1. True or false: In a molecule, carbon always forms bonds with four other elements. 5. An unsaturated hydrocarbon must contain a or bond.
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1 APTER 20 Organic hemistry 1. True or false: In a molecule, carbon always forms bonds with four other elements. False 2. A triple bond involves sharing electrons. a. 2 b. 3 c. 4 d. 5 e. 6 e ydrocarbons always contain carbon and. hydrogen 4. ydrocarbons are always saturated. T/F False 5. An unsaturated hydrocarbon must contain a or bond. double; triple 6. In a saturated hydrocarbon, the carbon-carbon bond angles are all Write the formula for the saturated alkane that contains five carbon atoms Write the formula for the saturated alkane that contains seven carbon atoms opyright oughton Mifflin ompany. All rights reserved. 259
2 260 hapter Butane has how many structural isomers? a. one b. two c. three d. four e. five b. two 10. ow many types of alkyl groups can arise from propane? a. none b. one c. two d. three e. four c. two 11. A molecule whose name includes trimethyl contains methyl substituents. three 12. Name the following molecule. 2 2-methylbutane 13. Name the following molecule. 2 2,4-dimethylpentane opyright oughton Mifflin ompany. All rights reserved.
3 Organic hemistry Name the following molecule a. 2,2,3,5-tetramethyl-7-propyl-7-t-butyldecane b. 6-propyl-2,6-di-t-butylnonane c, 2,2,5,7,8,8-hexamethyl-3,3-dipropylnonane d. isonanane a. 2,2,3,5-tetramethyl-7-propyl-7-t-butyldecane 15. Name the following molecule. 2 2 a. n-hexane b. isohexane c. 1,2,3-trimethylpropane d. methyl-diethylmethane e. 3-methylpentane e. 3-methylpentane 16. Name the following molecule. -- ( 2 ) 7 a. heptane b. hexane c. octane d. nonane e. decane d. nonane opyright oughton Mifflin ompany. All rights reserved.
4 262 hapter A student gave a molecule the following name: 2-ethyl-3-methyl-5-isopropylhexane owever, her TA pointed out that although the molecule could be drawn correctly from this name, the name violates the systematic rules. What is the correct (systematic) name of the molecule? a. 3,4-dimethyl-6-isopropylheptane b. 2-isopropyl-4,5-dimethylheptane c. 3,4,6,7-tetramethyloctane d. 1,2-diethyl-3,6,7-trimethylheptane e. 2,3,5,6-tetramethyloctane e. 2,3,5,6-tetramethyloctane 18. In lecture, the professor named a molecule 2-ethyl-4-tertiary-butylpentane. An alert student pointed out that although the correct structure could be drawn, the name did not follow systematic rules. What is the correct systematic name for the molecule? a. 2-t-butyl-5-methylhexane b. 2-ethyl-4,5,5-trimethylhexane c. 3,5,6,6-tetramethylheptane d. 2,2,3,5-tetramethylheptane e. undecane d. 2,2,3,5-tetramethylheptane 19. is the carbon skeleton (minus any hydrogen atoms) of I II. a substituted octane III. a compound with 3 tertiary carbons IV. a compound with 3 secondary carbons V. a compound with 2 isopropyl groups a. I, II, III b. II, III, IV c. III, IV, V d. II, IV, V e. I, II, III, IV a. I, II, III opyright oughton Mifflin ompany. All rights reserved.
5 Organic hemistry is the carbon skeleton (minus any hydrogen atoms) of a. 2,4-diethyl-3,6-dimethylheptane b. 2,5-dimethyl-4,6-diethylheptane c. 1,4-diethyl-3,6-dimethyl-tridecane d. 5-ethyl-3,6-trimethyloctane e. 4-ethyl-2,5,6-trimethyloctane e. 4-ethyl-2,5,6-trimethyloctane 21. Name the following molecule ,4-dimethylhexane 22. Draw the structural formula for 2,2-dimethylpropane. 23. Draw the structural formula for 3-ethyl-4-methylheptane Gasoline consists of hydrocarbons with 20 to 30 carbon atoms. T/F False opyright oughton Mifflin ompany. All rights reserved.
