M6S9 – Organic Summary

5

Organic Summary

1 / 10

Free-radical intermediates in the reaction of chlorine with methane include:

(i) CH3.

(ii) H.

(iii) Cl.

(iv) C.

2 / 10

The rate equation for the reaction of hydroxide ions with 2-bromo-2-methylpropane takes the form:

rate = k[C4H9Br].

This indicates that:

(i) the rate determining step involves hydroxide ions

(ii) doubling the concentration of the halogenoalkane doubles the rate of reaction

(iii) the reaction takes place in one step

(iv) the reaction takes place by the SN1 mechanism (a 2 step mechanism)

3 / 10

When ethene reacts with bromine in the presence of aqueous sodium chloride the organic products include:

(i) CH2BrCH2Br

(ii) CH2BrCH2Cl

(iii) CH2ClCH2Br

(iv) CH2ClCH2Cl

4 / 10

Which of these reagents are nucleophiles?

(i) Br2

(ii) NH3

(iii) NO2+

(iv) CN-

5 / 10

Which of these reactions involve heterolytic bond breaking

(i) propene with bromine

(ii) benzene with bromine

(iii) bromobutane with ammonia

(iv) ethane with bromine

6 / 10

The reaction of benzene with ethanoyl chloride in the presence of aluminium chloride

(i) involves CH3-CO+ as an intermediate

(ii) forms C6H5-CO-CH3

(iii) is a substitution reaction

(iv) involves nucleophilic attack on benzene

7 / 10

The nitrating agent for benzene is a mixture of concentrated sulfuric and nitric acids. This mixture produces:

8 / 10

When propene react with hydrogen bromide the main intermediate is:

9 / 10

The relative rates of hydrolysis for these halogenoalkanes are in the order

C4H9I > C4H9Br > C4H9Cl

This trend correlates with the:

10 / 10

NOT ON OCR SPEC. Hint: Esters can be hydrolysed and the initial stage in the mechanism is nucleophilic attack using an oxygen lone pair of the water molecule. RO- is the leaving group and becomes ROH.

18O is a ‘radiolabelled oxygen’.

The reaction of ethyl ethanoate with H218O produces:

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M6S8 – Organic Mechanisms

16

Organic Mechanisms

1 / 10

Which statement helps to explain why propene react with hydrogen bromide to form mainly 2-bromopropane and much less 1-bromopropane?

2 / 10

Which of these chemical species are nucleophiles with react with halogenoalkanes?

(i) cyanide ions

(ii) hydroxide ions

(iii) ammonia molecules

(iv) ammonium ions

3 / 10

Which of these chemical species are electrophiles which add to alkenes?

(i) bromine molecules

(ii) sulfuric acid molecules

(iii) hydrogen bromide molecules

(iv) sulfate ions

4 / 10

In which of these reactions between pairs of reagents is the bond breaking homolytic?

(i) butan-1-ol with sodium bromide and concentrated sulfuric acid

(ii) catalytic cracking of hydrocarbons

(iii) bromine with ethene

(iv) bromine with hexane

5 / 10

In which of these reactions between pairs of reagents is the bond breaking heterolytic?

(i) hydrogen bromide with propene

(ii) hydrogen bromide and butan-1-ol

(iii) sodium hydroxide with 1-bromopropane

(iv) bromine with hexane

6 / 10

Which of these changes represents a termination step of a chain reaction?

(i) CH3. + CH3. -> CH3CH3

(ii) CH3. + Br2 -> CH3Br + Br.

(iii) Br. + Br. -> Br2

(iv) Br. + CH4 -> CH3. + HBr

7 / 10

In which of these organic compounds are all the bonds non-polar?

(i) 1-bromobutane

(ii) butene

(iii) butan-2-ol

(iv) butane

8 / 10

Which of these conversions is an example of nucleophilic substitution?

9 / 10

Which of these statements defines a free radical?

10 / 10

Methane reacts with chlorine in the presence of ultraviolet light. The reactive chemical species which attacks methane molecules during the reaction is:

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M6S7 – Organic Synthesis

35

Organic Synthesis

1 / 10

Step 1:

2 / 10

Step 2:

3 / 10

Step 3:

4 / 10

Step 4:

5 / 10

Step 5:

6 / 10

Step 6:

7 / 10

Step 7:

8 / 10

Step 8:

9 / 10

Step 9:

10 / 10

Step 10:

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M6S6 – Polymers

8

Polymers

1 / 10

Which of these procedures is used on a large scale to recover some value from plastic waste?

