Module 4: Core Organic Chemistry V1 Flashcards
Define what is meant by a “saturated compounds”
Has only single bonds and no C=C double/ multiple bonds. ✓
Define what is meant by a “Hydrocarbon”
Compound consisting of carbon and hydrogen atoms only ✓
Define what is meant by an “aliphatic compound”
Where the carbon atoms are joined together to form a straight chain. (branched or unbranched) ✓
Define what is meant by an “unsaturated compound”
Contains at least one carbon - carbon multiple bonds. ✓
Define what is meant by an “alicyclic compound”.
Where the carbon atoms are joined together in a ring structure. (branched or unbranched) ✓
Define what is meant by an “aromatic compound”
Compound which contains a benzene ring –C6H5 .✓
Classify the following molecules as being either:
a) Saturated or unsaturated
b) Aliphatic or alicyclic
c) Aromatic
Classify the following molecules as being either:
a) Saturated or unsaturated
b) Aliphatic or alicyclic
c) Aromatic
Note: the branch part is aliphatic
State the general formula for alkanes
Give the formula for an alkane containing 5 carbon atoms
Give the formula for an alkane containing 14 H atoms.
Systematically name the following:
2-methylbutane ✓ 2,2-dimethylpropane ✓
2,3,4-trimethylpentane ✓ 2,3,4,4-tetramethylhexane ✓
Systematically name the following:
Butane-1,3-diene ✓ Cyclopentane ✓
Cyclopentene ✓ Methylcyclohexane ✓
4,5,6,6-tetramethyloct-1-ene ✓
Systematically name the following:
1-bromo-2-fluoropropane ✓
bromochlorofluoroiodomethane ✓
1,1,2,2-tetrachloroethane ✓
2-chloro-3-methylbutane ✓
2-chloro-3-hydroxy-3-methylbutanoic acid ✓
5-hydroxypentanoic acid ✓
Draw the structure, using skeletal formula of the following compounds:
1. 2-bromopropane
2. 1,1,1-tribromopropan-2-ol
3. propanoic acid
4. butane-1,2-diol
5. 1,3-diiodopropane
6. 2-hydroxypropanoic acid
7. 2,3-dimethylhexanoic acid
8. 2-fluoro-3-iodobutanoic acid
9. cyclohexanol
10. 1,2-dichlorocyclopentane
11. 5. 3,4,5,6,7-pentamethyloctanoic acid
Give the structural formula for the following: 1. octane
2. ethanol
3. but-1-ene
4. propanoic acid
5. pentan-2-one
6. 2-bromopentane
7. hexanal
8. 2-methylpropene
Define what is meant by “structural isomers”
compounds with the same molecular formula… ✓ but different structural formulae ✓
Pentane is an isomer of 2-methylbutane. State and explain the type of isomerism between the two compounds.
Structural isomersim. ✓
Compounds with the same molecular formula… ✓
but different structural formulae ✓
Chain isomerism, ✓ where carbon chains can be branched or unbranched. ✓
butan-1-ol is an isomer of butan-2-ol. State and explain the type of isomerism between the two compounds.
Structural isomersim. ✓
Compounds with the same molecular formula… ✓
but different structural formulae ✓
Positional isomerism, ✓ where functional groups can be at a different position. ✓
propanone is an isomer of propanal. State and explain the type of isomerism between the two compounds.
Structural isomersim. ✓
Compounds with the same molecular formula… ✓
but different structural formulae ✓
Functional group isomerism, ✓ where functional groups can different. ✓
Hex-1-ene is an isomer of cyclohexane. State and explain the type of isomerism between the two compounds.
Structural isomersim. ✓
Compounds with the same molecular formula… ✓
but different structural formulae ✓
Functional group isomerism, ✓ where functional groups can different. ✓
Pen-1-yne is an isomer of cyclopentene and cyclopentane-1,3-diene. State and explain the type of isomerism between the three compounds.
