Question 1a:
Morphine is a naturally occurring opiate found in opium from poppies. Heroin is a synthetic opiate that can be synthesised from morphine. Fig. 1.1 shows the chemical structure of morphine and heroin.
What functional groups are found in morphine?
Question 1b:
Identify the functional group(s) present in heroin, but not in morphine.
Question 1c:
State the reagents and conditions needed to turn morphine into heroin.
Question 1d:
Predict and explain what you would see if morphine and heroin were separately reacted with warm acidified potassium dichromate solution.
Observation ..................................................................................
Explanation ................................................................................................
................................................................................................
Question 2a:
This question is about farnesol, a chemical found in essential oils and used in perfumes, especially in lilac perfumes. The structure of farnesol is shown in Fig. 2.1
Identify two different functional groups found in farnesol and identify their locations in Fig. 2.1.
Question 2b:
Describe how you would expect farnesol to react if shaken with a little bromine water.
Question 2c:
Farnesol is an important starting compound in organic synthesis. Fig. 2.2 shows a two-step synthesis of a compound made from farnesol.
Suggest a new functional group present in the product of the first step.
Question 2d:
Suggest a functional group present in the final product, but not in farnesol.
Question 3a:
The four step synthesis to form propan-1-ol from a ketone is outlined in Fig. 3.1.
i) Name a possible halogenoalkane, D, that undergoes nucleophilic substitution in step to form propan-1-ol.
[1]
ii) Give the reagents and conditions for step 4.
[2]
Question 3b:
Deduce the identity of the alkene, C, in Fig. 3.1 in part (a).
Question 3c:
Suggest why the electrophilic addition reaction in step 3, in Fig. 3.1 in part (a), might not be favourable in an industrial multistep reaction. You should not include economic considerations.
Question 4a:
Benzene and its derivatives are used in various industrial applications, including the production of plastics, synthetic fibres, rubber, dyes, and detergents.
Fig. 4.1 shows three compounds, A, B and C, which are all derivatives of benzene.
Give the systematic names of compounds A, B and C.
Compound A ..................................................
Compound B ..................................................
Compound C ..................................................
Question 4b:
Different functional groups attached to the benzene ring activate specific carbons within the ring structure and make them more likely to react.
State the positions that are activated for the following compounds in part (a).
Compound A ..............................
Compound B ..............................
Question 4c:
Compounds A and B can be synthesised from benzene by the routes shown in Fig. 4.2.
i) Suggest the reagents for steps 1 - 4.
step 1 ................................................................................
step 2 ................................................................................
step 3 ................................................................................
step 4 ................................................................................
[4]
ii) Draw the structures of compounds D and E in the boxes.
[2]
Question 4d:
The route shown in Fig. 4.3 is proposed for the synthesis of compound C.
i) Suggest one set of reagents and conditions that could be used for both steps.
reagents ............................................................
conditions ............................................................
[2]
ii) Suggest why step 2 is less likely to occur.
[1]
Question 5a:
1-(3-aminophenyl)ethanol can be synthesised from benzene by the route shown in Fig. 5.1.
Step 1 involves a reaction with concentrated nitric acid and concentrated sulfuric acid.
i) Name compound A and state the reaction conditions for step 1.
compound A ................................................................................
reaction conditions ................................................................................
[2]
ii) Name the mechanism for the conversion of benzene into compound A and identify the specific species that reacts with benzene.
mechanism ................................................................................
species ................................................................................
[2]
Question 5b:
Step 2, in Fig. 5.1 in part (a), is the reaction of compound A with ethanoyl chloride, CH3COCl, in the presence of a suitable catalyst.
Identify the catalyst required for this reaction and write an equation to show how the catalyst forms the electrophile for this reaction.
Question 5c:
Step 3, in Fig. 5.1 in part (a), is the reaction of compound B with tin and hydrochloric acid, converting a nitro group into an amino group.
