Describe how an azo dye can be made from phenylamine. Show the structure of the azo dye and the organic intermediate in your answer

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1 1. oloured organic compounds also include azo dyes. Describe how an azo dye can be made from phenylamine. Show the structure of the azo dye and the organic intermediate in your answer [Total 6 marks]. A dye can be made from 4-methylphenylamine and,6-dimethylphenol, shown below. O 3 N methylphenylamine,6-dimethylphenol 4-Methylphenylamine is dissolved in ice-cold hydrochloric acid and sodium nitrite is added. This mixture is then slowly added to an alkaline solution of the phenol to form the dye. (i) Identify the inorganic nitrogen-containing compound formed by the mixture of hydrochloric acid and sodium nitrite.

2 (ii) Draw the structure of the organic compound formed in the ice-cold acidic mixture, showing a displayed formula of the nitrogen-containing group. (iii) State the name of the type of organic compound drawn in (ii). (iv) Suggest why the mixture must be kept at a low temperature. (v) Suggest the structure of the dye. [Total 6 marks]

3 3. 1,4-Diaminobenzene is used in the manufacture of a variety of materials including dyes and polymers. N N 1,4-diaminobenzene (a) Explain what is meant by the term 1,4-diamino in the name of this compound. (b) 1,4-diaminobenzene can be manufactured from 1,4-dinitrobenzene. O N NO N N 1,4-dinitrobenzene 1,4-diaminobenzene (i) What type of reaction is this? (ii) State reagents and conditions that could be used to carry out this reaction.

4 (iii) omplete and balance the equation below for this reaction. ON NO + [] N N + (c) 1,4-Diaminobenzene is used to make permanent black dye for hair. 1,4-Diaminobenzene can irritate the skin because it is basic. Therefore, it is sometimes neutralised with excess hydrochloric acid to give the salt. (i) Explain how the amino groups in a primary amine such as 1,4-diaminobenzene allow the molecule to act as a base. (ii) Draw the structure of the salt formed in this reaction.

5 (iii) State whether you would expect hexane-1,6-diamine to be a stronger or weaker base than 1,4-diaminobenzene. Explain your reasoning. N N hexane-1,6-diamine [3] [Total 14 marks] 4. The method below can be used to make phenylamine from nitrobenzene in the laboratory g of nitrobenzene and 8 g of tin (an excess) were placed into a flask. The flask was fitted with a reflux condenser. oncentrated hydrochloric acid was then added dropwise to the flask. The mixture was heated for 30 minutes to complete the reaction. Once the mixture had cooled, concentrated sodium hydroxide solution was added until the mixture was alkaline. Purification gave a 7.1% yield of phenylamine. (a) Reaction of nitrobenzene with the tin and hydrochloric acid produces phenylammonium chloride as the organic product. (i) omplete the equation for this reaction. NO + [] + l N 3 + l + phenylammonium chloride

6 (ii) State what the symbol [] in the equation represents. (b) When the sodium hydroxide was added, the phenylammonium chloride was converted to phenylamine. Write an equation for this reaction. (c) alculate the mass of phenylamine that was produced from the 3.69 g of nitrobenzene in this experiment. Give your answer to three significant figures. M r : nitrobenzene,13; phenylamine, 93.1 mass of phenylamine =. g [4] [Total 9 marks]

7 5. Amino acids can act as monomers in the formation of polypeptides and proteins. The structures below show three amino acids, glycine, phenylalanine and proline. N OO N OO N OO glycine 6 5 phenylalanine proline Glycine, phenylalanine and proline can react together to form a mixture of tripeptides. (i) Draw the structure of the tripeptide formed in the order glycine, phenylalanine and proline. [3] (ii) ow many different tripetides could have been formed containing glycine, phenylalanine and proline?

8 (iii) The mixture of tripeptides can be analysed by using gas chromatography, coupled with mass spectrometry. Summarise how each method contributes to the analysis. [3] [Total 7 marks]

9 6. The four amino acids shown below are found in proteins and enzymes. N OO N OO N OO ( ) N 4 S glycine lysine cysteine N OO OO glutamic acid Write down the structural formula for a dipeptide formed from one molecule of glycine and one of lysine. [Total marks] 7. ompound A, shown below, is an amino acid that is being used in the development of a new anti-inflammatory drug. O N 3 O compound A

10 (a) (i) Explain why this molecule is described as an amino acid. (ii) State the general formula of an -amino acid. Explain whether or not compound A fits this general formula. (b) ompound A exists as a zwitterion in aqueous solution. (i) Draw the structure of this zwitterion.

11 (ii) Show how the structure of the zwitterion would change if the solution was acidified with dilute hydrochloric acid. (c) The anti-inflammatory drug is made by combining compound A with compound B, shown below. R represents a side chain. O R O compound B Show the structure of the anti-inflammatory drug formed from compound A and compound B. [Total 7 marks]

12 8. In this question, one mark is available for the quality of the use and organisation of scientific terms. In all living organisms a large variety of polypeptides and proteins are formed naturally from -amino acids. State the general formula of an α-amino acid and use it to describe how amino acids can be combined to give a variety of polypeptides and proteins [6] Quality of Written ommunication [Total 7 marks]

13 9. ompound A is currently being tested as a possible anti-allergic drug. O O O N N N O O O compound A ompound A can be hydrolysed to form three organic products. (i) Name a suitable reagent and conditions for the hydrolysis of compound A. (ii) The three organic products all belong to the same class of compound. State the general name for this class of organic compound. (iii) Draw the structure of one of the organic products from the hydrolysis of A using the reagent you have given in (a)(i) above.

14 (iv) Explain what is meant by the term hydrolysis. Use this reaction to illustrate your answer. [Total 7 marks] 10. Glutamic acid and glycine are both -amino acids that occur widely in living organisms. Their structures are shown below. N OO N OO OO glutamic acid glycine (a) (i) State the general formula for an -amino acid.

15 (ii) Explain how glutamic acid and glycine both fit the general formula given in part (i) (b) Amino acids react with both acids and alkalis. Draw structures below to show how the glutamic acid molecule is changed in the presence of excess acid and alkali. N OO excess l(aq) OO glutamic acid excess NaO(aq) [5]

16 (c) In this question, one mark is available for the quality of use and organisation of scientific terms. Glutamic acid exists as two optical isomers, but glycine does not. Explain what structural feature causes optical isomerism in organic molecules. Include appropriate diagrams and use these two amino acids to illustrate your answer. [7] Quality of Written ommunication [Total 16 marks]

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