Structural isomersim. ✓
Compounds with the same molecular formula… ✓
but different structural formulae ✓
Functional group isomerism, ✓ where functional groups can different. ✓
Draw the structure of all possible isomers of the following:
(note: naming them prevents you from making duplicate isomers, remember to follow the rules you don’t make mistakes i.e. “pentane vs 1-methylbutane”)
Draw the structure of all possible isomers of the following:
(note: naming them prevents you from making duplicate isomers, remember to follow the rules you don’t make mistakes i.e. “pentane vs 1-methylbutane”)
Draw the structure of all possible isomers of the following:
(note: naming them prevents you from making duplicate isomers, remember to follow the rules you don’t make mistakes i.e. “pentane vs 1-methylbutane”)
Draw the structure of all possible isomers of the following:
(note: naming them prevents you from making duplicate isomers, remember to follow the rules you don’t make mistakes i.e. “pentane vs 1-methylbutane”)
Draw the structure of all possible isomers of the following:
(note: naming them prevents you from making duplicate isomers, remember to follow the rules you don’t make mistakes i.e. “pentane vs 1-methylbutane”)
Draw the structure of all possible isomers of the following:
(note: naming them prevents you from making duplicate isomers, remember to follow the rules you don’t make mistakes i.e. “pentane vs 1-methylbutane”)
Draw the structure of all possible isomers of the following:
(note: naming them prevents you from making duplicate isomers, remember to follow the rules you don’t make mistakes i.e. “pentane vs 1-methylbutane”)
Draw the structure of all possible isomers of the following:
(note: naming them prevents you from making duplicate isomers, remember to follow the rules you don’t make mistakes i.e. “pentane vs 1-methylbutane”)
Determine the general formula for the following compounds (each row)
Note: You may wish to compare the pattern (change in molecular formula) to the alkanes general formula.
What is the number of alicyclic structural isomers of C5H10?
- Cyclopentane
- methylcyclobutane
- ethylcyclopropane
- 1,2-dimethylcyclopropane
- 1,1-dimethylcyclopropane
- ✓
The systematic name for halothane is 2-bromo-2-chloro-1,1,1-trifluoroethane.
Draw the structure of a halothane molecule.
✓
What is the number of fluorine atoms in 7.896 g of 2-bromo-2-chloro-1,1,1-trifluoroethane. Give your answer to 4 significant figures.
Explain why alkanes are generally unreactive.
Molecules are non-polar (no dipoles) ✓
C-C and C-H bonds have high bond enthalpies ✓
Define what is meant by a “sigma bond”
Caused by the end-on-end overlap of bonding orbitals ✓ directly between atoms ✓
State and explain the shape around the carbon atoms in a molecule of hexane. Include a bond angle in your answer.
Tetrahedral ✓
109.5 degrees ✓
There are 4 bonded pairs and 0 lone pairs around the C atoms ✓
All electron pairs repel ✓
Describe and explain how boiling points changes as carbon chain length in a straight chain alkane increases
As chain length/ number of carbon atoms increases ✓… boiling and melting points increases. ✓
Largermoleculeshave more points of surface contact between molecules. ✓
Strength of induced dipole-dipole interactions increases betweenmolecules, which requires more energy to overcome. ✓
Describe and explain how boiling point changes as the number of branches in an isomer molecule increases
Themorebranchesin anisomermolecule, the lower the boiling point ✓
The lesspointsofsurfacecontactwith each other… ✓
The weaker induced dipole-dipole interactions between molecules which require less energy to overcome ✓
Explain why decane has a higher boiling point than pentane
Decane has more carbon atoms. ✓
Decane is largerandhas more points of surface contact between molecules. ✓
Decane has stronger of induced dipole-dipole interactions increases between molecules, which requires more energy to overcome. ✓
Explain why 2,3-dimethylbutane has a lower boiling point than hexane
Hexane has less branches than 2,3-dimethylbutane but the same number of carbon atoms ✓
Hexane has morepointsofsurfacecontactbetween molecules ✓
Hexane has stronger induced dipole-dipole interactions between molecules which require more energy to overcome ✓
Write a balanced equation for the complete combustion of ethane
CHO
Write a balanced equation for the complete combustion of ethanol
CHO (don’t forget the O in ethanol)
Write a balanced equation for the complete combustion of octane
Write a balanced equation for the complete combustion of a mixture of ethanol and octane, where the ratio of ethanol: octane is 1:1
Explain why branched chain alkanes are preferred for fuels compared to straight chain alkanes
They have more efficient combustion ✓
State a hazard associated with carbon monoxide.
