Chemistry - Whats in a Medicine

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What is the functional group of an Alcohol?
-OH (-ol)
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What is the functional group of an Aldehyde?
C; double bond O, single bond H (-al)
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What is the functional group of a ketone?
C=O (-one)
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What is the functional group of a Carboxylic Acid?
C; double bond O, single bond OH (-oic acid)
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What is the functional group of an Acid Anhydride?
O=C-O-C=O (double bond Oxygen's going down) (-oic anhydride)
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What is the functional group of an Ester?
C; double bond O, single bond O (-oate)
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What is the functional group of an Ether?
O (-oxy)
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Are Alcohol molecules polar? Why?
Yes - because of the polarised O-H bonds
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What dictates the physical properties of alcohols?
The -OH group dominates the physical properties of short chain alcohols
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What type of bonding is between alcohol molecules?
Hydrogen Bonding
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What does hydrogen bonding between alcohol molecules result in?
1) Higher melting points and boiling points that alkanes of comparable Mr; 2) Soluble in water
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How does solubility of alcohols in water change?
Solubility decreases as the carbon chain length increases and therefore more of the molecule is non-polar
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What are the three types of alcohols?
Primary, Secondary and Tertiary
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What does the type of alcohol depend on?
The position of the -OH group
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What is a Primary Alcohol (with Diagram)?
-OH bonded to a carbon bonded to one other carbon atom
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What is a Secondary Alcohol (with Diagram)?
-OH bonded to a carbon bonded to two other carbon atoms
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What is a Tertiary Alcohol (with Diagram)?
-OH bonded to a carbon bonded to three other carbon atoms
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How can the -OH (hydroxyl) group be oxidised?
With a strong oxidising agent like 'Acidified Potassium Dichromate (VI)- K2Cr2O7
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How does K2Cr2O7 oxidise?
1) Orange dichromate (VI) ion (CR207 2-) is reduced to green chromate (III) ions (Cr 3+); 2) The -OH group is converted into a carbonyl group (C=O); 3) Reaction turns from orange to green. - 2 atoms of hydrogen are removed, 1 from O & 1 from C.
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Why won't Tertiary Alcohols be oxidised?
Will not take place unless there is a hydrogen atom on the Carbon atom to which the -OH is attached to.
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What are Primary Alcohols oxidised to?
To aldehydes and then to Carboxylic Acids
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What is the word equation for the Oxidation of Primary Alcohols?
Primary Alcohol + Oxidising Agent -(Distillation)-> (Aldehyde +H20)) + (Oxidising Agent)-(reflux)-> Carboxylic Acid
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How to get an Aldehyde only from an Alcohol?
It can be distilled out of the reaction before it is oxidised further. Having alcohol in excess reduces the likelihood of the aldehyde being further oxidised
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What are Secondary Alcohols oxidised to?
To Ketones only
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How to oxidise Secondary Alcohols to Ketones?
Refluxing with excess oxidising agent. Ketones don't oxidise easily therefore oxidising for longer still won't produce more than a ketone.
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Do tertiary alcohols oxidise?
Do not oxidise - they do not have a hydrogen atom on the carbon atom to which the -OH group is attached.
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What is heating under reflux?
Safe Method for heating reactions involving volatile and flammable liquids. Liquid billed with a vertically mounted condenser so vapour condenses and returns back into the reaction mixture
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Tell me about Aldehydes (functional group)
Contains a carbonyl group (C=O) - at the end of the alkane chain
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Tell me about Ketones (functional group)
contains a carbonyl group (C=O) - within the alkane chain
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What does dehydration of an alcohol do?
You can make an alkene by eliminating the water from an alcohol
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How to dehydrate an alcohol?(Way 1)
Ethanol vapour passed over hot catalyst (pumice stone or Aluminium Oxide) - catalyst providing high Surface Area for reaction
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How to dehydrate an alcohol? (Way 2)
Reflux ethanol with excess concentrated sulphuric acid at 120 degrees celsius. Ethene then collected from water.
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Explain the mechanism of refluxing ethanol
Hydroxyl group bonds to H+ (Oxygen = +ve); +ve O pulls electrons away from neighbouring C and H20 fall off. Unstable carbocation created. Carbocation loses H+ and alkene is formed
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How do Alcohols turn into Halo alkanes?
Alcohols react with compounds containing halide ions in a substitution reaction. Hydroxyl groups is replaced by a halide, alcohol transformed into halo alkanes.
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What are the two ways of converting alcohols in esters?
1) Esterification using Acid Anhydride; 2) Esterification using a Carboxylic Acid
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What is Esterification?
A reaction between alcohol and Carboxylic Acids (and its derivatives)
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Outline the process of Esterification with Carboxylic Acids:
Heat an Alcohol with a Carboxylic Acid with acid catalyst (concentrated sulphuric or hydrochloric acid)
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Write out the equation for reaction between Carboxylic Acid and Alcohol
From Notes
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Outline the process of Esterification with Acid Anhydrides:
More reactive than Carboxylic Acids. React completely with alcohol giving a high yield of ester
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Write out the equation for reaction with Acid Anhydride and Alcohols:
From Notes
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What are ethers?
Same molecular formula as alcohols but different structure = structural isomers. Derived from alkanes by substituting an alkoxy group for a H atom.
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What is the General Formula of Ethers?
R-O-R
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How to name Ethers?