(i) burning the plastic in incinerators and using the energy to generate electricity

(ii) re-melting the plastic and spinning the melt into fibres

(iii) heating the waste with catalysts but no air to produce feedstocks for the chemical industry

(iv) washing plastic bottles on high-speed automatic machines so that they can be reused.

2 / 10

Which of these factors can make it hard to recycle polymeric materials from domestic waste:

(i) much plastic waste consists of containers which have a very low density,

(ii) it is hard for householders to distinguish one plastic from another

(iii) the presence of pigments and fillers often contaminates the pure polymers

(iv) polymers are so similar that no automatic methods of separation are practicable.

3 / 10

Mixing poly(chloroethene) with a plasticiser makes is suitable for use as:

(i) window frames

(ii) insulation for electric cables

(iii) water pipes

(iv) waterproof clothing

4 / 10

Which of these characteristics of polymers accounts for the difference between low density and high density poly(ethene)?

[1] the average length of the polymer chains

[2] the type of intermolecular (interchain) forces

[3] the number and size of bulky side groups

[4] the extent of chain branching

5 / 10

Which of these repeat units gives rise to a polymer which is soluble in water:

6 / 10

Which of these polymers would you expect to have the strongest intermolecular (interchain) forces as a result of the presence of polar covalent bonds?

7 / 10

The monomer which polymerises to form a plastic which has a smooth, slippery surface and is used to give cooking utensils a non-stick surface is:

8 / 10

What is the repeat unit in the polymer formed from propene?

9 / 10

Which monomer polymerises to form this polymer?

---CH2CHCl-CH2CHCl-CH2CHCl-CH2CHCl---

10 / 10

The formation of a molecules of polythene from CH2=CH2 involves many thousands of:

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M6S5 – Amino Acids

8

Amino Acids

1 / 10

Which of these molecules does NOT consist of one or more chains of amino acids?

(i) The hormone insulin

(ii) The filaments in muscle fibres

(iii) The enzyme in saliva, amylase

(iv) The genetic material, DNA

2 / 10

If an amino acid is written as RCHNH2CO2H, in which of these amino acids is R a polar group?

(i) HSCH2CHNH2CO2H

(ii) C6H5CH2CHNH2CO2H

(iii) HOCH2CHNH2CO2H

(iv) CH3CHNH2CO2H

3 / 10

Which of these amino acids are chiral?

(i) CH3CHNH2CO2H

(ii) C6H5CH2CHNH2CO2H

(iii) HOCH2CHNH2CO2H

(iv) CH2NH2CO2H

4 / 10

Which of these compounds are solids at room temperature?

(i) propane

(ii) propanoic acid

(iii) propylamine

(iv) 2-aminopropanoic acid

5 / 10

Which of these phrases describes the tertiary structure of a protein?

6 / 10

The main forces which hold a coiled protein chain into an alpha-helix are:

7 / 10

Breaking down a polypeptide into amino acids by heating with dilute hydrochloric acid is an example of:

8 / 10

In a peptide made up of a sequence of four amino acids the number of peptide bonds is:

9 / 10

Glycine reacts with dilute hydrochloric acid to form:

10 / 10

Which of these formulae represent glycine in aqueous solution at pH 9?

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M6S4 – Amines & Amides

12

Amines & Amides

1 / 10

In the synthesis of ethylamine from bromoethane, the reaction is performed at a high pressure with a large excess of ammonia. The principal reason(s) for this include :

(i) increasing the rate of the reaction

(ii) to minimise the chance of diethylamine and triethylamine being produced

(iii) to push the equilibrium to the right, away from the ammonium salt towards the free amine.

(iv) to reduce the activation energy for the process

2 / 10

Examples of polymers that contain the amide bond include:

(i) sugars

(ii) DNA

(iii) TeryleneTM(PET)

(iv) proteins

 

3 / 10

If the paracetamol molecule shown below is hydrolysed in hot dilute hydrochloric acid, what are the main organic products?

4 / 10

If the molecule shown below is hydrolysed in hot sodium hydroxide, what are the main organic products?

5 / 10

Which is the most typical reaction of an amine in organic synthesis?

6 / 10

Which of the following molecules would you predict to be the least nucleophilic?

7 / 10

Which of the following molecules would you predict to be the most basic?

8 / 10

Which of the following molecules would you predict to be the most soluble in water?

