Unit 2 Review: Organic Chemistry. 1. Terms for which you should be able to write or apply the definitions:

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1 Unit 2 Review: Organic Chemistry 1. Terms for which you should be able to write or apply the definitions: organic compound aliphatic hydrocarbons saturated miscible functional group aromatic hydrocarbons unsaturated polymer 2. Write the IUPAC names for the following organic molecules: a) acetone: d) acetylene: b) acetic acid: e) toluene: c) formic acid: f) isopropyl alcohol: 3. Be able to use physical or chemical properties to distinguish between organic substances. For example, identify one physical or chemical property you could use to distinguish between the following pairs of organic substances: a) 2-butanol and 2-methyl-2-propanol: b) cyclopentane and cyclopentene: c) butane and 1-butanol: d) ethanol and 1-decanol: e) butanal and butanone: f) butanal and butanoic acid: 4. Be able to recognize and predict the products for the following types of reactions: Type of Reaction combustion substitution addition dehydration oxidation elimination reactions of alcohols formation of ethers (condensation) formation of esters (condensation) addition polymerization How to Recognize this Type of Reaction 5. Write balanced chemical reactions for the following combustion reactions. Include the states of all reactants and products. a) 2-butanol b) 3-octene c) cyclopropane d) phenol

2 Practice Multiple Choice Questions: 1. A molecule with the formula C 6 H 12 is: a) benzene c) cyclohexene b) hexyne d) cyclohexane 2. A cycloalkene would have the general formula: a) C n H 2n+2 c) C n H 2n b) C n H 2n-2 d) C n H n 3. How many actual double bonds does the benzene ring possess? a) none c) 2 double bond b) 1 double bonds d) 3 double bonds 4. The IUPAC name for the molecule shown to the right is: a) 1,1,1,3-tetramethylpentane b) 1,1,3-trimethylhexane c) 2,2,4-trimethylhexane d) 2,4,4-trimethylnonane 5. The correct name for 4,5-diethyl-2-hexene is: a) 2,3-diethyl-4-hexene c) 4-ethyl-5-methyl-2-hexene b) 4-ethyl-3-methyl-5-heptene d) 4-ethyl-5-methyl-2-heptene 6. Two structural isomers of a saturated hydrocarbon: I) have the same structure II) may display cis/trans (geometric) isomerism III) have the same molecular formula IV) react vigorously to neutralize each other a) I and II only c) II and III only b) III and IV only d) III only 7. Which of the following hydrocarbons does not have isomers? a) C 4 H 8 c) C 3 H 8 b) C 5 H 10 d) all of these molecules have isomers 8. A saturated isomer of cis-3-hexene is: a) 2-methylpentane c) 3-methylpentane b) cyclohexane d) trans-3-hexene 9. Which one of the following compounds is an isomer of CH 3 CH 2 CH 2 CH 2 OH? a) CH 3 CH 2 CH 2 OH c) CH 3 CH 2 O CH 2 CH 3 b) CH 3 CH 2 CH 2 CHO d) CH 3 CH 2 CH 2 CH For which of the compounds below are cis-trans isomers possible? I) CH 3 CH=CH 2 II) CH 3 CH=CHCH 2 CH 3 III) CH 3 CH=CHCH 3 a) I only c) II and III only b) II only d) I, II and III

3 11. Which one of the following is a secondary alcohol? a) CH 3 CH 2 OH c) CH 3 OH b) CH 3 CH(OH)CH 3 d) CH 2 (OH)CH 2 CH 2 CH 2 OH 12. What is the name of the following compound? a) 1,3-dibromophenol b) 1,5-dibromo-6-phenol c) 2,6-dibromophenol d) para-dibromophenol 13. What is the common name for ethyne, CH CH? a) acetylene c) propylene b) dicarbon hydride d) formalin 14. What is the IUPAC name for the acid used to make vinegar? a) acetic acid c) ethanoic acid b) muriatic acid d) formic acid 15. Which of the following molecules contains a tertiary carbon? a) b) c) d) 16. What is one very distinct property of esters? a) they turn red litmus paper blue c) they form waxy solids at SATP b) they turn blue litmus paper red d) they often have fruity odours 17. What is the three-dimensional shape around the oxygen atom in the ether shown below? a) linear c) trigonal planar b) bent d) tetrahedral 18. Which is NOT a property of alcohols? a) alcohols react with other alcohols to produce esters b) the solubility of primary alcohols in water decreases as the length of the alkyl chain increases c) the hydroxyl group of an alcohol makes the molecule polar d) due to hydrogen bonding, boiling points of alcohols are much higher than those of their parent alkanes 19. The structure of cortisone (a steroid hormone) is shown to the right. Which functional groups are found in cortisone? a) ether, alkene, alcohol b) alcohol, ketone, aldehyde c) alcohol, ketone, alkene d) ether, carboxylic acid, ketone