Carbon monoxide is poisonous ✓
Define what is meant by “complete combustion” and give the balanced equation for complete combustion of methane
Burning of a substance in excess supply of oxygen ✓
Define what is meant by “incomplete combustion” and give two balanced equations for incomplete combustion of methane. One to form CO and water only and another to form a solid product and water only.
burning of a substance in limited supply of oxygen ✓
Define what is meant a “radical”.
highly reactive species with an unpaired electron ✓
Define what is meant by “homolytic fission”.
Covalent bond breaks and one electron goes to each atom forming two radicals ✓
During radical substitution, in the initiation step, the type of bond fission taking place is homolytic fission. Explain why.
covalent bond breaks and one electron goes to chlorine atom forming two chlorine radicals ✓
Define what is meant by “heterolytic fission”.
Covalent bond breaks and both electrons go to the same atom forming two ions ✓
During the alkali hydrolysis of 2-bromopentane, the type of bond fission taking place in the C-Br bond is heterolytic fission. Explain why.
Covalent bond breaks and both electrons go to the bormine atom forming a bromine ion. ✓
Methane can be reacted with chlorine to form chloromethane. State the conditions required.
UV. ✓
High temperature. ✓
Methane reacts with chlorine by radical substitution.
Describe fully, with equations, the mechanism for this reaction.
Show all possible termination steps and include an overall equation in your answer.
Ethane reacts with chlorine by radical substitution.
Describe fully, with equations, the mechanism for this reaction.
Show all possible termination steps.
Bromomethane reacts with bromine by radical substitution.
Describe fully, with equations, the mechanism for this reaction.
Show all possible termination steps
Note: Starting material is bromomethane. you’re going to do substiution for the second time to make dibromomethane.
Cyclopentane reacts with chlorine by radical substitution
Describe fully, with equations, the mechanism for this reaction.
Show all possible termination steps
Ethanoic acid, CH3COOH reacts with bromine by radical substitution.
Describe fully, with equations, the mechanism for this reaction. Use structural formula only.
Show all possible termination steps
Note: You cannot susbtitute the carboxyl H.
Chlorine reacts with methane in the presence of UV. State the mechanism of this reaction and the bond fission taking place.
Free radical substitution. ✓
Homolytic bond fission. ✓
Iodine can react with methane in a substitution reaction. This reaction gives a mixture of products. How could the concentration of iodomethane in the final mixture be increased?
Excess methane ✓
Iodine can react with methane in a substitution reaction. This reaction gives a mixture of products. How could the concentration of tetraiodomethane in the final mixture be increased?
Excess iodine ✓
Propanoic acid can also react with bromine with a free radical substitution mechanism. Write the overall equation for this reaction, using molecular formula only.
Propanoic acid can also react with bromine with a free radical substitution mechanism. Draw the structure of both plausible radical intermediates in the propagation step.
Propanoic acid can also react with bromine with a free radical substitution mechanism. Draw the structure of all possible monosubstituted products
Note: Monosubstituted is where 1 H is swapped for 1 group/ halogen (in this case Br). You cannot swap the carboxyl H.
Cyclohexane, C6H12 can undergo free radical substitution with chlorine to form a mixture of products. Using skeletal/ displayed formula only, write an equation to show the formation of chlorocyclohexane.
Cyclohexane, C6H12 can undergo free radical substitution with chlorine to form a mixture of products. Using skeletal/ displayed formula only, write equations to show the mechanism for the reaction to form chlorocyclohexane only.
Cyclohexane, C6H12 can undergo free radical substitution with chlorine to form a mixture of products. Using skeletal/ displayed formula only, write equations to show all three possible termination steps.
State why UV radiation can be hazardous.
Can cause sunburn and skin cancer ✓
Using equations, explain how ozone is formed in the stratosphere and explain how it protects people from UV radiation.