9 / 10

Which of the following molecules is/are examples of 2o amines?

(i) 

(ii)

(iii) 

(iv) 

10 / 10

What is the systematic name of the following molecule?

CH3CH2CH2C(NH2)CHCH3

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M6S3 – Arenes

20

Arenes

1 / 10

Which types of change are involved in this sequence of reactions, though not necessarily in the order listed?

CH3CO-C6H5 -> CH3CO-C6H4-NO2 -> CH3CHOH-C6H4-NO2 -> CH3CH(OCOCH3)-C6H4-NO2

(i) esterification

(ii) reduction

(iii) nitration

(iv) hydrolysis

2 / 10

Which of these chemical species are electrophiles that react with the benzene ring

(i) Br+

(ii) Na+

(iii) NO2+

(iv) H3O+

3 / 10

Which of these properties of benzene are associated with the presence of delocalised electrons?

(i) There are no isomers of 1,2-dichlorobenzene

(ii) Benzene is more stable than might otherwise be expected

(iii) Benzene typically undergoes substitution rather than addition reactions

(iv) Benzene reacts with nucleophiles

4 / 10

The reaction mixture must be completely dry during a Friedel-Crafts acylation or alkylation reaction to:

5 / 10

What is the main organic product when benzene reacts with 2-iodo-2-methylpropane in the presence of aluminium chloride?

6 / 10

What is the reagent used to convert benzene to nitrobenzene?

7 / 10

The reaction using a mixture of benzene and ethene in the presence of hydrogen chloride and aluminium chloride produces an important intermediate in the manufacture of:

8 / 10

What is the organic product when benzene reacts with ethanoyl chloride in the presence of aluminium chloride?

9 / 10

Heating methylbenzene under reflux with excess, alkaline potassium manganate(VII) which is a strong oxidising agent produces:

10 / 10

What are the reagents and conditions for converting benzene to bromobenzene?

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M6S2 – Carboxylic Acids & Esters

21

Carboxylic Acids & Esters

1 / 10

The compound CH3(CH2)4CH=CHCH2CH=CH(CH2)6CO2H is:

(i) a fatty acid

(ii) unsaturated

(iii) called octadec-9,12-dienoic acid

(iv) obtained by the hydrolysis of animal fats

2 / 10

During the synthesis of an ester from a carboxylic acid and an alcohol the extent of conversion of the carboxylic acid to its ester at equilibrium increases if:

(i) the alcohol is added in excess

(ii) concentrated sulfuric acid is added

(iii) the ester distills off from the reaction mixture as it forms

(iv) an acid catalyst is added

3 / 10

Which types of change are involved in this sequence of changes (but not necessarily in the order listed)?

CH3CH2CH2OH -> CH3CH2CHO -> CH3CH2CO2H -> CH3CH2CO2CH2CH3

(i) hydrolysis

(ii) esterification

(iii) acid-base

(iv) oxidation

4 / 10

Which of the listed liquids reacts with sodium borohydride NaBH4 in a nucleophilic addition reaction?

(i) CH3CH2OH

(ii)CH3COCH3

(iii)CH3CO2H

(iv)CH3CHO

5 / 10

Ethyl ethanoate is heated under reflux with excess aqueous sodium hydroxide. The resulting solution is distilled. The distillate contains:

6 / 10

What are the products of the acid hydrolysis of methyl propanoate?

7 / 10

The reagent which converts ethanoic acid to ethanoyl chloride is:

8 / 10

Excess LiAlH4 in dry ether (this reacts similarly to NaBH4 but is more reactive), converts propanoic acid to:

9 / 10

The product of the reaction of ethanoic acid and ammonia at room temperature is:

10 / 10

How any moles of aqueous sodium hydroxide react with 2 mol of ethanedioic acid?

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M6S1 – Carbonyls

44

Carbonyls

1 / 10

Which of these compounds are functional group isomers?

(i) CH3CHCHOH

(ii) CH3CH2CHO

(iii) CH3COCH3

(iv) CH3CH2COCH3

2 / 10

The hydride ion, H-, is:

(i) a reducing agent

(ii) a nucleophile

(iii) a base

(iv) a free radical

3 / 10

Reagents which can be used in a test-tube test to distinguish aldehydes from ketones are:

(i) Tollen's reagent

(ii) 2,4-dinitrophenylhydrazine

(iii) Fehling's solution

(iv) sulfuric acid

4 / 10

A compound P, C4H8O, gave on oxidation an acid C4H8O2. Which of the following are possible structures for P?