The longer hydrocarbon chain is chosen as parent alkane.
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What to use to purify liquid products?
Using a separating funnel; drying agents; simple distillation.
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What are examples of Carboxylic Acid derivatives?
Acid Anhydride and Esters
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Where does the -OH group occur?
Alcohols, phenol and Carboxylic Acids
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Where is the -OH group in phenols?
Attached to the Benzene ring in Phenols.
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General equation for reaction between -OH and water:
R-OH + H20 ----> R-O- + H3O+
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Reaction with -OH group and and ethanol?
Same reaction happens but to a lesser extent. Equilibrium lies further to the left and ethanol weaker acid than water.
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Reaction with -OH group and Phenols?
Equilibrium lies further to the right than water: Phenol slightly more acidic than water
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Reaction with -OH group and Carboxylic Acid?
Even more acidic - (but still a weak acid)
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Order of acid strength:
Ethanol
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What is formed when Carboxylic Acids react with Sodium Hydroxide
They are a strong enough acid. They react together to form salts.
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Describe the structure of Phenols:
A benzene ring with an -OH group attached to it.
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What is the general formula of Phenols?
C6H5OH - but other phenols have various groups attached to the benzene ring
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Briefly explain the Iron (III) Chloride Solution Test:
If you add a phenol to neutral iron (III) chloride solution and shake it, you get a purple solution.
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In Depth; explain the Iron (III) Chloride Solution Test:
Some atoms attracted to metal ions to form complexes, the -C=C-OH forms purple complex with Fe3+ ions in neutral solutions. Only phenols and its derivatives have this arrangement of atoms to give a colour with neutral iron (III) Chloride solution.
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Explain how Phenols react with Strong Acids:
1) Phenols dissolve in water to form a phenoxide ion and H+ ion (the solution is weakly acidic); 2) Phenols react with alkalis to produce a salt and water: Phenol + Sodium Hydroxide Solution -> Sodium Phenoxide + Water
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Do Phenols react with Carbonate Solutions?
They do not - Sodium Carbonate not strong enough base to remove hydrogen ion from phenol. Good way to tell apart phenols from carboxylic acids because carboxylic acids react with Carbonate Solutions but Phenols do not.
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Describe how Phenols react with Acid Anhydrides to form Esters:
Phenols react with Acid Anhydride to form Esters and Carboxylic Acid. Phenols will not react with Carboxylic Acid
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How does Infrared Spectroscopy affect covalent bonds?
It causes covalent bonds to vibrate
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How to identify an alcohol from an absorption peak of O-H bond:
1) Very Broad peak between 2500-3300 means Carboxylic Acid; 2) A broad peak between 3200-3550 symbolises an alcohol
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How to identify an aldehyde or ketone from absorption peak of C=O bond:
Peak between 1640-1750 symbolises Aldehyde, Ketone, Carboxylic Acid or Ester
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How to identify a Carboxylic Acid from absorption peak of C=O bond and broad peak from O-H bond
Peak between 1640-1750 for C=O bond; and broad peak between 2500-3300 = Carboxylic Acid
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What is Mass Spectroscopy used for?
To find out the atomic mass of its element and the relative abundances of isotopes in an element
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what is a Mass Spectrum produced by?
a Mass Spectrometer
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how does a Mass Spectrometer work?
1) Substance inserted into the Spectrometer; 2) Molecules then converted into ions; 3) Ions propelled into mass analyser; 4) Ions separated from mass:charge ratio; 5) Ions are detected and a mass spectrum is generated
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what is the M peak
the second to last peak; This is the Mr of the compound
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what is the M+1 peak
this is the last tiny peak - this is the last peak due to presence of carbon 13
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what is a mass spectrum (essentially)?
a fingerprint to the molecule that can be identified by a computer using spectral analysis
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what are common fragments in Mass Spectroscopy?
cH3+; C2H5+; CH3CH2CH2+: OH+
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what is the molecular mass of CH3+?
15
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what is the molecular mass of C2H5+?
29
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What is the molecular mass of CH3CH2CH2+?
43
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what is the molecular mass of OH+?
17
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what are the principles of Green Chemistry (1-8)?
better atom economy; Prevention of waste products; Less hazardous chemical synthesis; Design safer chemical product; Use safer solvents; Low energy usage; Use renewable feedstock; Reduce reagents used and the number of steps
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what are the principles of Green Chemistry (9-12)?
use catalysts and more selective catalysts; Design chemical products for degradation; Employ real time process monitoring; Use safer chemical processes.
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what is Thin Layer Chromatography?
used to separate small quantities of organic compounds; purify or check purity. Carried out on a silica plate.
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why must a suitable solvent be used in Thin Layer Chromatography?
different Organic Compounds have different affinities for solvents and will be carried through at different rates.
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Other cards in this set

Card 2

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What is the functional group of an Aldehyde?

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C; double bond O, single bond H (-al)

Card 3

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What is the functional group of a ketone?

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Preview of the front of card 3

Card 4

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What is the functional group of a Carboxylic Acid?

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Card 5

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What is the functional group of an Acid Anhydride?

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