+ (CH 3) 2 NH + Cl - CHEM1907/ J-6 June Complete the following table. CONSTITUTIONAL FORMULA(S) OF MAJOR ORGANIC PRODUCT(S)

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1 EM1907/ J-6 June 2003 omplete the following table. AME (where required) DITIS STITUTIAL FRMULA(S) F MAJR RGAI PRDUT(S) 13 l excess ( 3 ) 2 + ( 3) 2 + l - ame: 3 M l / heat + excess 3 + / heat 3 3

2 EM1907/EM J-6 June 2004 omplete the following table. Make sure you complete the name of the starting material where indicated. AME (where required) ( 3 ) 2 DITIS STITUTIAL FRMULA(S) F MAJR RGAI PRDUT(S) 13 1 conc. l / heat + ( 3 ) 2 + l - 1. Sl 2 / heat 2. excess 3 2 ame: pentanal S 4 (catalyst) heat 3 3 catalyst 3 + 3

3 EM1907/ J-5 June 2005 omplete the following table. Make sure you complete the name of the starting material where indicated. 5 AME (where required) DITIS STITUTIAL FRMULA(S) F MAJR RGAI PRDUT(S) ame: 2-pentanone 3 1. LiAl 4 / dry ether 2. / M a / heat conc. l / heat [Ag( 3 ) 2 ] / dil.

4 EM J-6 June 2006 omplete the following table. Make sure you complete the name of the starting material where indicated. AME (where required) DITIS STITUTIAL FRMULA(S) F MAJR RGAI PRDUT(S) 8 ame: butanoic acid (or butyric acid) Sl 2 l r / + ame: 2-methylbutyraldehyde (or 2-methylbutanal) 2 S 3 M a / heat + S 1 M l / heat +

5 EM J-5 June 2007 omplete the following table. Make sure you complete the name of the starting material or major product where indicated. DITIS STITUTIAL FRMULA(S) F MAJR RGAI PRDUT(S) ab / r / + ame: 3- methylcyclohexanone ame: propyl acetate M a / heat excess

6 EM J-5 June 2008 omplete the following table. Make sure you indicate any relevant stereochemistry. DITIS STITUTIAL FRMULA(S) F MAJR RGAI PRDUT(S) Sl dilute conc. 2 S 4 catalyst l 2 3

7 EM J-10 June 2008 Aniline, benzoic acid and benzamide are all insoluble in water, but soluble in ether. Explain how, by using simple laboratory reagents and equipment, each compound could be separated and recovered from a mixture of all three aniline benzoic acid benzamide All of the compounds are neutral and will dissolve in an organic solvent like ether. Benzoic acid is a weak acid and will react with a strong base to form an anion which will dissolve in water. Aniline is a weak base (whereas benzamide is a very weak base) and will be deprotonated by reaction with a strong acid to form a water soluble cation. 2 2 dissolve in ether, add 2 M a ether layer 2 2 aqueous layer 2 add 2 M l add 2 M l aqueous layer ether layer 3 add 2 M a 2 evaporate the ether filter off the crystals or extract into ether and evaporate to dryness 2 extract into ether and evaporate to dryness

8 EM J-6 June 2009 omplete the following table. Make sure you complete the name of the starting material or major product where indicated. 6 DITIS STITUTIAL FRMULA(S) F MAJR RGAI PRDUT(S) l ame: phenyl acetate [Ag( 3 ) 2 ] / 3 M a / heat + ame: cyclopentanone excess 3 / cat. heat 3 3

9 EM J-8 June 2009 Morphine is the principal active agent in opium and is a highly potent analgesic drug. Its structure and conversion into codeine (a moderate analgesic) and pholcodine (a cough suppressant) are shown below. 7 * * * * * 3 morphine reagent B intermediate A 3 I codeine pholcodine 3 Give the molecular formula of morphine ow many stereogenic (chiral) centres are there in morphine? 5 (* on picture) Identify the functional groups present in morphine. phenol, amine, alcohol, ether, alkene Draw the structures of codeine and reagent B. codeine reagent B 3 I 3

10 EM J-6 June 2010 omplete the following table. Make sure you complete the name of the starting material where indicated. DITIS STITUTIAL FRMULA(S) F MAJR RGAI PRDUT(S) 6 l excess l / 2 / heat ame: cyclohexanone