CH6 : Alcohols Flashcards
General formula for alcohols?
CnH2n+1OH
What are primary,secondary and tertiary Alcohols?
Primary - when Carbon atom bonded to -OH group is attached to one other carbon
Secondary - the carbon atom bonded to the -OH group is attached to two other carbon atoms (or alkyl groups)
Tertiary - the carbon atom bonded to the -OH group is attached to three other carbon atoms (or alkyl groups)
Combustion of alcohols ?
Alcohol + oxygen —> CO2 + water
How do alcohols form chloroalkanes ? How can this reaction be used as a test for OH groups?
Reacting alcohols with PCl5 (phosphorus pentachloride) or HCl (chlorination)
Adding PCL5 = phosphoryl chloride (POCL3) / HCl /chloroalkane made
- adding PCl5 to unknown liquid is used as TEST - if HCl steamy fumes present , -OH group is present
Adding HCl - chloroalkane + water made
How can alcohols form bomoalkanes?
Bromination - react with compounds containing Br ions in substitution reaction (KBr)
- OH group replaced by Bromide
Requires catalyst (50% concentrate H2SO4- sulfuric acid)
Forms bromoalkane + water
How do alcohols form iodoalknes ?
React alcohol with phosphorous triiodide (PI3)
- PI3 is made in situ (within reaction mixture) by refluxing alcohol with ‘red phosphorus’ and iodine
Iodination - phosphoric acid (H3PO3) + iodoalkanes
Dehydration of Alcohols into alkenes?
Elimination reaction - water is eliminated
Heat alcohol with concentrated phosphoric acid (acid catalyst)
What oxidising agent is needed for the oxidation of alcohols?
- use oxidising agent (acidified potassium dichromate) - ORANGE
For potassium dichromate(VI) to act as an oxidising agent, it needs to be reduced
- reduction requires hydrogen (H+) ions which are provided by the acidic medium
When alcohols are oxidised the orange dichromate ions (Cr2O72-) are reduced to green Cr3+ ions
Oxidation of primary alcohols ?
Oxidised to form :
ALDEHYDES , which further oxidise into carboxylic acids
- use acidified potassium dichromate
ALDEHYDE - use excess alcohol with oxidising agent - aldehyde has lower BP than alcohol reactant so distilled off as soon as its formed
CARBOXYLIC ACID - alcohol is mixed with excess oxidising agent/heated under reflux - refluxed further
General formula and functional group of aldehydes and ketones?
Test for them?
Functional group - C=O
General formula - CnH2nO
Test: USE BENEDICT’S SOLUTION
if aldehyde : the blue copper ions reduced to brick red precipitate of copper oxide
If ketone : nothing happens
FEHLING’S SOLUTION
- contains copper ions dissolved in NaOH - act as oxidising agent
If aldehyde : aldehyde is oxidised to carboxylic acid
Colour change from BLUE TO RED
If ketone: nothing
Oxidation of sencodary alchols?
Ketones
- alcohol is heated under reflux with oxidising agent
Can’t be further oxidised so doesn’t need to be distilled straight after forming
Oxidation of tertiary alcohols?
Can’t be oxidised - only oxidised by burning them
- doesn’t react with potassium dichromate - stay ORANGE
Difference in structure between aldehydes and ketones?
Aldehyde : have a HYDROGEN and one ALKYL GROUP attached to carbonyl group (C=O)
Ketone: have 2 ALKYL GROUPS attached to carbonyl group
What is the purpose of heating under reflux?
When we want full oxidation
E.g Carboxylic acid from primary alcohol
Ketone from secondary alcohol
Any products of oxidation remain in reaction mixture - products boil off and condense /return to heating flask
What is difference between normal distillation and fractional distillation?
SIMPLE DISTILLATION: separate liquid and soluble solid - heated to BP of liquid
FRACTIONAL DISTILLATION: separate 2 or more liquids that are miscible - heated to BP of liquid with lower BP