21. Organic synthesis
A section of Chemistry, 9701
Listing 10 of 83 questions
3-aminobenzoicacid can be synthesised from methylbenzene in three steps. methylbenzene 3-aminobenzoic acid step 1 step 2 step 3 M N CO2H NH2 Draw the structures of M and N in the boxes. Suggest reagents and conditions for each step of the synthesis. step 1 step 2 step 3  A mixture of serine, HOCH2CH(NH2)CO2H, and lysine, H2N(CH2)4CH(NH2)CO2H, reacts to form several different products. Draw the structures of the two structural isomers with the molecular formula C6H12N2O5 that could be present in the product mixture. The functional group formed in each case should be displayed.  Predict the number of different structural isomers with the molecular formula C9H19N3O4 that could be present in the product mixture. molecular formula number of structural isomers formed C9H19N3O4  Glutathione is a naturally occurring compound found in plants. glutathione O O O H NH2 O OH SH HO H N N On the diagram of glutathione, label each chiral centre with an asterisk (*). Draw the structures of the three products formed after complete acid hydrolysis of glutathione. Assume the thiol group, –SH, does not react.  Glutathione is soluble in water. By referring to the structure of glutathione, explain why glutathione is soluble in water. 
9701_s21_qp_41
THEORY
2021
Paper 4, Variant 1
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Describe and explain the relative basicities of phenylamine, ethylamine and 4-nitrophenylamine. > > most basic least basic The dye R can be synthesised from 4-nitrophenylamine in two steps. O2N O2N OH N N NH2 4-nitrophenylamine step 1 step 2 Q R Deduce and draw the structure of the organic salt Q in the box. Suggest reagents and conditions for step 1 and 2 in . step 1 step 2  Compound G can be synthesised from methylbenzene in three steps. E step 1 F G step 2 step 3 CH3 CO2H NO2 Br Give the systematic name of compound G. Deduce the identities of E and F and draw their structures in the boxes. Suggest reagents and conditions for each of steps 1 to 3 in . step 1 step 2 step 3  
9701_s21_qp_42
THEORY
2021
Paper 4, Variant 2
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3-aminobenzoicacid can be synthesised from methylbenzene in three steps. methylbenzene 3-aminobenzoic acid step 1 step 2 step 3 M N CO2H NH2 Draw the structures of M and N in the boxes. Suggest reagents and conditions for each step of the synthesis. step 1 step 2 step 3  A mixture of serine, HOCH2CH(NH2)CO2H, and lysine, H2N(CH2)4CH(NH2)CO2H, reacts to form several different products. Draw the structures of the two structural isomers with the molecular formula C6H12N2O5 that could be present in the product mixture. The functional group formed in each case should be displayed.  Predict the number of different structural isomers with the molecular formula C9H19N3O4 that could be present in the product mixture. molecular formula number of structural isomers formed C9H19N3O4  Glutathione is a naturally occurring compound found in plants. glutathione O O O H NH2 O OH SH HO H N N On the diagram of glutathione, label each chiral centre with an asterisk (*). Draw the structures of the three products formed after complete acid hydrolysis of glutathione. Assume the thiol group, –SH, does not react.  Glutathione is soluble in water. By referring to the structure of glutathione, explain why glutathione is soluble in water. 
9701_s21_qp_43
THEORY
2021
Paper 4, Variant 3
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Neotame is an artificial sweetener added to some foods. N N H H O neotame O O O OH State the number of chiral carbon atoms in a molecule of neotame. Neotame contains the arene functional group. Identify all the other functional groups present in neotame. Neotame reacts with an excess of hot NaOHto form three organic products. State the two types of reaction that occur when neotame reacts with hot NaOH. N N H H O neotame O O O OH Draw the structures of the three organic products formed from the reaction of neotame with an excess of hot NaOH.
