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 CEM J-8 June 2014 Complete the following table. Make sure you give the name of the starting material where indicated. STARTIG MATERIAL REAGETS/ CDITIS STRUCTURAL FRMULA(S) F MAJR RGAIC PRDUCT(S) 4 Cl (C 3 ) 2 hot 3 M a

2 CEM 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. ow many stereoisomers are there of methylphenidate? Describe the relationships between these isomers. 4 isomers: there are 2 pairs of enantiomers: Each isomer has 1 enantiomer and 2 diastereoisomers Give the products formed when methylphenidate is hydrolysed with 4 M Cl.

3 CEM 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 CEM ovember 2014 Complete the following table. STARTIG MATERIAL REAGETS/CDITIS TE MAJR RGAIC PRDUCT(S) 1 SCl 2 Cl

5 CEM ovember 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 2

6 CEM J-9 June 2013 Complete the following table. STARTIG MATERIAL REAGETS/ CDITIS CSTITUTIAL FRMULA(S) F MAJR RGAIC PRDUCT(S) 3 SCl 2 C 3 2

7 CEM 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: sp 2 water: sp 3 TE REMAIDER F TIS PAGE IS FR RUG WRKIG LY.

8 CEM ovember 2013 Complete the following table. STARTIG MATERIAL REAGETS/ CDITIS CSTITUTIAL FRMULA(S) F MAJR RGAIC PRDUCT(S) 1 SCl 2

9 CEM ovember 2013 The polymer ylon 66 can be made by mixing the following two reagents. 2 Draw the structure of ylon 66.

10 CEM ovember 2013 Consider the three compounds shown below. 3 Arrange these compounds in order of increasing acidity. Explain your reasoning. Ethanol is the weakest acid as its conjugate base is not resonance stabilised. Phenol is a stronger acid as its conjugate base is resonance stabilised the negative charge can be delocalised into the aromatic ring as shown below. There is even greater resonance stabilisation for the acetate ion (the conjugate base of acetic acid), as the negative charge is delocalised onto the electronegative oxygen atoms (as opposed to the carbon atoms in the case of phenol).

11 CEM ovember 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 CEM 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. TE REMAIDER F TIS PAGE IS FR RUG WRKIG LY.

13 CEM J-10 June 2012 Complete the following table. If there is no reaction, write R. Show any relevant stereochemistry. STARTIG MATERIAL REAGETS/ CDITIS CSTITUTIAL FRMULA(S) F MAJR RGAIC PRDUCT(S) 7 Cr / + + catalyst / heat (C 3 ) 2 / heat

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

15 CEM 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. C Give the structure(s) of all organic products formed when compound T is heated with 4 M a. TE REMAIDER F TIS PAGE IS FR RUG WRKIG LY.

16 CEM ovember 2012 Complete the following table. STARTIG MATERIAL REAGETS/ CDITIS CSTITUTIAL FRMULA(S) F MAJR RGAIC PRDUCT(S) 1 SCl 2

17 CEM ovember 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) TE REMAIDER F TIS PAGE IS FR RUG WRKIG LY.

18 CEM J-11 June 2010 Give the constitutional formula(s) of the major organic product(s) formed in each of the following reactions. 7 Br CC 3 1. LiAl 4 2. / 2 10 M Cl 4 M a heat Me 6 M Cl heat excess C 3 2

19 CEM ovember 2010 Complete the following table. STARTIG MATERIAL REAGETS/ CDITIS CSTITUTIAL FRMULA(S) F MAJR RGAIC PRDUCT(S) 2 SCl 2 Cl / 2 /heat

20 CEM ovember 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

21 CEM J-8 June 2009 Complete the following table. Make sure you indicate any relevant stereochemistry. STARTIG MATERIAL REAGETS/ CDITIS 1. dilute a 2. C 3 Br CSTITUTIAL FRMULA(S) F MAJR RGAIC PRDUCT(S) 4 Cr / Br 1. Mg / dry ether 2. 2 C 1. ab / 2 C The final product may react further: C w hic h m ig ht unde r go int ramolecular es te rif ic ation t o g ive t he c yclic es t e r

22 CEM J-9 June 2009 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 CMPUD C 3 C 2 C RGAIC PRDUCT(S) C 3 C 2 C 2 C 3 C 3 3 C C 3 C 3 Br C 3 3 C C C 3 C Cl 3 C C C 3 C a 3 C C 3 C C a + a a +

23 CEM J-9 June 2009

24 CEM ovember 2009 Consider the following reaction sequence. 6 K Reagent A Reagent B L + M + Cl A Compound K below can be converted into two different intermediates, L and M, which can react together to give compound and the inorganic byproduct Cl. Give the reagents A and B and draw the structure of the intermediates L and M. B SCl 2 1. LiAl 4 / dry ether 2. + / 2 L Cl M

25 CEM ovember 2009 Give the constitutional formula(s) of the organic products formed in each of the following reactions 3 C C 3 Br ac C 4 M a heat +

