Module 4: Core Organic Chemistry V1 Flashcards by Shakir Uddin

Q

Define what is meant by a “saturated compounds”

A

Has only single bonds and no C=C double/ multiple bonds. ✓

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Q

The polymer, poly(pent-2-ene) has a relative molecular mass of 50,000. Calculate the number of monomer molecules required to make one molecule of the polymer.

A

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Q

State whether the following are an E or Z isomer AND/OR a Cis or a trans isomer.

A

Note: The last one is not a mistake.

Cis/ Trans needs atleast one pair. E/Z based on atomic number.

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Q

Complete the following diagram by adding products formed from the given reactions.

A

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Q

Complete the following diagram by adding products formed from the given reactions.

A

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Q

Showing organic structure only, complete and balance the following equation.

A

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Q

Showing organic structure only, complete and balance the following equation.

A

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Q

Cyclic alcohol’s A, B and C can be synthesised by the following reactions.

Complete the following synthesis map adding conditions and reagents in the boxes provided.

A

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Q

Showing organic structure only, complete and balance the following equations.

A

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Q

Showing organic structure only, complete and balance the following equations.

A

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Q

Define what is meant by a “Hydrocarbon”

A

Compound consisting of carbon and hydrogen atoms only ✓

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Q

Define what is meant by an “aliphatic compound”

A

Where the carbon atoms are joined together to form a straight chain or a cycle (branched or unbranched) and does not contain a benzene ring. ✓

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Q

Define what is meant by an “unsaturated compound”

A

Contains at least one carbon - carbon multiple bonds. ✓

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Q

But-1-ene can react with iodine monochloride, ICl.
The table shows Pauling values for some halogens.
Using the table attached, outline a mechanism for the reaction to form the major product only.
Include curly arrows, relevant dipoles and the structures of the intermediate and final product(s).

A

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Q

Define what is meant by an “alicyclic compound”.

A

Where the carbon atoms are joined together in a ring structure. (branched or unbranched) ✓

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Q

Define what is meant by an “aromatic compound”

A

Compound which contains a benzene ring –C6H5 .✓

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Q

Classify the following molecules as being either:
Saturated or unsaturated
Alicyclic
Aromatic or aliphatic (or both)

A

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Q

Classify the following molecules as being either:
a) Saturated or unsaturated
b) Aliphatic or alicyclic
c) Aromatic

A

Note: the branch part is aliphatic

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Q

State the general formula for alkanes

A

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Q

Give the formula for an alkane containing 5 carbon atoms

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Q

Give the formula for an alkane containing 14 H atoms.

A

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Q

Systematically name the following:

A

2-methylbutane ✓ 2,2-dimethylpropane ✓
2,3,4-trimethylpentane ✓ 2,3,4,4-tetramethylhexane ✓

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Q

Identify the monomer in the sections of the following polymers

A

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Q

Identify the monomer in the sections of the following polymers

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Systematically name the following:

2-methylprop-1-ene. ✓ 3,4,4-trimethylhex-1-ene. ✓ 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?

1. Cyclopentane 2. methylcyclobutane 3. ethylcyclopropane 4. 1,2-dimethylcyclopropane 5. 1,1-dimethylcyclopropane 5. ✓

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. ✓ Larger molecules have 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

The more branches in an isomer molecule, the lower the boiling point ✓ The less points of surface contact with 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 larger and has 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 more points of surface contact between 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 ✓

State two limitations of using free radical substitution to synthesis haloalkanes

Further substitution occurs. ✓ Substitution occurs at a different position along the carbon chain resulting in isomers being formed. ✓

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.

Suggest how you could monitor the rate of hydrolysis of haloalkanes i.e. chloroalkanes, bromoalkanes, iodoalkanes in a rates experiment.

Place each haloalkane into a conical flask above a piece of paper with an X. Add silver nitrate, AgNO3 solution conical flask ✓ Silver ions react with halides as soon as they form and silver halide precipitate formed ✓ Time how long is needed in seconds for precipitate to form. ✓

Haloalkanes react water to form alcohols. State the name of the reaction.

aqueous hydrolysis ✓

Explain the difference in the rate of hydrolysis between 2-iodobutane and 2-chloropropane.

Rate is slower with chloroalkanes ✓ C-I bond is weaker than C-Cl bond ✓

Explain the difference in the rate of hydrolysis between bromocyclobutane and chlorocyclobutane

Rate is slower with chloroalkanes ✓ C-Br bond is weaker than C-Cl bond ✓

Define what is meant by a "nucleophile"

Electron pair donor. ✓

Define what is meant by the use of "curly arrows"

Movement of an electron pair. ✓

Describe how a "π-bond" is formed.

Sideways overlap of p orbitals ✓ to give a π-bond above and below. ✓

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

State and explain the shape around the C atom in a molecule of ethene. Include a bond angle in your answer.

Trigonal planar✓ 120 degrees ✓ There are 4 bonded pairs and 0 lone pairs around the C atom ✓ There are 3 bonding regions/ regions of electron density around the C atom. ✓ All electron pairs repel ✓

Explain the rotation around the C=C bond in a molecule of but-2-ene.

No rotation around C=C bond ✓ as p-orbitals must stay in the same position to overlap and form π-bond ✓

Define what is meant by "stereoisomers".

The same structural formula ✓ But a different arrangement of atoms in space ✓

State and explain the features of a hex-2-ene molecule that lead to E and Z isomers.

Contains a C=C bond which does not rotate and restricts rotation ✓ Each carbon atom of the double bond is attached to two different groups. ✓

What is meant by "E and Z isomers".