State two changes that occur to compound B during this reaction to show that reduction has taken place.
Question 5d:
Step 4, in Fig. 5.1 in part (a), is the reduction of compound C to 1-(3-aminophenyl)ethanol using NaBH4.
The structure of 1-(3-aminophenyl)ethanol is repeated in Fig. 5.2.
i) Draw a circle around the aliphatic functional group that is formed after the reaction of compound C with NaBH4.
[1]
ii) Draw the structure of compound C.
[1]
Question 1a:
Ibuprofen and paracetamol are pain-relief drugs.
Fig. 1.1 Ibuprofen and paracetamol both contain the aryl (benzene) functional group.
Name the other functional groups present in each molecule.
ibuprofen .........................................................................
paracetamol ...................................................................
Question 1b:
Ibuprofen contains a chiral centre and has two enantiomers.
i) State one similarity and one difference in the physical or chemical properties between the two enantiomers.
similarity.......................................
difference.....................................
[1]
ii) Explain what is meant by racemic mixture.
[1]
Question 1c:
Paracetamol reacts separately with the two reagents shown in the table. Complete Table 1.1 by:
• drawing the structures of the organic products formed,
• stating the types of reaction.
Question 1d:
One of the steps in the manufacture of ibuprofen is shown in Fig. 1.2.
i) Write an equation to show how AlCl3 generates the electrophile for the conversion of X into Y.
[1]
ii) Draw the mechanism for the conversion of X into Y. Include all necessary curly arrows and charges.
[3]
iii) Write an equation to show how the AlCl3 is regenerated.
[1]
Question 2a:
Cuminyl alcohol can be synthesised from benzene by the following route shown in Fig. 2.1.
Suggest reagents and conditions for steps 1–4.
step 1 ...................................................
step 2 ...................................................
step 3 ...................................................
step 4 ...................................................
Question 2b:
Name the mechanism of step 2 and state the type of reaction in step 4.
Mechanism of step 2 ..........................................................................................................
Type of reaction in step 4 ....................................................................................................
Question 2c:
Draw the reaction mechanism for step 2.
Question 2d:
Deduce the number of peaks that would be present in the 13C NMR spectrum of cuminyl alcohol.
Question 3a:
Outline how ethanal can be synthesised from ethane in three steps.
State the reaction conditions and reagents and name the type of reaction taking place.
i) Step 1
Reagents ..........................................................................................................
Conditions ..........................................................................................................
Reaction type ..........................................................................................................
[3]
ii) Step 2
Reagents ..........................................................................................................
Conditions ..........................................................................................................
Reaction type ..........................................................................................................
[3]
iii) Step 3
Reagents ..........................................................................................................
Conditions ..........................................................................................................
Reaction type ..........................................................................................................
[3]
Question 3b:
The following reaction pathway in Fig. 3.1 used to produce compounds A and B, which when reacted together, form a branched ester molecule, compound C.
Suggest suitable reagents and conditions for the synthesis of compound A via step 1 and give the name for this type of reaction.
Question 3c:
The ketone in part (a), must be converted to compound B to produce the ester.
i) Name the molecule that is produced from step 2
[1]
ii) Name of the type of reaction that is involved in step 2 and suggest suitable reagents and conditions for this step.
[2]
Question 3d:
Draw the skeletal formula of the ester formed from the reaction scheme.
Question 4a:
Noradrenaline shown in Fig. 4.1 is a hormone and neurotransmitter, which is released during stress to stimulate the heart and increase blood pressure.
State the names of three functional groups in the noradrenaline molecule.
Question 4b:
Consider the following two step synthesis of noradrenaline from dihydroxybenzaldehyde in Fig. 4.2.
Draw the structure of the intermediate Z in the box.
Suggest reagents for steps 1 and 2.
step 1 ..................................................................................................................................
step 2 ..................................................................................................................................
Question 4c:
Dihydroxybenzaldehyde reacts with Br2 (aq).