4 20. Which of the following substances can be used to identify unsaturated hydrocarbons? a) bromine water c) litmus paper b) phenolphthalein d) sulfuric acid and heat 21. What is the three dimensional shape around a tertiary carbon? a) trigonal planar c) tetrahedral b) trigonal pyramidal d) bent 22. The correct name for the molecule to the right is a) 2-hydroxy-4-bromo-5-methylhexane b) 3-bromo-2-methyl-5-hexanone c) 4-bromo-5-methyl-2-hexanol d) 3-bromo-2-methyl-5-hexanol 23. Which of the following is 3-chloro-3-ethylhexane? a) c) b) d) 24. Bromine will remain orange with which of the following substances? I) cyclohexanol II) propyne III) trans-2,3-dimethyl-2-butene IV) cis-3,4-dichloro-4-octene a) I only c) III and IV only b) II only d) II, III and IV only 25. The molecule to the right would be classified as: a) an amide b) an amine c) an amino acid d) an aliphatic hydrocarbon 26. What is the three dimensional shape around the carbon atom of a carboxyl group? a) T-shaped c) trigonal planar b) bent d) trigonal pyramidal R 27. How many molecules of CO 2 are produced when 1 molecule of phenol is completely burned? a) 3 c) 6 b) 5 d) The reaction shown to the right is an example of: a) a substitution reaction b) an addition reaction c) an elimination reaction d) a dehydration reaction + HNO 2 (aq) NO 2 + H 2 (g)

5 29. Give the IUPAC name for CH 3 OCH 2 CH 3 a) dimethyl ether c) ethoxymethane b) methoxyethane d) propyl ether 30. Which of the following statements applies to ALL of these molecules? I) they are all structural isomers of one another II) they are all polar molecules III) they are all soluble in water IV) they are all capable of hydrogen bonding a) I only c) I and II only b) I, II and III only d) I, II, III and IV 31. The complete name for the molecule shown to the right is: a) chlorofluoroethene c) cis-1-chloro-2-fluoroethene b) 1-chloro-2-fluoroethene d) trans-1-chloro-2-fluoroethene 32. The IUPAC name for the compound below is: a) pentylamine b) 2-pentanamine c) 2-pentylamine d) 2-aminopentane 33. Which of the following is/are correct IUPAC names for the molecule to the right? a) meta-cyclohexanediol b) 1,2-cyclohexanediol c) ortho-cyclohexanediol d) both b and c are correct names 34. Consider the following pairs of liquids. Which pairs are miscible in each other? I) benzene and hexane II) water and methanol III) water and hexane a) I only c) I and II only b) II only d) I, II and III 35. Select the IUPAC name for the compound below: a) 1,4-dimethylhexanoic acid b) 2,5-dimethyl-1-hexanoic acid c) 1-hydroxy-2,5-dimethylhexanal d) 2,5-dimethylhexanoic acid 36. Which of the following will undergo an addition reaction with chlorine? a) CH 3 CH 2 CH 2 NH 2 c) CH 3 CH 2 CH=CHCH 3 b) C 6 H 6 d) CH 3 CH 2 OH

6 37. Select the best name for the molecule to the right: a) meta-chlorobenzoic acid b) ortho-chlorobenzaldehyde c) para-chlorobenzoate d) meta-chlorosalicylic acid 38. The common name for the molecule shown below is: a) isopropyl alcohol b) formaldehyde c) acetone d) isopropanone 39. The best classification for the following compound is: a) aldehyde b) ester c) ketone d) ether 40. The IUPAC name for the compound below is: a) ethyl pentanoate b) pentyl acetate c) pentyl ethanoate d) ethyl butanoate 41. The compound illustrated below is named: a) 2-methyl-4-ethyl-2-hexanamide b) 3-ethyl-5-methyl-hexanamine c) 4-ethyl-2-methyl-2-hexanamine d) 3-tert-butylaminopentane 42. Which of the following statements is FALSE regarding the initial reaction between Cl 2 and C 2 H 6? a) it is a substitution reaction b) the organic product of this reaction is C 2 H 5 Cl c) the reaction can be initiated with either sunlight or heat d) this reaction is commonly used as a test for saturation 43. What is the expected product of the reaction between 2-butene and Cl 2? a) 1-chlorobutene c) 2-chlorobutane b) 2,3-dichlorobutane d) 2,3-dichlorobutene 44. An elimination reaction of an alcohol leads to the formation of a(n): a) alkene c) alkane b) cycloalkane d) aromatic compound 45. What is the first intermediate product when ethanol is oxidized with a mild oxidizing agent? a) CH 3 COOH c) CO 2 b) CH 3 CHO d) CH 3 OCH Which of the following alcohols forms a ketone when it is oxidized? a) 1-propanol c) methanol b) 2-methyl-2-propanol d) 2-propanol

