CM 1000/CM 1002/CM2101 Assignment No. 12 Answers to the following problems should be placed in your tutor’s box situated outside Room 225 in the Kane Building by 5 pm Friday 11th March 2005 1. Draw the structure of (a) A primary alkyl chloride, C5H9Cl. (b) A tertiary alkyl iodide, C6H13I. (c) A secondary alcohol, C6H12O 2. Write an equation for each of the following nucleophilic substitution reactions: (a) (b) (c) (d) 3. 1-bromobutane + sodium iodide 2-chloropropane + sodium ethoxide t-butylbromide + methanol n-propyl chloride + ammonia (2 equivalents) Give the products for the following elimination reactions: (a) KOtBu CH3CH2CH2Br (b) Na OCH2CH3 CH3-CH-CH2-CH3 Br (c) CH 3 NaOEt Br EtOH 4. Give the expected organic products from the two following reactions and state which is Markovnikov or anti- Markovnikov addition : (i) Hg(OAc)2 (ii) NaBH4, H2O ? (i) B2H6 (ii) H2O2, NaOH ? 5. Write an equation for each of the following reactions: (a) CH3CH2OH + NaH (b) CH3 H3C C OH CH3 (tert-butanol) + K (potassium metal)