catalyst -Refluxed with concentrated H2SO4

1st step of elimination for alcohols

Curly arrow from O to H+ (outer electrons shown on O)

2nd step of elimination for alcohols

Curly arrow from bond C-O to O+ ion 2 Hs attached to O+

3rd step of elimination for alcohols

Curly arrow from C-H bond to C-C+ bond +H2O

4th step of elimination for alcohols

Alkene +H2O +H+ ion

Define nucleophile

Electron pair donor - can be ion or molecule

Define nucleophilic substitution

Type of substitution reaction in which a nucleophile is attracted to an electron deficient atom (Cδ+) where it donates a pair of electrons to form a new covalent bond

Reactants for nucleophilic substitution of alcohols

Alcohol & halogen

Equation for nuceleophilic substitution of alcohols

Alcohol + Halogen --> Haloalkane + H2O

1st step of nucleophilic substitution for alcohols

-Dipoles between C-O bond -Curly arrow from Cl- to C (C-O) -Curly arrow from C-O bond to H (OH)

2nd step of nucleophilic substitution for alcohols

Haloalkane +H2O