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128 Cards in this Set

  • Front
  • Back

What type of molecule is this?

A phenol

What test can you use to prove something is a phenol?

Add Neutral Iron (III) Chloride to a sample of the substance. If a phenol group there will be a colour change of orange to purple.

Do alcohols turn Neutral Iron (III) Chloride purple?

No! Only phenols

What reagent will oxidise primary and secondary alcohols?

Acidified Dichromate (VI)

Name two types is molecules that can't be oxidised by Acidified Dichromate (VI)

Tertiary alcohols and phenols

What is Acidified Dichromate made of?

Sulfuric Acid and either Sodium Dichromate or Potassium Dichromate

What colour does Acidified Dichromate turn as a reaction occurs?

Orange > green


What functional group is this?

Ketone

What functional group is this?

Aldehyde

What functional group is this?

Carboxylic acid

How can you produce an aldehyde from a primary alcohol?

Partially oxidise it with Acidified Dichromate and relatively gentle conditions

How can you produce an aldehyde from a primary alcohol?

Partially oxidise it with Acidified Dichromate and relatively gentle conditions

How can you produce a carboxylic acid from a primary alcohol?

Fully oxidise it using Acidified Dichromate and severe conditions

How can you produce an aldehyde from a primary alcohol?

Partially oxidise it with Acidified Dichromate and relatively gentle conditions

How can you produce a carboxylic acid from a primary alcohol?

Fully oxidise it using Acidified Dichromate and severe conditions

How EXACTLY do you produce an aldehyde from a primary alcohol?

Add Acidified Dichromate to the primary alcohol and collect the aldehyde through distillation as it forms. It needs to be removed from the mixture otherwise it will be oxidised into a carboxylic acid.

How can you produce an aldehyde from a primary alcohol?

Partially oxidise it with Acidified Dichromate and relatively gentle conditions

How can you produce a carboxylic acid from a primary alcohol?

Fully oxidise it using Acidified Dichromate and severe conditions

How EXACTLY do you produce an aldehyde from a primary alcohol?

Add Acidified Dichromate to the primary alcohol and collect the aldehyde through distillation as it forms. It needs to be removed from the mixture otherwise it will be oxidised into a carboxylic acid.

How EXACTLY do you produce a carboxylic acid from a primary alcohol?

Add Acidified Dichromate to the primary alcohol and heat the mixture under reflux

How can you produce a carboxylic acid from an aldehyde?

Further oxidise it by heating it under reflux with Acidified Dichromate

How can you produce a carboxylic acid from an aldehyde?

Further oxidise it by heating it under reflux with Acidified Dichromate

How can you produce a ketone?

By heating a secondary alcohol under reflux with Acidified Dichromate

How can you produce a carboxylic acid from an aldehyde?

Further oxidise it by heating it under reflux with Acidified Dichromate

How can you produce a ketone?

By heating a secondary alcohol under reflux with Acidified Dichromate

Can you further oxidise a ketone?

No

How can you produce a carboxylic acid from an aldehyde?

Further oxidise it by heating it under reflux with Acidified Dichromate

How can you produce a ketone?

By heating a secondary alcohol under reflux with Acidified Dichromate

Can you further oxidise a ketone?

No

How can you tell if an alcohol is tertiary?

If Acidified Dichromate remains orange when mixed with the alcohol than it is tertiary

How can you tell a ketone and an aldehyde apart using Acidified Dichromate?

Is he Acidified Dichromate goes green when mixed with the compound that it's an aldehyde if it stays orange than it's a ketone. This is because aldehydes can be further oxidised using the Acidified Dichromate whereas ketones have been fully oxidised.

What is the name of this functional group?

Acyl chloridewhat

What more reactive: a carboxylic acid or an acyl chloride?

An acyl chloride. It is more reactive and corrosive.

What is the name of this functional group?

Acyl chloridewhat

What more reactive: a carboxylic acid or an acyl chloride?

An acyl chloride. It is more reactive and corrosive.

What's more reactive: a carboxylic or an acid anhydride?

Acid anhydrides

What's the definition of a 'Condensation' reaction?

The addition of two or more molecules to form a larger molecule, followed by the elimination of a small molecule, such as, water.

What functional group is this?

Ester

Name this molecule

ethylethanoate

What's the equation for producing an ester using an carboxylic acid?

alcohol + carboxylic acid > ester + water



Under reflux with concentrated sulfuric acid

The water produced in he production of a carboxylic acid and an alocohol is a...

By product

The water produced in he production of a carboxylic acid and an alocohol is a...

By product

What's the equation for the reaction of an alcohol and a acyl chloride?

alcohol + acyl chloride > ester + acid



Mix at RTP

What condition does the reaction of alcohol and an acyl chloride need to be under and why?

Anhydrous conditions because the acyl chloride would react with the water otherwise.

If possible why would you choose to use a carboxylic acid to produce an ester as opposed to a an acyl chloride?

Acyl chlorides are way more corrosive and the by-product of the reaction of an acyl chloride with with an alcohol is a acid whereas with a carboxylic acid it is water which is much less toxic and easy to dispose of.

