CHEM J-8 June Complete the following table. Make sure you give the name of the starting material where indicated. REAGENTS/ CONDITIONS

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1 CHEM J-8 June 2014 Complete the following table. Make sure you give the name of the starting material where indicated. STARTING MATERIAL REAGENTS/ CNDITINS STRUCTURAL FRMULA(S) F MAJR RGANIC PRDUCT(S) 4 Cl (CH 3 ) 2 NH hot 3 M NaH

2 CHEM J-9 June 2014 Methylphenidate, also known as Ritalin, is a psychostimulant drug approved for the treatment of attention-deficit disorder. Identify all stereogenic (chiral) centres in methylphenidate by clearly marking each with an asterisk (*) on the structure below. 7 methylphenidate Using one stereogenic centre you have identified, draw the (R)-configuration of that centre. How many stereoisomers are there of methylphenidate? Describe the relationships between these isomers. Give the products formed when methylphenidate is hydrolysed with 4 M HCl.

3 CHEM J-12 June 2014 Show clearly the reagents you would use to carry out the following chemical conversions. More than one step is required in each case. Give the structure of any intermediate compounds formed. 3

4 CHEM N-8 November 2014 Complete the following table. STARTING MATERIAL REAGENTS/CNDITINS THE MAJR RGANIC PRDUCT(S) 1 SCl 2

5 CHEM N-9 November 2014 Draw the structure of the organic product(s) formed when each of the following compounds is treated with 4 M sodium hydroxide. The first reaction requires heating. 3 Compound rganic products

6 CHEM J-9 June 2013 Complete the following table. STARTING MATERIAL REAGENTS/ CNDITINS CNSTITUTINAL FRMULA(S) F MAJR RGANIC PRDUCT(S) 3

7 CHEM J-14 June 2013 Below is the reaction between an acid chloride and water to give a carboxylic acid. Provide curly arrows for this mechanism and draw the structures of the two intermediates on the pathway. 6 Indicate the hybridisation of the two oxygen atoms in the starting materials. acid chloride: water: THE REMAINDER F THIS PAGE IS FR RUGH WRKING NLY.

8 CHEM N-8 November 2013 Complete the following table. STARTING MATERIAL REAGENTS/ CNDITINS CNSTITUTINAL FRMULA(S) F MAJR RGANIC PRDUCT(S) 1

9 CHEM N-12 November 2013 The polymer Nylon 66 can be made by mixing the following two reagents. 2 Draw the structure of Nylon 66.

10 CHEM N-12 November 2013 Consider the three compounds shown below. 3 Arrange these compounds in order of increasing acidity. Explain your reasoning.

11 CHEM N-13 November 2013 The incomplete mechanism for the reaction of acetyl chloride with hydroxide ions is shown below. The reaction occurs in three steps. In each step complete the mechanism by adding curly arrows to indicate the bond changes taking place. 3

12 CHEM J-9 June 2012 Indicate the hybridisation of the carbon and nitrogen atoms in the diamine P. 4 Draw the product of the reaction when diacyl chloride Q reacts with water. Kevlar (used in bullet-proof vests) is a polyamide polymer which is made from diacyl chloride building block Q and diamine building block P. Draw the repeating polymer unit formed in the reaction of P with Q. THE REMAINDER F THIS PAGE IS FR RUGH WRKING NLY.

13 CHEM J-10 June 2012 Complete the following table. If there is no reaction, write NR. Show any relevant stereochemistry. STARTING MATERIAL REAGENTS/ CNDITINS CNSTITUTINAL FRMULA(S) F MAJR RGANIC PRDUCT(S) 4 Cr / H + H + catalyst / heat (CH 3 ) 2 NH / heat

14 CHEM J-12 June 2012 Consider the following molecule (M) isolated from a natural source. H N CH H 2 N (M) 6 NH 2 Give the products when molecule (M) is hydrolysed by heating it with 6 M HCl. Make sure you show the products in their correct ionisation states.

15 CHEM J-13 June 2012 Compound T is a precursor in the synthesis of the asthma drug salbutamol. 3 Give the molecular formula of compound T. Give the structure(s) of all organic products formed when compound T is heated with 4 M NaH. THE REMAINDER F THIS PAGE IS FR RUGH WRKING NLY.