What is a “Chlorofluorocarbon, CFC”
Compound containing chlorine, fluorine and carbon only where all hydrogens replaced ✓
State 4 properties of CFC’s
Stable ✓
volatile ✓
non-flammable ✓
non-toxic ✓
State 4 uses of CFC’s (in the past)
Aerosol cans ✓
dry cleaning ✓
air-conditioning ✓
fridges ✓
Dichlorodifluoromethane, CCL2F2, causes the breakdown of the ozone layer.
Using equations, describe how.
Include the initiation step, propagation steps and overall equation in your answer.
State the catalyst which catalyses the breakdown of Ozone.
Write equations to show how NO radicals destroy the ozone layer
State two sources of NO radicals in the stratosphere.
Aircraft engines ✓
Thunderstorms ✓
NO radicals destroy the ozone layer. Give the overall reaction equation.
R radicals destroy the ozone layer. Using equations show how. Include an overall equation in your answer.
OH radicals destroy the ozone layer. Using equations show how. Include an overall equation in your answer.
State and alternative to using CFC’s. Give an advantage and disadvantage to their use.
HCFC’s or HFC’s. ✓
HCFC’s are broken down in the atmosphere more quickly. ✓
HCFC’s and HFC’s are greenhouse gases. ✓
Alcohols can be synthesized from haloalkanes. State the reagents required and the name of the reaction taking place.
Warm aqueous NaOH or KOH ✓
Reflux ✓
Alkali hydrolysis ✓
1,2-dichloropropane reacts with warm aqueous KOH (under reflux) to form a diol. Draw a mechanism for the reaction, including a balanced equation.
How many σ-bonds and π-bonds are present in the following compounds
Using a labelled diagram, show how a π-bond is formed in ethene
Systematically name the following, including their stereoisomerism.
- (Z)-but-2-ene ✓
- (Z)-1,2-dibromo-1,2-dichloroethene ✓
(E)-1,2-dibromo-1,2-difluoroethane ✓
(Z)-3,4-dimethylhex-3-ene ✓
Note: you can use Cis/ Trans to describe these as there are two pairs of groups.
Draw and name the stereoisomers of 1-bromo-2-chloro-1-fluoro-2-iodoethene
Note: You can only use E/Z for naming as all groups are different.
Draw the stereoisomers of the following. If there are no E/Z isomers, state there are none
The molecule below has two double bonds, labelled 1 and 2.
The arrangement around each double bond can be identified as E or Z.
State the type of isomerism around double bond 1 and double bond 2
1: E ✓ and 2: E ✓
The following molecule shows E/Z isomerism.
Use the Cahn—Ingold—Prelog priority rules to identify whether this alkene is an E or Z
stereoisomer.
Explain how you came to your decision.
E Isomer. ✓
F takes priority over teh caron on the left hand side as it has a higher atomic number. ✓
CH2OH takes priority over the CH3 group on the right hand side. ✓
Complete the following diagram by adding products formed from the given reactions.
Systematically name the products.
Complete the following diagram by adding products formed from the given reactions.
Systematically name the products.
Complete the following diagram by adding products formed from the given reactions.
Systematically name the products.
Write an equations, including conditions and reagents above the arrow for the synthesis of 1,2-diiodopropane from propene using
a) skeletal formula
b) molecular formula.
Write an equations, including conditions and reagents above the arrow for the synthesis of propane from propene using
a) skeletal formula
b) molecular formula.
Write an equations, including conditions and reagents above the arrow for the synthesis of butan-2-ol from but-2-ene using
a) skeletal formula
b) molecular formula.
Write an equations, including conditions and reagents above the arrow for the synthesis of but-2-ene from 2-chlorobutane using
a) skeletal formula
b) molecular formula.
Write an equations, including conditions and reagents above the arrow for the synthesis of cyclohexanol from cyclohexane using
a) skeletal formula
b) molecular formula.
Write an equations, including conditions and reagents above the arrow for the synthesis of 1,2,3,4-tetraiodocyclopentane from cyclopentane-1,3-diene using
a) skeletal formula
b) molecular formula.
Draw a mechanism for the chlorination of but-2-ene, using curly arrows and partial charges.
State the type of bonding breaking taking place in the first step.
Name the reaction taking place.