What unsuspected functional group can acyl chloride react with to produce an ester?

Phenols! At RTP and under anhydrous conditions

What does a triplet peak indicate about an environment?

A triplet indicates that the carbon adjacent to the environment has 2H+ in addition to one hydrogen "n+1"

What does a broad peak around 3000 cm-1 ppm suggest on a mass spectrometry scale?

A carboxylic acid group

What does a broad peak around 3000 cm-1 ppm suggest on a mass spectrometry scale?

A carboxylic acid group

A student wanted to make a aldehyde from ethanol in the lab but and infrared spectrum suggested that the product was not made. What went wrong?

Aldehyde need to be oxidised in relatively gentle conditions with Acidified Dichromate and collected through distillation. If it is not collected like this then it will fully oxidise and become a carboxylic acid.

What does a broad peak around 3000 cm-1 ppm suggest on a mass spectrometry scale?

A carboxylic acid group

A student wanted to make a aldehyde from ethanol in the lab but and infrared spectrum suggested that the product was not made. What went wrong?

Aldehyde need to be oxidised in relatively gentle conditions with Acidified Dichromate and collected through distillation. If it is not collected like this then it will fully oxidise and become a carboxylic acid.

What functional group is present in Pentanoyl Chloride?

Acyl chloride

What is the name of this molecule?

Ethanoic Anhydride

What functional group represents an ester?

-C-(=O)O-C...

How do you produce an ester from an alcohol?

React an alcohol with a carboxylic acid with concentrated sulphuric acid whilst heating under reflux which produces an ester and water

How do you react phenols with carboxylic acids to form esters?

You can't. Carboxylic acids are less reactive than alcohols

How exactly do alcohols and carboxylic acids react to produce the product and the by-product?

The H lost from alcohol and the OH lost from carboxylic acid forming the water

How exactly do alcohols and carboxylic acids react to produce the product and the by-product?

The H lost from alcohol and the OH lost from carboxylic acid forming the water

What's the definition for a condensation reaction?

The addition of two or more molecules to form a larger molecule, followed by the elimination of a small molecule such as water

Discuss esterification in term of equilibrium

Esterification reaction is reversible so will reach equilibrium when in an enclosed system. Sulphuric acids absorbs the water so it will absorb the water produced during the condensation reaction so if conc. of water goes down then the system will react to replace it. So position of equilibrium will shift towards product side so a greater yield of ester produced.

What's more reactive: acyl chloride or carboxylic acid?

Acyl chloride

What's more reactive: acyl chloride or carboxylic acid?

Acyl chloride

How can you produce a ester from an acyl chloride and an alcohol?

Simply mix the two at RTP due reactivity of acyl chloride. Under anhydrous condition otherwise acyl chloride will react with water.

What's more reactive: acyl chloride or carboxylic acid?

Acyl chloride

How can you produce a ester from an acyl chloride and an alcohol?

Simply mix the two at RTP due reactivity of acyl chloride. Under anhydrous condition otherwise acyl chloride will react with water.

What does the reaction of an acyl chloride and an alcohol produce?

Ester + acid

What's more reactive: acyl chloride or carboxylic acid?

Acyl chloride

How can you produce a ester from an acyl chloride and an alcohol?

Simply mix the two at RTP due reactivity of acyl chloride. Under anhydrous condition otherwise acyl chloride will react with water.

What does the reaction of an acyl chloride and an alcohol produce?

Ester + acid

Carboxylic acid vs. Acyl chloride

- acyl chloride more corrosive, so hazardous.


- acyl chloride reaction produces acid not water which bad for environment - not a green by-product

Can an acid anhydride produce esters?

Yes. They react with alcohols or phenols producing esters and carboxylic acids.

What one bond breaks in a phenol when it reacts with an acid anhydride?

The H bond

Name some commonalities for acids

• they form solution with PH less than 7


• they turn universal indicator yellow/orange/red colour

Name some commonalities for acids

• they form solution with PH less than 7


• they turn universal indicator yellow/orange/red colour

Name some commonalities for alkalis (bases)

•form solutions with PH more than 7


• turn universal indicator purple/blue

What's the bronsted-Lowry definition of an acid?

A proton donor

According to the bronsted-lowry theory, what is a base?

A proton acceptor

According to the bronsted-lowry theory, what is a base?

A proton acceptor

According to the bronsted-lowry definition what is a proton?

A H+ ion (no electron so only a proton)

According to the bronsted-lowry theory, what is a base?

A proton acceptor

According to the bronsted-lowry definition what is a proton?

A H+ ion (no electron so only a proton)

H2O + NH3 > NH4* + OH-


What is the base and what is the acid?

Acid: H2O


Base: NH3

How does a carboxylic acid neutralise sodium hydroxide?

Acid + base > salt + water



The H comes off of the COOH and the O becomes negative attracting the positive Na and the OH- and the H+ combine to produce water. The Na and O combine like: O-Na+

How do acid neutralise weaker bases?