9701_s24_qp_41
THEORY
2024
Paper 4, Variant 1
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Methyl red can be synthesised as shown in . COOH step 1 P Q NO2 step 2 step 3 methyl red R S COOH N N N Give the systematic name of P. P can be synthesised as shown in . CH3 P NO2 COOH NO2 Suggest reagents and conditions for this reaction. A student attempts to synthesise P by an alternative route, as shown in . Compound T is the major product in this reaction rather than P. COOH T conc. HNO3 conc. H2SO4 COOH NO2 Explain why T is the major product in this reaction. S reacts in a similar way to phenol in step 3. Draw the structures of Q, R and S in the boxes in . Suggest reagents and conditions for steps 1 and 2 in . step 1 step 2 [T t l 9] , ,
9701_s24_qp_42
THEORY
2024
Paper 4, Variant 2
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Neotame is an artificial sweetener added to some foods. N N H H O neotame O O O OH State the number of chiral carbon atoms in a molecule of neotame. Neotame contains the arene functional group. Identify all the other functional groups present in neotame. Neotame reacts with an excess of hot NaOHto form three organic products. State the two types of reaction that occur when neotame reacts with hot NaOH. N N H H O neotame O O O OH Draw the structures of the three organic products formed from the reaction of neotame with an excess of hot NaOH.
9701_s24_qp_43
THEORY
2024
Paper 4, Variant 3
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Use 4-Amino-1-methylbenzene, F, is a useful starting material for making several dyes. The following chart shows some of its reactions. Suggest reagents and conditions for reaction I. Draw the structural formulae of compounds G and H in the boxes above. Name the functional group you have drawn in compound G. CH3 CH3 NH2 Br Br NH2 + CH3COCl + HCl reaction II reaction I reaction III H G F The dye J can be made from F by the following series of reactions. Suggest reagents and conditions for reaction IV, reaction V. Many dyestuffs used as food colourings, such as Sunset Yellow, contain sodium sulphonate (–SO3 –Na+) groups attached to the rings. Suggest, with an explanation, a reason for this. N N SO 3 Na+ Sunset Yellow SO 3 Na+ HO – – H3C NH2 reaction IV reaction V H3C N2Cl H3C H3C CH3 N N OH F J
9701_w06_qp_4
THEORY
2006
Paper 4, Variant 0
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Compound G can be synthesised from benzene by the route shown below. H J (C6H5N2Cl) G HNO3 + H2SO4 NH2 step 2 step 4 step 5 step 3 55 °C OH O O CH3 Name the functional group formed in step 5. Draw the structures of the intermediates H and J in the boxes above. Suggest reagents and conditions for the following. step 2 step 3 step 4 step 5 In a reaction discovered just over 100 years ago by the German chemist Karl Fries, compound G is converted into compound K when it is heated with AlCl3. Compound K is a structural isomer of G. K (C8H8O2) G AlCl3 O O CH3 Compound K is a 1,4-disubstituted benzene derivative. It is insoluble in water, but dissolves in NaOH. It gives a white precipitate with Br2, and a yellow precipitate with alkaline aqueous iodine. What is meant by the term structural isomerism? Use the information given above to name two functional groups in compound K. Suggest the structural formula of K, and draw it in the box above. Suggest structures for the aromatic products of the following reactions. Br2 NaOH I2 + NaOH K
9701_w10_qp_41
THEORY
2010
Paper 4, Variant 1
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Compound G can be synthesised from benzene by the route shown below. H J (C6H5N2Cl) G HNO3 + H2SO4 NH2 step 2 step 4 step 5 step 3 55 °C OH O O CH3 Name the functional group formed in step 5. Draw the structures of the intermediates H and J in the boxes above. Suggest reagents and conditions for the following. step 2 step 3 step 4 step 5 In a reaction discovered just over 100 years ago by the German chemist Karl Fries, compound G is converted into compound K when it is heated with AlCl3. Compound K is a structural isomer of G. K (C8H8O2) G AlCl3 O O CH3 Compound K is a 1,4-disubstituted benzene derivative. It is insoluble in water, but dissolves in NaOH. It gives a white precipitate with Br2, and a yellow precipitate with alkaline aqueous iodine. What is meant by the term structural isomerism? Use the information given above to name two functional groups in compound K. Suggest the structural formula of K, and draw it in the box above. Suggest structures for the aromatic products of the following reactions. Br2 NaOH I2 + NaOH K
9701_w10_qp_42
THEORY
2010
Paper 4, Variant 2
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Questions Discovered
83