7 47. The organic starting materials for the preparation of an ester are: a) a carboxylic acid and an alcohol c) a ketone and an alcohol b) an alkane and a ketone d) two alcohols 48. What two molecules were reacted to form the molecule to the right? a) ethanol and methanol c) propanol and sulfuric acid b) methanol and ethanoic acid d) ethanol and methanoic acid 49. The reaction below can be classified as a(n): I) hydration reaction II) esterification reaction III) addition reaction IV) condensation reaction + + a) I only c) II and IV only b) I and II only d) II, III and IV only 50. Which of the following statements is/are true about this molecule: I) it is immiscible in water II) it has a distinctive fishy odour III) it is an electrolyte IV) its melting point will be higher than propane s melting point a) I only c) II and III only b) I and II only d) II and IV only 51. Which of the following compounds will have the highest melting point? a) c) b) d) 52. Which of the following monomers can undergo addition reactions to form polymers? I) II) III) IV) a) I and II only c) II and IV only b) I and IV only d) I, II, III and IV 53. Which of the following is/are polymers? a) polyethylene c) cellulose used to make paper b) the protein in fingernails (keratin) d) all of the above

8 54. Which of the following statements is/are true about the reaction below? + H 2 O (aq) + I) this is an addition reaction II) this is an oxidation reaction III) this is a substitution reaction IV) this is an elimination reaction a) I and II only c) II and IV only b) II and III only d) I, II, III and IV 55. In order for a molecule to be able to polymerize by condensation reactions, it must have: a) a double or triple bond b) two functional groups, such as an alcohol, amine or carboxylic acid c) halogen atoms d) a phenyl (benzene) side chain 56. It is possible to distinguish 2-propanol from 2-methyl-2-propanol by the following test: a) 2-propanol reacts with Na 2 Cr 2 O 7 (aq) while 2-methyl-2-propanol does not b) 2-propanol reacts with Br 2 (in water) while 2-methyl-2-propanol does not c) 2-propanol combusts while 2-methyl-2-propanol does not d) all of the above 57. It is possible to distinguish propanal from propanone by the following test: a) propanal is miscible in water while propanone is not b) propanal has a much higher melting point than propanone c) propanal will undergo an oxidation reaction with NaCr 2 O 7 while propanone will not d) propanal will form an ester with an organic acid while propanone will not 58. A carboxylic acid can be distinguished from an alkene because: a) the acid will have a higher melting point than the alkene b) the acid will dissolve in water while the alkene will not c) the alkene will react with KMnO 4 while the acid will not d) all of the above could be used to distinguish between a carboxylic acid and an alkene 59. An unknown organic substance does not dissolve in water and turns bromine in water colourless. This substance is probably: a) a carboxylic acid c) a tertiary alcohol b) a ketone d) an alkyne 60. Which of the following are chemical properties of alkenes? a) will turn bromine water from purple to brown b) will turn KMnO 4 solution from yellow to colourless c) will under-go an addition reaction with H 2 O in the presence of a sulfuric acid catalyst d) all of the above are chemical properties of alkenes 61. C 2 H 6 would dissolve best in: a) water c) benzene b) methanol d) propanal

9 Identify the family (type) of each organic compound and write its IUPAC name br

10 Draw the following organic compounds: 2,3-dichlorobutane cyclohexanol 1-butyne methoxyethane 2,3-dibromocyclopentanone isopropylbenzene methylbenzoate 4-ethyl-2-hexanone 2-ethylhexanoic acid 1,4-dichlorobenzene 2-methylbutanal 2-methyl-2-pentanol 3-iodocyclooctene butylpropanoate 1,1-diethylcyclopropane 2-ethoxypropane 6. Identify the functional groups in acetominophen (Tylenol), shown to the right. Explain why Tylenol is a solid at SATP. 7. Predict 2 chemical and 2 physical properties of isopropyl alcohol.

11 a) Draw the structural formulas for the products of the following reactions (if any). Some reactions will not proceed. Do not balance these reactions or include states. Name the organic products. Classify each reaction as many ways as possible (addition, elimination, dehydration, condensation, oxidation and/or substitution). + H 2 (g) Pt catalyst b) + [O] c) + Cl 2 (g) (excess) d) + [O] e) + H 2 O (l) f) + Br 2 (l) FeBr 3 g) + [O] h) + i) + j) + KMnO 4 NaOH

12 k) l) m) + HCl (aq) n) + Br 2 (l) o) p) + [O] q) + [O] r) + NH 3 (g) s) + KMnO 4 NaOH t) n F catalyst