6 264 hapter Ethane undergoes dehydrogenation. The product of this undergoes an addition reaction with hydrogen gas. The product of this is a. ethylene b. propane c. butane d. ethane d. ethane 26. Which of the following cannot form alkenes? a. methane b. ethane c. propane d. two of the above e. all of the above a. methane 27. Give the name of the molecule = 2. 2-pentene 28. Give the name of the molecule 2-methyl-2-butene 29. The general name given to hydrocarbons with double bonds is a. alkenes b. alkynes c. alkanes d. unsaturated hydrocarbons e. aromatic hydrocarbons a. alkenes l is named a. 1-chloro-3-pentyne b. 5-chloro-2-pentene c. 1-acetylenyl-3-chloropropane d. 5-chloro-2-pentyne e. 1-chloro-3-pentene d. 5-chloro-2-pentyne opyright oughton Mifflin ompany. All rights reserved.
7 Organic hemistry Name the following molecule a. 1-hexyne b. 2-ethynyl butane c. 2-ethyl-3-butyne d. 3-methyl-1-pentyne e. 3-methyl-4-pentyne d. 3-methyl-1-pentyne 32. Name the molecule 2. 2-pentyne 33. Draw the structural formula for 3-methyl-2-hexene. = Draw the structural formula for 4-ethyl-2-octyne Name the molecule below. l l 1,3-dichlorobenzene or m-dichlorobenzene opyright oughton Mifflin ompany. All rights reserved.
8 266 hapter Draw the structural formula for 2-phenylpropane. 37. Name the following: Br l l l a. 1,1,1-trichloro-5-bromo-3-pentene b. 5,5,5-trichloro-1-bromo-2-pentene c. 1,1,1-trichloro-5-bromo-2-pentene d. 1,1,1-trichloro-5-bromo-3-pentyne b. 5,5,5-trichloro-1-bromo-2-pentene 38. lassify the following molecule. 3 O a. acid b. aldehyde c. amine d. ketone e. carbonyl b. aldehyde 39. Which of the following has the greatest number of -- O bonds? a. ketone b. ester c. alcohol d. amine e. aldehyde b. ester 40. Which of the following has the least number of -- O bonds? a. ketone b. alcohol c. ether d. ester e. Two of the above are equal. b. alcohol opyright oughton Mifflin ompany. All rights reserved.
9 Organic hemistry Esters have sweet, fruity odors. T/F True 42. Give the name for the following molecule. 2 O 2-butanol 43. Write the structural formula for 3-isopropyl-3-heptanol. O Which of the following is known as wood alcohol? a. methanol b. ethanol c. propanol d. isopropanol a. methanol 45. Which of the following is known as rubbing alcohol? a. methanol b. ethanol c. propanol d. isopropanol d. isopropanol 46. Which of the following is found in beverages such as wine? a. methanol b. ethanol c. propanol d. isopropanol b. ethanol opyright oughton Mifflin ompany. All rights reserved.
10 268 hapter Identify the type of organic compound shown. -- = O a. aldehyde b. ester c. amine d. ketone d. ketone 48. Identify the type of organic compound shown. O a. aldehyde b. ester c. amine d. ketone a. aldehyde 49. Name the following compound l O 3-chlorohexanal 50. Name the following compound. O phenylbutanal 51. Draw the structural formula for pentanal O 52. Draw the structural formula for 3,4-dichlorooctanal. opyright oughton Mifflin ompany. All rights reserved.
11 Organic hemistry O l l 53. Name the following compound. O propanone (acetone) 54. The name methanal is the systematic name for a. acetone b. formaldehyde c. rubbing alcohol d. acetaldehyde e. water b. formaldehyde 55. Name the following compound. OO ethanoic acid (acetic acid) 56. Name the following compound. 2 OO l 4-chloro-2-methylpentanoic acid 57. Draw the structural formula for 3-ethylhexanoic acid OO 2 opyright oughton Mifflin ompany. All rights reserved.
12 270 hapter Nylon is an example of a a. copolymer b. homopolymer c. dimer d. two of these a. copolymer 59. Teflon is an example of a a. copolymer b. homopolymer c. dimer d. two of these b. homopolymer opyright oughton Mifflin ompany. All rights reserved.
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