Using partial charges and curly arrows, draw a mechanism for the for synthesis of 2-iodobutane from but-2-ene. Include a balanced equation (molecular formula) too.
Using partial charges and curly arrows, draw a mechanism for the for synthesis of 2,3-dibromobutane from but-2-ene. Include a balanced equation (molecular formula) too.
Using partial charges and curly arrows, draw a mechanism for the for synthesis of bromocyclohexane from cyclohexene. Include a balanced equation (molecular formula) too.
Using partial charges and curly arrows, draw a mechanism for the for synthesis of 1,2,3,4-tetrabromobutane from butane-1,3-diene. Include a balanced equation (molecular formula) too.
Using partial charges and curly arrows, draw a mechanism for the for synthesis of 1,1,2,2-tetrabromoethane from ethyne. Include a balanced equation (molecular formula) too.
For the following reactions, predict the major and minor products.
1. propene and steam
2. but-1-ene and steam
3. 2-methylbut-2-ene and HI
For the following reactions, predict the major and minor products.
For the following reactions, predict the major and minor products.
Write the equation, showing structures clearly, for the formation of the polymer poly(chloroethene)
Write the equation, showing structures clearly, for polymerisation of (E)-but-2-ene
The monomer phenylethene can be polymerised into poly(phenylethene).
Draw two repeating units of this polymer
Waste plastics can be burned, and the heat can be used to generate electricity. Toxic gases can be released from polymers containing chloride. This can be neutralised with sodium hydrogen carbonate to remove toxic gas formed.
Write an equation for the combustion of polychoroethene and another equation for the neutralisation of this gas.
Write an equation for the polymerisation of 1-bromo-1-fluoroprop-1-ene.
Draw two repeating units of the polymer formed from 2-methylbut-2-ene
Draw three repeating units of the polymer formed from 1,2-dichloroethene
For the following, give the structure of the monomer used to make the following polymers.
Name the monomer and polymer.
Complete the following synthesis map to show the product formed from each reaction. Include
The boiling points of 2-methylpropan-1-ol and butan-1-ol are shown below
Explain why the boiling points are different.
2-methylpropan-1-ol has less points of surface contact between molecules than butan-1-ol ✓
2-methyl propan-1-ol has weaker induced dipole-dipole interactions between molecules ✓
Which requires less energy to overcome ✓
The solubility of hexan-1-ol and hexane-1,6-diol in water is shown
Explain the difference in solubility of hexan-1-ol and hexane-1,6-diol
Hexane-1,6-diol has more OH groups ✓
Hexane-1,6-diol forms more hydrogen bondswith water ✓
Explain, with the aid of a diagram, why ethanol is soluble in water. Include relevant dipoles and lone pairs.
Write an equation for the combustion of propan-1-ol.
Write equations for the complete combustion of the following alcohols.
2-methylpropan-2-ol can be reacted with which reagents under what conditions to form 2-bromo-2-methylpropane? Name the type of reaction taking place.
Substitution. ✓
Write a balanced equation for the following reactions using
a) skeletal formula
b) molecular formula
Write a balanced equation for the following reactions using
a) skeletal formula
b) molecular formula
Ethene can be synthesized from an alcohol using what reagents and conditions? Name the reaction.
Dehydration ✓
Draw the product(s) from the elimination of propan-1-ol
Draw the product(s) from the elimination of pentan-2-ol
Hexan-3-ol can be reacted with sulfuric acid under reflux. Draw all possible compounds that could be formed.
The following alcohol is refluxed with sulfuric acid. Draw the product formed.
There is no product as there is no reaction. no H atoms attached to adjacent carbon atoms.
A student has two test tubes. One contains a primary alcohol and another contains a tertiary alcohol. Describe a suitable test to identify which test tube contains the primary alcohol.
A student has two test tubes. One contains a secondary alcohol and another contains a tertiary alcohol. Describe a suitable test to identify which test tube contains the secondary alcohol.
Describe why distillation is used in organic chemistry. Draw a labelled diagram for distillation aparatus.
Distillation is a separation technique ✓
Used to separate liquids with different boiling points and to prevent further reaction ✓
Describe why reflux is used in organic chemistry. Draw a labelled diagram for reflux aparatus.
