Exam code: 7405
State whether the following amines can be classed either primary, secondary or tertiary.
i) Ethylamine
ii) 2-aminopropane
iii) Phenylamine
Name the amines shown in Figure 1.
Figure 1
Complete the equation for the formation of ethylamine.
CH3CH2Br + __________ → __________ + NH4Br
State the reagents and conditions required for the conversion of 1-bromopropane into propylamine.
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Chloroethane will react with ethylamine to produce a secondary amine. Complete the reaction mechanism in Figure 1 for the formation of the secondary amine.
Figure 1
Give the name of the mechanism outlined in part (a)
Chloroethane, CH3CH2Cl, can also produce an amine by first heating under reflux with ethanolic potassium cyanide, KCN. The amine can then be formed in the second step from the nitrile produced.
State the conditions required to produce the amine in the second step of this method.
State one disadvantage for the preparation of an amine from a halogenoalkane in one step as opposed to a two step process.
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Write an equation to show how propylamine can act as a base if reacted with hydrochloric acid and give the name of the product formed.
Explain why phenylamine, shown in Figure 1, is a weaker base than ammonia.
Figure 1
Explain why ammonia is a weaker base than methylamine.
Phenylamine can be prepared from nitrobenzene, state the reagents and conditions required for this reaction.
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Quaternary ammonium salts can be made from the reaction of a halogenoalkane such as chloroethane with ammonia. Give a use of a quaternary ammonium salt.
State the name of the quaternary ammonium salt shown in Figure 1.
Figure 1
Give a condition for the reaction between chloroethane and ammonia that would favour the formation of a quaternary ammonium salt.
Outline the reaction mechanism between a molecule of chloroethane and two molecules of ammonia to produce ethylamine.
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Explain why secondary amines are stronger bases than primary amines.
Complete the nucleophilic addition elimination mechanism outlined in Figure 1 to show the formation of an amide from ethanoyl chloride and ammonia and state the name of the final product.
Figure 1
Another amide is produced in a separate reaction, this is shown in Figure 2. State the name of this amide.
Figure 2
Give two disadvantages of using an acid chloride to produce an amide and give an alternative reagent to form an amide from an amine.
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Name the compound drawn in Figure 1 and state the class of compound to which it belongs.
Figure 1
The compound in Figure 1 in part (a) can be formed during the reaction of ethylamine, CH3CH2NH2, and chloroethane, CH3CH2Cl.
Name and outline the mechanism for this reaction.
Explain why an excess of ethylamine, CH3CH2NH2, is required for the formation of the compound in Figure 1 in part (a).
Triethylamine, (CH3CH2)3N and the compound in Figure 1 of part (a) are two different types of amines.
i) Explain how you could differentiate between these two compounds using an IR spectrum.
ii) Triethylamine, (CH3CH2)3N can also undergo a reaction with chloroethane. Draw and give a use for the product of this reaction.
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Amines will react with acid chlorides to produce a different nitrogen containing product.
i) Name and outline the mechanism between ethanoyl chloride, CH3COCl and methylamine, CH3NH2.
ii) Give the IUPAC name of the compound formed in the reaction.
Name and draw the structure of the two compounds formed in the reaction of methylamine, CH3NH2 and propanoic anhydride.
Methylamine, CH3NH2 also reacts with ethanoic anhydride, CH3COOCOCH3 in a less vigorous reaction. Suggest why using an acid anhydride such as ethanoic anhydride is more favourable than using ethanoyl chloride.
i) Two separate solutions of methylamine, CH3NH2 and dimethylamine, (CH3)2NH, were left unlabelled in a laboratory. Suggest how, other than smell, they could be distinguished from one another.
ii) Give an explanation to your answer to part (i).
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Figure 1 shows a reaction scheme in which Compound A undergoes three different reactions to produce three different products.
Figure 1
Explain how the reactions and the conditions of Reaction 2 and Reaction 3 are different from one another.
Compound B drawn in Figure 1 of part (a) is a primary amine.