Acid + base > salt + water + carbon dioxide

Name this: CH3COO-Na+

Sodium ethanoate

What acid is stronger: phenol or carboxylic acid

Carboxylic acid

What acid is stronger: phenol or carboxylic acid

Carboxylic acid

How is a phenol an acid?

The hydroxyl group can donate its H+

What acid is stronger: phenol or carboxylic acid

Carboxylic acid

How is a phenol an acid?

The hydroxyl group can donate its H+

What are phenols unable to neutralise?

Weaker bases, e.g. Carbonates

Which of these (carboxylic acid, phenol, alcohol) react and neutralise sodium hydroxide?

Carboxylic acid and phenol. Alcohol is not strong enough so no reaction

Which of these (carboxylic acid, phenol, alcohol) react and neutralise sodium carbonate?

Carboxylic acid. The others will not. Base too weak for phenol.

Which of these (carboxylic acid, phenol, alcohol) react and neutralise sodium carbonate?

Carboxylic acid. The others will not. Base too weak for phenol.

When a carboxylic acid, phenol or alcohol reacts with neutral iron (III) chloride which will go from orange to purple?

The phenol - this is the specific test for phenol

What does 'hydrolysis' mean?

A reaction of a molecule with water. The water is used to break bonds in the molecule.

What does 'hydrolysis' mean?

A reaction of a molecule with water. The water is used to break bonds in the molecule.

When an ester is hydrolysed which products are produced?

Carboxylic acid and alcohol

How are condensation reactions and hydrolysis linked?

They are effectively the reverse of one another. Hydrolysis breaks and ester with water, whereas, condensation reaction produces an ester

During hydrolysis of an ester what bond will break?

The bond the between the


O - C of the ester functional group

During hydrolysis of an ester what bond will break?

The bond the between the


O - C of the ester functional group

Describe the conditions needed for hydrolysis to happen quickly?

Hydrolysis usually very slow so it is heated under reflux with a catalyst - either a dilute strong acid or a moderately conc. alkali

During hydrolysis of an ester what bond will break?

The bond the between the


O - C of the ester functional group

Describe the conditions needed for hydrolysis to happen quickly?

Hydrolysis usually very slow so it is heated under reflux with a catalyst - either a dilute strong acid or a moderately conc. alkali

Name a alkali that can be used as a catalyst for hydrolysis

NaOH

During hydrolysis of an ester what bond will break?

The bond the between the


O - C of the ester functional group

Describe the conditions needed for hydrolysis to happen quickly?

Hydrolysis usually very slow so it is heated under reflux with a catalyst - either a dilute strong acid or a moderately conc. alkali

Name a alkali that can be used as a catalyst for hydrolysis

NaOH

Acids and alkalis both work as catalysts for hydrolysis. Yet they work slightly differently. Explain the difference.

Acids work as expected they simply provide an a fast route for the reaction to take place producing the carboxylic acid and alcohol.


Alkalis work slightly differently. The carboxylic acid formed will be produced but then react with the alkali to form a salt.

During hydrolysis of an ester what bond will break?

The bond the between the


O - C of the ester functional group

Describe the conditions needed for hydrolysis to happen quickly?

Hydrolysis usually very slow so it is heated under reflux with a catalyst - either a dilute strong acid or a moderately conc. alkali

Name a alkali that can be used as a catalyst for hydrolysis

NaOH

Acids and alkalis both work as catalysts for hydrolysis. Yet they work slightly differently. Explain the difference.

Acids work as expected they simply provide an a fast route for the reaction to take place producing the carboxylic acid and alcohol.


Alkalis work slightly differently. The carboxylic acid formed will be produced but then react with the alkali to form a salt.

What will the salt look like after an ester has been hydrolysed with an alkali catalyst?

Back (Definition)

During hydrolysis of an ester what bond will break?

The bond the between the


O - C of the ester functional group

What's the difference between an ether and an ester?

An ether is an oxygen bonded between two carbons.


An ester is an oxygen bonded between two carbons but on one of those carbons is a double bond to another oxygen

When a molecules systematic name ends in '-anal' what functional group is present?

An aldehyde

When a molecules systematic name ends in '-anone' what functional group is present? And what does it look like?

A ketone. This is a carbon chain with a double bond oxygen to one of them

What will the salt look like after an ester has been hydrolysed with an alkali catalyst?

Back (Definition)

Name a alkali that can be used as a catalyst for hydrolysis

NaOH

What is the reaction showing?

The conversion of the salt produced after hydrolysing an ester with an alkali catalyst being converted back to a catalyst with the help of a strong acid.

What will the salt look like after an ester has been hydrolysed with an alkali catalyst?

Back (Definition)

Can you convert the salt the produced after the hydrolysis of an ester with an alkali back to a carboxylic acid? If so, how?

Yes. Add a strong acid, like, HCl it will p

What is the reaction showing?

The conversion of the salt produced after hydrolysing an ester with an alkali catalyst being converted back to a catalyst with the help of a strong acid.

When you see '-CHO' what functional group is present?

An aldehyde

CH3CH2OCH3 - what is this?

An ether

What is an ether?

An oxygen bonded between two carbons