Reflux – Used to react volatile substances together to prevent substances from escaping ✓
What reagents and contitions are required to oxidise a primary alcohol to an aldehyde (partial oxidation).
What reagents and contitions are required to oxidise a primary alcohol to an carboxylic acid (complete oxidation).
What reagents and contitions are required to oxidise an aldehyde to an carboxylic acid.
What reagents and contitions are required to oxidise a secondary alcohol to an ketone.
Either:
For the following reaction: Butan-2-ol and acidified potassium dichromate(VI) under reflux
a) Using skeletal formula, draw the balanced equation for the reaction. Include reagents and conditions above the arrow.
b) Using molecular formula, write a balanced equation for the reaction taking place.
For the following reaction: butan-1-ol and acidified potassium dichromate(VI) using distillation apparatus
a) Using skeletal formula, draw the balanced equation for the reaction. Include reagents and conditions above the arrow.
b) Using molecular formula, write a balanced equation for the reaction taking place.
For the following reaction: Butan-1-ol and acidified potassium dichromate(VI) under reflux
a) Using skeletal formula, draw the balanced equation for the reaction. Include reagents and conditions above the arrow.
b) Using molecular formula, write a balanced equation for the reaction taking place.
For the following reaction: Propanal and acidified potassium dichromate(VI) using reflux apparatus
a) Using skeletal formula, draw the balanced equation for the reaction. Include reagents and conditions above the arrow.
b) Using molecular formula, write a balanced equation for the reaction taking place.
A student is planning to synthesis 2,3-dimethylpentanal from 2,3-dimethylpentan-1-ol.
a) Write an equation for this reaction, using skeletal formula
b) Write an equation for this reaction, using molecular formula
c) State the reagents and conditions required for this reaction to take place
d) Draw a suitable apparatus for the synthesis
A student is planning to synthesis 2-methylpentanoic acid from 2-methylpentan-1-ol
a) Write an equation for this reaction, using skeletal formula
b) Write an equation for this reaction, using molecular formula
c) State the reagents and conditions required for this reaction to take place
d) Draw a suitable apparatus for the synthesis
Complete the equations below by balancing them and show the structures formed under the following conditions.
Complete the equations below by balancing them and show the structures formed under the following conditions.
Complete the equations below by balancing them and show the structures formed under the following conditions.
Complete the equations below by balancing them and show the structures formed under the following conditions.
Complete the following synthesis map adding products for each reaection.
A student is conducting an organic synthesis. They synthesize their product and are left with an impure liquid. Describe how they can purify the liquid using a separating funnel, which contains sulfuric acid, an alkene product and water.
Draw a diagram for this apparatus.
Products of a reaction and water is added to a separating funnel and the funnel is shaken and then allowed to settle. ✓
Less dense organic layer settles at the top. ✓
Water-soluble impurities dissolve in the lower aqueous layer ✓
Stopper is turned, aqueous layer is run off. ✓
Anhydrous MgSO4 or CaCl2 is used as a drying agent ✓
Drying agent can be removed by filtration once it settles to the bottom ✓
Complete the following synthesis map by drawing structres and adding reagents and conditions above the arrows.
Complete the following synthesis map by drawing structres and adding reagents and conditions above the arrows.
Complete the following synthesis map by drawing structres and adding reagents and conditions above the arrows.
*
Complete the following synthesis map by drawing structres and adding reagents and conditions above the arrows.
Complete the following synthesis map by drawing structres and adding reagents and conditions above the arrows.
Complete the following synthesis map by drawing structres and adding reagents and conditions above the arrows.
Complete the following synthesis map by drawing structres and adding reagents and conditions above the arrows.
X: Ethanol ✓
X: 2-methylpropan-1-ol ✓
A student plans to oxidise butan-2-ol to form butan-2-one using the apparatus shown in the diagram.
Give one reason why the apparatus is not suitable and describe a more suitable way of carrying out this oxidation.
Butan-2-ol/butanone is flammable
✓
Butan-2-ol / butanone has a low boiling point will evaporate ✓
What is the molecular formula of the following