Describe what you would see during this reaction.
Draw the structure of the product.
Question 5a:
Compound G is a naturally occurring aromatic compound that is present in raspberries.
Identify the functional groups present in compound G.
Question 5b:
Complete Table 5.1 with information about the reactions of the three stated reagents with compound G.
Question 5c:
The dye H can be made from compound G by the route shown below in Fig. 5.1.
i) Draw the structures of the amine J and the intermediate K in the boxes above.
[2]
ii) Suggest reagents and conditions for
step 1 ........................................................................................................................
step 2 ........................................................................................................................
[3]
Question 5d:
Explain why dye H is very stable.
Question 1a:
Benzocaine is an ester-based compound that is used medicinally as a local anaesthetic in pain relievers and cough drops. One of the first industrial processes to manufacture benzocaine was the five-step reaction shown in Fig. 1.1.
Give the systematic name of benzocaine.
Question 1b:
Step 1 involves the reaction of benzene with bromomethane.
i) State a suitable catalyst for step 1.
[1]
ii) Draw a mechanism for step 1. Include all necessary curly arrows, charges and the structure of A.
[3]
Question 1c:
Concentrated sulphuric acid and concentrated nitric acid are used to form the ion required for step 2.
The following equilibrium is the first step in the formation of the ion:
H2SO4 + HNO3 ⇋ HSO4– + H2NO3+
i) State the roles of each acid in this reaction.
[2]
ii) Use your answer to part (i) to suggest the relative strengths of the acids.
[1]
iii) Different isomers with the molecular formula C7H7NO2 can be formed during step 2.
Draw the structure of the isomer B. Explain your answer.
[2]
Question 1d:
Suggest reagents and conditions for steps 3 - 5 of the synthesis.
step 3 ................................................................................
step 4 ................................................................................
step 5 ................................................................................
Question 1e:
Fig. 1.2 shows an alternative reaction scheme for the production of benzocaine.
i) Suggest why this reaction scheme is an improvement.
[1]
ii) Suggest why this reaction scheme may not work.
[1]
Question 2a:
Propanone can be synthesised from 2-bromopropane according to the reaction scheme shown in Fig. 2.1.
Step 1 is not completed in acidic conditions.
Suggest reagents and conditions for each of steps 1 to 3.
step 1 ................................................................................
step 2 ................................................................................
step 3 ................................................................................
Question 2b:
Suggest one reaction, including reagents and conditions, to replace steps 1 and 2.
Question 2c:
Using structural formulae, write an equation for the reaction of compound B with an oxidising agent, [O], to form propanone.
Question 3a:
Ethene is used in the radical-free synthesis of 1-aminopropane as shown.
ethene compound A compound B propylamine
Identify which step of the reaction scheme could use hydrogen cyanide. Explain your answer.
Question 3b:
Draw the skeletal structure of compound A and state the reagents required for its formation.
Question 3c:
The final step of the reaction scheme forms 1-aminopropane from compound B.
Name compound B and identify the type of reaction that compound B undergoes to form propylamine. Explain your answer.
Question 4a:
Sudan II is an azo dye that was used as a colourant in chilli powder until it was banned due to its links to an increased risk of cancer. It can be synthesised from 1,3-dimethylbenzene by the route shown in Fig. 4.1
Draw the structures of the organic compounds A, B, C and D in the boxes.
Question 4b:
i) Write an equation to show the formation of an appropriate reactive species to react with 1,3-dimethylbenzene to form compound A.
[1]
ii) Draw the mechanism for this reaction. Include all necessary curly arrows and charges.
[2]
Question 4c:
Two other structural isomers of compound A could have been formed from the mononitration of 1,3-dimethylbenzene, as shown in Fig. 4.2.
Suggest, with the aid of suitable diagrams, why 1,3-dimethyl-2-nitrobenzene is likely to be the more abundant product.