16 CHEM N-10 November 2012 Complete the following table. STARTING MATERIAL REAGENTS/ CNDITINS CNSTITUTINAL FRMULA(S) F MAJR RGANIC PRDUCT(S) 1

17 CHEM N-11 November 2012 Draw the structure of the organic product(s) formed when each of the following compounds is treated with 4 M sodium hydroxide. The first two reactions proceed at room temperature; the last one requires heating. 4 Compound rganic Product(s) THE REMAINDER F THIS PAGE IS FR RUGH WRKING NLY.

18 CHEM J-11 June 2010 Give the constitutional formula(s) of the major organic product(s) formed in each of the following reactions. 7 Br CCH 3 1. LiAlH 4 2. H / H 2 10 M HCl H 4 M NaH heat N H Me 6 M HCl heat excess CH 3 NH 2

19 CHEM N-9 November 2010 Complete the following table. STARTING MATERIAL REAGENTS/ CNDITINS CNSTITUTINAL FRMULA(S) F MAJR RGANIC PRDUCT(S) 2 H Cl H / H 2 /heat Page Total:

20 CHEM N-10 November 2010 The following is a nucleophilic addition-elimination reaction between ammonia and an acid anhydride. Provide curly arrows needed for the mechanism, and draw the structures of the two intermediates on this pathway. 5 reactants NH 3 intermediate 1 H H 2 N products intermediate 2 THE REMAINDER F THIS PAGE IS FR RUGH WRKING NLY. Page Total:

21 CHEM J-8 22/06(a) Complete the following table. Make sure you indicate any relevant stereochemistry. STARTING MATERIAL REAGENTS/ CNDITINS CNSTITUTINAL FRMULA(S) F MAJR RGANIC PRDUCT(S) 6 H 1. dilute NaH 2. CH 3 Br H Cr / H Br 1. Mg / dry ether 2. H 2 CH 1. NaBH 4 2. H + / H 2

22 CHEM J-9 22/06(a) Give the constitutional formula(s) of the organic product(s) formed when each of the following compounds is treated with 4 M sodium hydroxide. The first three reactions proceed at room temperature; the last two require heating. 7 CMPUND RGANIC PRDUCT(S) CH 3 CH 2 CH CH 3 H CH 3 N CH 3 Br H 3 C CH C H 3 C Cl H3 C C N

23 CHEM N-9 22/08(a) Consider the following reaction sequence. 6 K H Reagent A Reagent B L + M N + HCl A Compound K below can be converted into two different intermediates, L and M, which can react together to give compound N and the inorganic byproduct HCl. Give the reagents A and B and draw the structure of the intermediates L and M. B L M

24 CHEM N-10 22/08(a) Give the constitutional formula(s) of the organic products formed in each of the following reactions 3 NH 2 CH 3 Br NaCN 4 M NaH heat THE REMAINDER F THIS PAGE IS FR RUGH WRKING NLY.

25 CHEM J-8 June /06(a) Complete the following table. Make sure you indicate any relevant stereochemistry. STARTING MATERIAL REAGENTS/ CNDITINS CNSTITUTINAL FRMULA(S) F MAJR RGANIC PRDUCT(S) 4 CH 3 CH 2 CH 1. SCl 2 2. CH 3 CH 2 H CH 3 CH 2 CH 2 CH 2 CH 2 H CH 3 C C CH3 conc. H 2 S 4 catalyst CH 3 C Cl H 2 C H 1. LiAlH 4 / dry ether 2. H / H 2

26 CHEM J-10 June /06(a) The structure of methyl 4-aminobenzoate, (E), is given below. 5 (E) b H 2 N a Give the molecular formula of compound (E). Name the functional groups in molecule (E) indicated by the boxes a and b. a: b: Give the structure(s) of all organic products formed when compound (E) is treated with the following reagents. If no reaction occurs, write N REACTIN. cold HCl (1 M) hot NaH (4 M) hot HCl (4 M)

27 CHEM N-10 November /08(a) The structure of the antihistamine, Zyrtec TM, is given below. 5 N Cl N A B H C What is the name of the functional group in Box A? What is the name of the functional group in Box B? What is the name of the functional group in Box C? By drawing an arrow on the structure above, clearly indicate the stereocentre in the structure of Zyrtec. Draw the product of the reaction when Zyrtec is treated with LiAlH 4 followed by dilute acid.

