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Name: ________________________________ Organic Reactions Worksheet For the questions below, give full structural diagrams and names for all reactants and products. Also indicate any catalysts/reaction conditions for the reaction. Also indicate the TYPE OF REACTION. 1. Oxidation with primary and secondary alcohols via sulfuric acid and potassium dichromate. a. What is formula for oxidizing agent? b. Using a primary alcohol i) Give the displayed (structural formula) which it could be oxidized to ii) Give the conditions needed to get each product iii) State which homologous series the products are part of iv) Write the balanced equation for each oxidizing reaction, use [O] convention c. Using any secondary alcohol: i) Give the displayed (structural formula) which it could be oxidized to ii) State which homologous series the products are part of iii) Write the balanced equation for each oxidizing reaction, use [O] convention d. What is the reaction for tertiary alcohols? 2. The formation of 2-hexanol from an alkene. 3. The formation of 2,2-pentanediol. 4. The reaction between 3-hexanol and potassium dichromate. What would you visually observe? 5. The reaction between trans-2-hexene with hydrogen bromide. 6. The reaction that would occur if isopropanol was heated at 100°C in acidic conditions. 7. The formation of 2-butanol. 8. The reaction for the complete combustion of C2H4 9. The oxidation of 2-butanol with KMNO4 and K2Cr2O7. Describe the qualitative observations. 10. The oxidation of 1-butanol in a reflux apparatus, describe the qualitative observations. 11. The complete and incomplete combustion of 2-pentanol (incomplete will have both CO and C in addition to carbon dioxide). How would the flame colors differ? 12. Show the formation of 2-butene from an alcohol Show the MAJOR product, and just name of the minor product. 13. Show the reaction between water and cyclohexene. Name: ________________________________ 1. a K2Cr2O7 Organic Reactions Worksheet ANSWERS B i. displayed formula with – CHO (aldehyde); displayed formula with – COOH group ii Gives aldehyde after mild heat and distilling immediately; gives carboxylic acid after refluxing with excess oxidising agent. iii aldehydes; then carboxylic acids iv e.g. CH3CH2OH + [O] → CH3CHO + H2O e.g. CH3CH2OH + 2[O] → CH3COOH + H2O c i displayed formula with >C=O group (ketone) ii ketones iii e.g. CH3CHOHCH3 + [O] → CH3COCH3 + H2O e. NO H atom on C atom that attaches to the –OH functional group 2. The formation of 2-hexanol from an alkene. + H2SO 4 H2O OH 100 C 1-hexene 2-hexanol Addition Reaction 3. The formation of 2,2-pentanediol. OH + H2SO4 2 H2O 1-pentyne 100 C OH 2,2-pentanediol Addition Reaction 4. The reaction between 3-hexanol and potassium dichromate. What would you visually observe? K 2 Cr 2 O 7 + H2O O OH 3-hexanone 3-hexanol dichromate changes from orange to green Oxidation Reaction 5. The reaction between trans-2-hexene with hydrogen bromide. Br + + HBr trans-2-hexene hydrogen bromide 2-bromohexane Br 3-bromohexane Addition Reaction 6. The reaction that would occur if isopropanol was heated at 100°C in acidic conditions. HO H2SO4 + H2O 100 °C propene isopropanol Elimination Reaction 7. The formation of 2-butanol. + H2SO4 H2O OH 100 °C 2-butanol 1-butene Addition Reaction -could also use 2-butene 8. The reaction for the complete combustion of C2H4 : Answer C2H4 + 3 O2 2 CO2 + 2 H2O 9. The oxidation of 2-butanol with KMNO4 and K2Cr2O7. Describe the qualitative observations. Name: ________________________________ O KMnO4 OH + H2O butanone 2-butanol - KMnO4 changes from purple to brown - K2Cr2O7 will change from orange to green Oxidation Reaction 10. The oxidation of 1-butanol in a reflux apparatus. Show any intermediates formed and describe the qualitative observations. O KMnO4 OH + O KMnO4 H2O 2 H+ butanoic acid butanal 1-butanol + HO - KMnO4 changes from purple to brown (K2Cr2O7 will change from orange to green) Oxidation Reaction 11. The complete and incomplete combustion of 2-pentanol OH + 2-pentanol OH 2-pentanol 15/2 O O 5 O O C + 6 H2O C + Complete Combustion + 6 O O 3 O C O + C O + 6 H2O Incomplete Combustion 12. Show the formation of 2-butene from an alcohol Show the MAJOR product, and give the name minor OH H2SO4 100 °C 2-butanol + H2O 2-butene Elimination Reaction - also produce 1-butene Figure 1 also called dehydration 13. Show the reaction between water and cyclohexene. OH H2SO4 + H2O 100 °C Addition Reaction