Give the IUPAC name of Compound B and outline a mechanism for Reaction 1, stating a condition which would reduce contamination of the primary amine.
Draw a branched chain optical isomer of Compound B from Figure 1 that would display optical isomerism.
An alternative method of producing Compound B in Figure 1 part (a) is from 1-bromopropane, CH3CH2CH2Br in two steps.
i) State the reagents and conditions required for both steps of this reaction and give the name of the intermediate compound formed.
ii) Suggest one advantage and one disadvantage for this method.
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The compound drawn in Figure 1 below is caffeine. Caffeine is a stimulant drug that speeds up the messages travelling between the brain and body. Ingesting too much caffeine may promote headaches and high blood pressure.
Figure 1
i) Give the molecular formula of caffeine.
ii) Calculate the percentage by mass of nitrogen in caffeine. Give your answer to 1 decimal
Deduce the total number of peaks in the 13C NMR spectrum of caffeine.
i) Which functional group is not present in a molecule of caffeine drawn in Figure 1 part (a)?
A Alkene
B Ketone
C Amine
D Amide
ii) Give the name, including the classification, of the functional group that contains the Nitrogen atom labelled c.
Suggest why the nitrogen atoms labelled a and b are unlikely to be protonated.
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Compounds A, B, C and D shown in Figure 1 are all nitrogen compounds. State the IUPAC names for compounds A and B.
Figure 1
State which amine is more basic, compound C or D. Explain your answer.
Explain why 2-chloropyridine shown in Figure 2 is less basic than pyridine.
Figure 2
Outline the mechanism for the formation of compound B using the required acyl chloride.
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Phenylamine is a weak base and can be prepared from benzene in two steps. State the reagents and conditions required for the preparation of phenylamine from benzene.
Write an equation to show how the free amine is liberated from the salt formed in the second step using sodium hydroxide.
Explain why phenylamine can not be prepared from chlorobenzene via reaction with ammonia under normal conditions.
Explain why phenylamine is insoluble in water.
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2-bromopropane can undergo a two step process to form a primary amine containing four carbon atoms.
i) State the name of the primary amine produced after both steps.
ii) Give the reagents and conditions required to form the intermediate compound in step one.
In step two the amine is produced from the intermediate formed in step 1.
i) Draw the structure for the intermediate formed in step one.
ii) State the reagents and conditions required for step two.
iii) Write an equation for the reaction that occurs in step two.
If excess 2-bromopropane is used in part (a), further substitution will occur. Outline the mechanism for the formation of the tertiary amine from a secondary amine for the reaction between excess 2-bromopropane and propylamine.
A solid product is produced in the reaction in part (c). Draw the structure of the solid produced in this reaction.
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Compound X is produced from cyclohexene. An amine which is a relatively weak base containing one nitrogen atom can be produced from Compound X in one step.
Outline a mechanism for the formation of Compound X from cyclohexene. You will need to give suitable reagents in your answer.
State the reagents and conditions for the conversion of Compound X into the amine molecule.
Figure 1 shows three amine compounds, Compounds E, F and G.
Figure 1
List the amines in order of increasing basicity. Justify your answer.
Write an equation to show how propylamine will react when mixed with water.
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Methyl orange is an azo dye which exists in two forms depending on the pH.
Figure 1
Suggest a structure for the diazonium salt that is used to form methyl orange which has the formula C6H4(SO3Na)NH2.
Ethylamine will react with propanoic anhydride to produce two compounds, draw the compounds produced in this reaction.
A reaction scheme for the production of a secondary amine, Compound Z, is given in the following sequence shown in Figure 2.
Figure 2
i) Give the reagents and conditions required for Step 1.
ii) Give the IUPAC name for compound Y.
The amine produced, compound Z, is a secondary amine.
i) Propylamine is reacted with chloromethane to produce compound Z. Draw a possible structure for compound Z.
ii) Give one advantage of forming an amine through this method.
iii) Compound Z is reacted with excess chloromethane. Draw the solid product formed from this reaction.
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