13.1. Formulas, functional groups and the naming of organic compounds
A subsection of Chemistry, 9701, through 13. An introduction to AS Level organic chemistry
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Organic compounds can be distinguished using chemical tests and analytical techniques. Table3.1 shows four pairs of organic compounds. Table 3.1 organic compounds reagent positive result of chemical test on identified compound A1 O H O A2 O B1 O B2 O C1 O O C2 D1 D2 OH CH3 OH Complete Table3.1 to: ● identify a reagent which can distinguish between the compounds in each pair ● give the positive result of the chemical test and identify which compound shows this result. Use a different reagent for each test. A1 and A2 are structural isomers. Define structural isomers. Give the systematic name of B2. Deduce the molecular formula of D1. D2 forms polymerZ when heated gently. Identify the type of polymer that forms from D2. Draw one repeat unit of polymerZ.  Organic compoundE contains three carbon atoms. E reacts with cold dilute acidified KMnO4to form a single compoundF with Mr = 154.9. Fig.3.1 shows the infrared spectrum of E. Fig.3.2 shows the infrared spectrum of F. E transmittance / % wavenumber / cm–1 F transmittance / % wavenumber / cm–1 Table 3.2 bond functional group containing the bond characteristic infrared absorption range (in wavenumbers) / cm–1 C–O hydroxy, ester 1040–1300 C=C aromatic compound, alkene 1500–1680 C=O amide carbonyl, carboxyl ester 1640–1690 1670–1740 1710–1750 C≡N nitrile 2200–2250 C–H alkane 2850–3100 N–H amine, amide 3300–3500 O–H carboxyl hydroxy 2500–3000 3200–3650 Both spectra show absorptions between 2850 and 2950 cm–1 owing to C–H bonds in each molecule. Use the two infrared spectra and Table 3.2 to identify the functional group present only in E. Explain your answer, referring only to absorptions at frequencies greater than 1500 cm–1. functional group explanation  Use the infrared spectrum of F to identify the functional group formed when E reacts with cold dilute acidified KMnO4. Explain your answer, referring only to absorptions at frequencies greater than 1500 cm–1. functional group explanation  The mass spectrum of E shows a molecular ion peak and an M+2 peak of approximately equal abundance at m/e = 120 and 122. Deduce the relative molecular mass, Mr, of E.  Mr = Use the information in 3to suggest a structure for E.  Complete the equation for the reaction of E with cold dilute acidified KMnO4to form F. In the equation, represents cold dilute acidified KMnO4. H2O + + →  C2 can be synthesised using A1 as a single organic reactant. A1 O H O O C2 Devise a multi-step synthetic route to form C2 from A1. Identify relevant reagents and conditions, and state the organic products of each step. 
9701_w22_qp_22
THEORY
2022
Paper 2, Variant 2
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