26 CEM J-8 June 2008 Complete the following table. Make sure you indicate any relevant stereochemistry. STARTIG MATERIAL REAGETS/ CDITIS CSTITUTIAL FRMULA(S) F MAJR RGAIC PRDUCT(S) 4 C 3 C 2 CC 2 C 3 C 3 C 2 C 1. SCl 2 2. C 3 C 2 C 3 C 2 C 2 C 2 C 2 C C 3 C2 C 2 C 2 C 2 C 3 C 3 C C C3 + C 3 C C 3 C Cl 2 C 3 C C 1. LiAl 4 / dry ether 2. / 2 C 2

27 CEM J-10 June 2008 The structure of methyl 4-aminobenzoate, (E), is given below. 5 (E) b 2 a Give the molecular formula of compound (E). C ame the functional groups in molecule (E) indicated by the boxes a and b. a: amine b: ester Give the structure(s) of all organic products formed when compound (E) is treated with the following reagents. If no reaction occurs, write REACTI. cold Cl (1 M) o hydrolysis of the ester under these conditions. The amine group will be protonated by the strong acid. 3 hot a (4 M) Treatment with base will lead to hydrolysis of the ester. In the basic solution, the carboxylic acid will be deprotonated and the amine will not be protonated. + C 3 2 hot Cl (4 M) ydrolysis of ester. In acidic conditions, the carboxylic acid will not be deprotonated and the amine group will be protonated. + C 3 3

28 CEM ovember 2008 The structure of the antihistamine, Zyrtec TM, is given below. 5 What is the name of the functional group in Box A? Amine (tertiary) What is the name of the functional group in Box B? Ether What is the name of the functional group in Box C? Carboxylic acid 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 LiAl 4 followed by dilute acid. LiAl 4 will reduce the carboxylic acid all the way to an alcohol.

29 CEM J-7 June 2007 Draw the structure of the major organic product formed in the following reactions C 3 MgBr 2. / 2 C 3 C 3 C 2 / 1. ab 4 2. / 2

30 CEM J-8 June 2007 Suggest reagents you could use to achieve the following transformations. A C 3 a 4 B Br C intermediate compound D A: a / 2 / heat B: 2 / Pd catalyst C: Mg / dry ether D: 1.C 2 2. / 2

31 CEM J-10 June 2007 The amino acids serine and valine are shown below. 2 serine C C valine 7 List the substituents attached to the stereogenic centre of valine in order of decreasing priority. highest priority - 2 -C -C(C 3 ) 2 - lowest priority Assign the absolute configuration of the stereoisomer of valine shown above. (S) (anticlockwise) Draw a dipeptide formed by the condensation of serine with valine. 2 C C 2 C C C What are the two key elements of protein secondary structure? The secondary structure describes the orientation of segments of the peptide chain and is defined by the -bonding between amino acid residues. The most common secondary structures are: - α-helices, right handed coils stabilized by -bonds between amide - and C= groups four residues apart and - β-pleated sheets, extended structures stabilized by -bonds between amide - and C= groups on different chains

32 CEM ovember 2007 The structure of salbutamol, a drug used to treat bronchospasms, is given below. 5 Give the molecular formula of salbutamol. C 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 = ; 12 C = ; 16 = ; 14 = ] The molar mass of C is (C) () () () Answer: Give the structure(s) of the major organic products formed when salbutamol is treated with the following reagents. cold Cl (1 M) a (1 M) Cr /

33 CEM ovember 2007 Complete the following table. Starting material Reagents / Conditions Major organic product(s) 2 C SCl 2 C Cl 1. ab 4 2. / 2 TE REMAIDER F TIS PAGE IS FR RUG WRKIG LY.

34 CEM ovember 2007 Consider the reaction sequence below. 2 Cl Draw the structures of products A and B. A + B A B Cl Draw the structure of the product, C, from the following reaction. 3 C C 3 excess 2 Pd/C catalyst C 3 Product C undergoes hydrolysis when heated with 4 M a. Give the structures of the products (in their correct ionic states) formed in this reaction. C 3

35 CEM ovember 2007 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 3 Cl + 2 Cl + TE REMAIDER F TIS PAGE IS FR RUG WRKIG LY.

36 CEM J-7 June 2006 Draw the structure of the major organic product formed in the following reactions. 5 SCl 2 Cl 1. LiAl 4 2. / 2

37 CEM J-10 June 2006 The amino acid serine is shown below: (c) 6 2 (a) C (b) List the substituents attached to the stereogenic centre in order of decreasing priority. highest priority lowest priority 2 C C 2 Assign the absolute configuration of the stereoisomer shown above. S Draw the dipeptide formed by the condensation of two serine residues. 2 C C C C C 2 C 2 Explain briefly what is meant by the primary structure of a protein. The primary sequence is the sequence in which the amino acids occur. For example, ala-ser-tyr: Draw the repeating unit of the polymer formed in the following reaction. 2 Cl Cl n

38 CEM ovember 2006 The structure of lignocaine, a local anaesthetic, is given below. 7 a b Give the molecular formula of lignocaine. C ame the functional groups in lignocaine indicated by boxes a and b. a: amide b: tertiary amine Give the structure(s) of all organic products formed when lignocaine is treated with the following reagents. If no reaction occurs, write REACTI. cold Cl (1 M) hot a (4 M) 2 hot Cl (4 M) 3

39 CEM ovember 2006 Draw the constitutional formula of the major organic product formed in each of the following reactions. 6 SCl 2 Cl C 3 C / heat Cr / C 1. LiAl 4 2. / 2

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