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Year 13 Organic Revision Worksheet QUESTION ONE Name the following molecules using IUPAC systematic rules. (a) (b) CH3-CHCl-CH3 O CH3 CH2 C NH2 (c) _____________________________ CH3 _____________________________ H C C H CH3 _____________________________ QUESTION TWO Ethanol is found in alcoholic beverages and can be detected by a breathalyzer test which uses acidified potassium dichromate. (a) Identify, by circling the correct word below, what type of alcohol ethanol is. primary (b) (d) tertiary quaternary Acidified potassium dichromate is a weak oxidising agent in this case, and will not produce a carboxylic acid from the alcohol. Circle the correct organic product from the list below. aldehyde (c) secondary ketone acyl chloride amide The organic product produced in (b) can then be identified by using Tollen's reagent. What would be seen in a positive test with Tollen's reagent? _____________________________________________________ _____________________________________________________ A second alcohol, 2-methyl propan-2-ol, will not give a positive breathalyzer test. Why not? _____________________________________________________ _____________________________________________________ (e) 2-methyl propan-2-ol can be identified with Lucas' Reagent. What is Lucas' Reagent and how is it used to identify tertiary alcohols? _____________________________________________________ _____________________________________________________ (f) Write a balanced chemical equation for the reaction of ethanol with Lucas' Reagent. _____________________________________________________ QUESTION FOUR Fill in the gaps with the correct reactants, products or catalysts in the reactions below. You may draw graphical (structural) formulae or constitutional formulae. If there is more than one organic product, (e.g. due to Markovnikov’s rule), give the major product only. (a) CH3 (b) CH3 CH CH2 + HCl O C O H + CH3 Cl (c) C N CH3 + HCl O CH3 CH2 C H + H+/Cr2O72(organic product only) OH (d) (e) CH3 CH CH3 CH3 CH2 OH + CH3 CH CH2 + H2O CH3CH2Cl + HCl + POCl3 QUESTION FIVE Name the type of reaction shown in question four above: Reaction (a) _______________________ Reaction (c) _______________________ Reaction (d) _______________________ QUESTION SIX (a) Draw a section of the addition polymer formed from cis-but-2-ene. (b) Polyesters can be formed by the reaction between carboxylic acids and alcohols. Name the catalyst for this reaction. ______________________________________ (c) Draw a section of the polymer formed when the two molecules below react to form a polyester. HOOC-CH2-COOH (d) + HO-CH2-CH2-OH What type of molecule could be used instead of a carboxylic acid to remove the need for a catalyst? _______________________________________ (1 mark) QUESTION SEVEN You are given a sample of ethanol and asked to produce ethanoyl chloride. You have access to any chemical reagents and equipment that you need. How would you do this? State all reaction conditions required and write equations for all relevant reactions.