(i)CH3CH2CH2CHO

(ii)CH3COCH2CH3

(iii) (CH3)2CHCHO

(iv) CH3CH=CHCH2OH

5 / 10

A sample of propan-2-ol was heated under reflux with an acidified, aqueous solution of potassium dichromate(VI). The resulting mixture was then distilled. The distillate contained:

(i) propanoic acid

(ii) propanone

(iii) propanal

(iv) water

 

6 / 10

Which of these aldehydes are isomers of pentan-2-one?

(i) pentanal

(ii) 2-methylbutanal

(iii) 3-methylbutanal

(iv) 2,2-dimethylbutanal

7 / 10

The reaction of propanone with HCN in the presence of some KCN is an example of:

8 / 10

Treating ethanal with hydrogen cyanide in the presence of some KCN and then hydrolysing the product with hot hydrochloric acid (which converts a cyano / nitrile group RCN, to RCOOH) produces:

9 / 10

Which reagent converts butan-2-one to butan-2-ol?

10 / 10

Which types of alcohol, when heated under reflux with acidified potassium dichromate(VI), turn the colour of the solution from orange to green?

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pH Buffer Calculations 3

0

pH Buffer Calculations 3

1 / 10

Calculate the mass of potassium methanoate salt ( Mr of 84.1 ) that would need to be added to 80.0 cm3 of 0.900 mol dm-3 methanoic acid solution to produce a pH of 4.31

The acid dissociation constant, Ka, for methanoic acid is 1.78 x 10-4 mol dm-3

2 / 10

Calculate the mass of potassium methanoate salt ( Mr of 84.1 ) that would need to be added to 90.0 cm3 of 0.100 mol dm-3 methanoic acid solution to produce a pH of 3.83

The acid dissociation constant, Ka, for methanoic acid is 1.78 x 10-4 mol dm-3

3 / 10

Calculate the mass of sodium ethanoate salt ( Mr of 82 ) that would need to be added to 50.0 cm3 of 0.100 mol dm-3 ethanoic acid solution to produce a pH of 5.06

The acid dissociation constant, Ka, for ethanoic acid is 1.70 x 10-5 mol dm-3

4 / 10

Calculate the pH of a solution produced when 0.750 g of sodium ethanoate salt ( Mr of 82 )is added to 50.0 cm3 of 0.100 mol dm-3 ethanoic acid solution.

The acid dissociation constant, Ka, for ethanoic acid is 1.70 x 10-5mol dm-

5 / 10

Calculate the pH of a solution produced when 0.410 g of sodium methanoate salt ( Mr of 68 )is added to 75.0 cm3 of 0.200 mol dm-3 methanoic acid solution.

The acid dissociation constant, Ka, for methanoic acid is 1.78 x 10-4mol dm-3

6 / 10

Calculate the pH of a solution produced when 0.205 g of lithium ethanoate salt ( Mr of 66 )is added to 100.0 cm3 of 0.100 mol dm-3 ethanoic acid solution.

The acid dissociation constant, Ka, for ethanoic acid is 1.70 x 10-5mol dm-3

7 / 10

Calculate the pH of a solution produced when 0.150 g of sodium ethanoate salt ( Mr of 82 )is added to 50.0 cm3 of 0.100 mol dm-3 ethanoic acid solution.

The acid dissociation constant, Ka, for ethanoic acid is 1.70 x 10-5mol dm-3

8 / 10

Calculate the pH of a solution produced when 28.0 cm3 of 0.100 mol dm-3 potassium hydroxide solution has been added to 94.0cm3 of 0.100 mol dm-3 hydrocyanic acid solution.

The acid dissociation constant, Ka, for hydrocyanic acid is 6.20 x 10-10 mol dm-3

9 / 10

Calculate the pH of a solution produced when 35.0 cm3 of 0.280 mol dm-3 sodium hydroxide solution has been added to 75.0cm3 of 0.300 mol dm-3 phenol solution.

The acid dissociation constant, Ka, for phenol is 1.00 x 10-10 mol dm-3

10 / 10

Calculate the mass of lithium fluoride salt ( Mr of 25.9 ) that would need to be added to 50.0 cm3 of 0.500 mol dm-3 hydrofluoric acid solution to produce a pH of 3.00

The acid dissociation constant, Ka, for hydrofluoric acid is 6.60 x 10-4 mol dm-3

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