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12 U – Organic Chemistry Test Review Test Date: Readings “Gold in Your Gas Tank” booklet – fractional distillation and cracking Polymer booklets – natural polymers, creation and destruction of plastics Theory Questions 1. Explain the difference between organic and inorganic compounds. 2. What’s so special about carbon? 3. How could you test to determine whether a hydrocarbon is saturated or unsaturated? 4. Determine the chemical formula for the following hydrocarbons: a) an alkane with 8 carbons c) an alkyne with 13 carbons b) an alkene with 20 carbon c) a cycloalkane with 5 carbons 5. Explain the term “homologous series.” 6. How can you tell the difference between a “cis” and “trans” isomer? In what types of hydrocarbons can they be found? 7. What is an aromatic compound, and what is the simplest aromatic structure? 8. Do aromatic hydrocarbons react more than saturated or unsaturated hydrocarbons? Explain why. 9. What is a nucleophile? Which of all the nucleophiles is the most reactive? The least? 10. What is a photochemical reaction? Give an example of a hydrocarbon that undergoes this type of reaction. 11. How do alkyl halides compare to alkanes in terms of reactivity, solubility, and boiling point? 12. Describe Markovinov’s rule in addition, and the carbon rule in elimination. 13. Describe common uses/applications of each of the 8 functional groups. 14. Why are ketones slightly more soluble than aldehydes? 15. Which functional groups are acidic? Basic? 16. Arrange the following in order of increasing boiling point and explain your reasoning: propanoic acid, propanol, propanal, propanone, methoxyethane, propane, propan-1-amine 17. Arrange the following in order of increasing solubility and explain your reasoning: octan-1-amine, ethanol, butanone 18. What is the difference between oxidation and reduction reactions? 19. Why do tertiary alcohols not undergo oxidation? 20. Why are condensation and hydrolysis considered opposite reactions? 21. What are the two types of synthetic polymers? 22. What is a “cross-link” and how does it affect polymer properties? *Please note that the above theory questions are just a way to review material straight out of your notes. Just because something from your notes was not mentioned above, does not mean it could not appear on the test. Review your notes!* Nomenclature 1. Name the following organic compounds. CH2 CH2 H3C CH3 CH O CH H3C CH2 C CH3 CH CH3 a) CH3 OH b) C CH2 d) H3C H3C O CH2 CH CH3 CH Cl C HC Cl CH2 f) H3C CH OH O CH2 CH CH HC e) OH CH3 c) CH3 O H3C H3C HC C CH3 CH2 CH2 NH C CH2 CH CH3 CH CH2 CH H2C CH3 CH2 CH O CH3 h) CH3 CH3 CH2 CH2 H3C g) O CH3 i) CH3 CH3 H3C H3C CH2 CH2 CH2 N CH2 H3C H3C H2C CH CH2 H3C j) C C C C CH3 k) H3C l) Br CH2 H2C CH3 m) H3C CH2 CH2 O C CH2 CH CH CH2 CH2 CH3 CH3 Br Br H3C CH2 CH CH2 o) H2N Br n) H3C Br C CH2 CH2 CH2 NH2 O O OH H3C HC O CH CH2 C CH2 CH3 Cl p) H3C q) CH2 OH OH CH CH CH Cl C HC CH3 HC H3C Cl CH CH2 H2C r) CH2 CH2 2. Draw the following organic compounds. a) hex-2,4-diene j) b) propyl 3-methylpentanoate k) 5-phenyloctan-2-one c) 1,3,4-trichlorocyclobutane l) d) 1-butoxypentane m) cyclopropanol e) N-ethylpentan-2-amine n) N-2-methylbutylpentanamide f) o) 2-ethoxy-3-methylhexane 2,3,3-trimethylhexanal pentan-1,5-dioc acid 3-ethyl-3-methylhexane g) N-methyl-N-propylethanamide p) 2-bromopropyl benzoate h) 4-bromohept-2-yne q) 4-hydroxybutanoic acid i) r) 2,4,6-trimethylphenol polypropene Reactions 1. Complete the following reactions – draw the reactants and products, show the mechanism and conditions, and name the products. These reactions are one step. a) Butanone + [O] → l) b) Propene + H2 → m) benzene + 2-chloropropane → c) Toluene + Nitric Acid → n) butan-1-ol + O2 → d) Ethanol + Butan-2-ol → o) methanol + [O] → e) N-propylpentanamide + H2O → p) hexanoic acid + butan-2-ol → f) q) 3,3-dimethylpentanal + [H] → 3-methylbutanoic acid + N-ethylpropan-1-amine 2-methylbutyl butanoate + H2O → g) 3,3-dichlorobutanal + [O] → r) 2,3-dichlorobutane + NaOH → h) Butanoic Acid + [H] → s) 2-methylpropane + I2 → i) Propan-2-ol + Hydrogen Bromide → t) j) trans-pent-2-ene + H2O → u) N-ethylbutan-2-amine + bromoethane → k) Pent-1-yne + Hydrogen Chloride → Pentan-2,4-dione + [H] → v) Hexan-2-5-diol → *Make polymers of the next three sets of reactants* w) Propan-1,3-dioic acid + butan-1,4-diol → x) Trans-butene → y) Pentan-1,5-diamine + Ethan-1,2-dioc acid → 2. Determine the synthesis pathway from the reactants to the products. Show the mechanism and conditions for these multi-step reactions. a) b) c) d) e) f) g) h) But-1-ene from butanal Propanoic acid from propan-1-ol N-methylbutanamide from an alkyl halide and an alcohol Ethane from ethanoic acid Propan-2-ol from propane butyl ethanoate from but-1-ene and ethanal 2-ethoxypentane from an aldehyde and a ketone Hexan-2-4-dione from an alkene