(Z) is when both groups are at the ‘same’ side ✓ (E) is when both groups are at ‘either’ side ✓

State the number sigma and pi bonds in butane-1,3-diene.

σ-bonds: 9 ✓ π -bonds: 2 ✓

Explain why ethene is more reactive than ethane.

Ethene contains a π-bond. ✓ π-bonds are weaker than σ-bonds. ✓ π-bonds can break and electrons can be donated to form a bond. ✓

Systematically name the following, including their stereoisomerism.

1. (Z)-but-2-ene ✓ 2. (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 2-chlorobutane 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 cyclohexanol from cyclohexene 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.

Define what is meant by an "electrophile"

Electron pair acceptor ✓

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.

In a reaction between a propene and steam, explain why one organic product is formed in a much greater quantity than the other organic product.

Secondary carbocation is more stable than a primary carbocation ✓ Major product formed from more stable carbocation intermediate ✓ Major product is from a carbocation bonded to more alkyl groups ✓

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.

Define what is meant by a "monomer"

Single repeating unit (normally an alkene in addition polymers) ✓

Define what is meant by a "polymer"

Polymers are made of up of long repeating units of monomers ✓

Explain the difference in reactivity between addition polymers and alkenes

Alkenes are unsaturated compounds ✓ Addition polymers are saturated compounds ✓ Addition polymers are chemically inert and are non-biodegradable ✓

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

Give a property of addition polymers. State an advantage and disadvantage to this property.

Addition polymers are unreactive and so are not biodegradable ✓ Advantage: long lasting and reusable ✓ Disadvantage: difficult to dispose ✓

Suggest when plastic can be placed into landfill.

Too difficult to separate from other waste ✓ Not in sufficient quantities to make separation financially worthwhile ✓ Too difficult technically to recycle ✓

Explain how addition polymers can biodegrade naturally.

UV radiation can cause polymers to photobiodegrade. ✓

Suggest two ways of processing waste polymer other than landfill and recycling.

Use as an organic feedstock ✓ Combustion for energy production ✓

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.

Give the balanced equation for the synthesis of butan-2-ol from 2-chlorobutane.

Give the balanced equation for the synthesis of 2-iodobutane from butan-2-ol.

Give the balanced equation for the synthesis of 1,2,3-tribromopropane from an alcohol.

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

The following compound is reacted with H3PO4 under reflux. Draw the possible organic products formed.

None. ## Footnote OH has no adjacent carbon atoms with a H.

Give the equation for the dehydration of butan-1-ol.

Give the equations for the hydration of but-1-ene to form primary alcohol

Complete the following equation

State one advantage and one disadvantage to burning polymers as a method of disposal.

Combust to generate electricity ✓ CO2 released which is a green house gas causing global warming ✓

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.

Complete the following synthesis map to show the product formed from each reaction. Include

State and explain the shape and bond angle around the oxygen atom in a molecule of ethanol

104.5 degrees ✓ non-linear ✓ There are 2 bonding pairs and 2 lone pairs around the O atom ✓ 4 regions of electron density ✓ All electron pairs repel ✓ Lone pairs repel more than bonding pairs ✓

Explain why propan-1-ol is a liquid at room temperature, but propane is a gas.

Propan-1-ol has hydrogen bonding between molecules ✓ Propane has weak induced dipole-dipole interactions between molecules ✓ Hydrogen bonding is stronger and requires more energy to overcome ✓

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 bonds with water ✓

Explain, with the aid of a diagram, why ethanol is soluble in water. Include relevant dipoles and lone pairs.

Explain why alcohols are good fuels.

They are good fuels with high enthalpies of combustion ✓ Produce a lot of energy per mole of alcohol burnt ✓

Explain why alcohols are added to petrols mixtures

Added to petrol mixtures to prevent incomplete combustion ✓ Contain an internal supply of oxygen in the form of an OH group ✓

Write an equation for the combustion of propan-1-ol.

State and explain the difference in in boiling point between methanol and ethanol.

Ethanol has a longer carbon chain and so more carbon atoms. ✓ Ethanol has more points of surface contact between molecules Ethanol has stronger induced dipole-dipole interactions between molecules ✓ Which requires more energy to overcome. ✓ | If in doubt, draw the structures out and spot the difference

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:

What reagents and contitions are required to oxidise a tertiary alcohol. ✓

None. Tertiary alcohols cannot be oxidised. ✓

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.

For the following reaction: 2-methylbutan-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.

No reaction. ✓

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.

Describe the process of redistillation.

Re-distil to get purer product ✓ Collect the fraction having the boiling point of the pure compound ✓

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.

Describe how IR spectroscopy works.

Beam of infrared radiation is passed through a sample of a chemical ✓ Bonds between different atoms absorb different frequencies of IR radiation ✓ IR radiation causes covalent bonds to vibrate more ✓ IR radiation that is not absorbed is detected by a detector ✓

Give two uses of IR spectroscopy.

Modern breathalysers... Use IR spectroscopy to look for the presence of ethanol in the driver’s breath ✓ Detects O-H bonds ✓ Monitoring gases causing air pollution.... Monitor concentrations of polluting gases in the atmosphere ✓ Examples include CO and NO – Intensity of the peaks corresponding to CO/ NO bonds studied ✓

Give four uses of mass spectrometry

Monitor breathing of patients under anaesthetic ✓ Testing for drug use in athletes/ horses ✓ Analysing molecules in space ✓ Testing for toxic chemicals that may have contaminated marine life ✓

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

State the density of water.

1 g cm-3 ✓