28 CHEM J-7 June /06(a) Draw the structure of the major organic product formed in the following reactions CH 3 MgBr 2. H / H 2 H CH 3 CH 2 H / H 1. NaBH 4 2. H / H 2

29 CHEM J-8 June /06(a) Suggest reagents you could use to achieve the following transformations. CH 3 A Na 4 B Br C intermediate compound D H A: B: C: D: H / H 2 THE REMAINDER F THIS PAGE IS FR RUGH WRKING NLY.

30 CHEM J-10 June /06(a) The amino acids serine and valine are shown below. H 7 H H 2 N C 2 H H H 2 N C 2 H serine valine List the substituents attached to the stereogenic centre of valine in order of decreasing priority. highest priority lowest priority Assign the absolute configuration of the stereoisomer of valine shown above. Draw a dipeptide formed by the condensation of serine with valine. What are the two key elements of protein secondary structure? THE REMAINDER F THIS PAGE IS FR RUGH WRKING NLY.

31 CHEM N-9 November /08(a) The structure of salbutamol, a drug used to treat bronchospasms, is given below. H H H H N 5 Give the molecular formula of salbutamol. Calculate the m/z value for the major peak you would expect to see for the molecular ion in the high resolution mass spectrum. [Atomic masses: 1 H = ; 12 C = ; 16 = ; 14 N = ] Answer: Give the structure(s) of the major organic products formed when salbutamol is treated with the following reagents. cold HCl (1 M) NaH (1 M) Cr / H

32 CHEM N-10 November /08(a) Complete the following table. Starting material Reagents / Conditions Major organic product(s) 2 C H C Cl H 1. NaBH 4 2. H / H 2 THE REMAINDER F THIS PAGE IS FR RUGH WRKING NLY.

33 CHEM N-11 November 2007 Consider the reaction sequence below. 2 H Cl H Draw the structures of products A and B. A + B A B Draw the structure of the product, C, from the following reaction. 3 C CH 3 excess H 2 Pd/C catalyst Product C undergoes hydrolysis when heated with 4 M NaH. Give the structures of the products (in their correct ionic states) formed in this reaction.

34 CHEM N-12 November /08(a) The incomplete proposed mechanism for the reaction of acetyl chloride with ammonia is shown below. Complete the mechanism by adding curly arrows to illustrate the bonding changes that take place. 5 Cl Cl NH 3 H N H H Cl + NH 2 H Cl N H + H THE REMAINDER F THIS PAGE IS FR RUGH WRKING NLY.

35 CHEM J-7 June 2006 Draw the structure of the major organic product formed in the following reactions. 5 H SCl 2 H H 1. LiAlH 4 2. H / H 2

36 CHEM J-10 June 2006 The amino acid serine is shown below: H 6 H H 2 N CH List the substituents attached to the stereogenic centre in order of decreasing priority. highest priority lowest priority Assign the absolute configuration of the stereoisomer shown above. Draw the dipeptide formed by the condensation of two serine residues. Explain briefly what is meant by the primary structure of a protein. Draw the repeating unit of the polymer formed in the following reaction. 2 Cl Cl + H 2 N NH 2

37 CHEM N-7 November 2006 The structure of lignocaine, a local anaesthetic, is given below. 7 a H N N b Give the molecular formula of lignocaine. Name the functional groups in lignocaine indicated by boxes a and b. a: b: Give the structure(s) of all organic products formed when lignocaine is treated with the following reagents. If no reaction occurs, write N REACTIN. cold HCl (1 M) hot NaH (4 M) hot HCl (4 M)

38 CHEM N-8 November 2006 Draw the constitutional formula of the major organic product formed in each of the following reactions. 6 H SCl 2 H CH 3 CH H / heat H Cr / H CH 1. LiAlH 4 2. H / H 2

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