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CHAPTER 11 INTRODUCTION TO ORGANIC CHEMISTRY MULTIPLE CHOICE QUESTIONS 11.1 E The general formula for alkenes is: A. CnH2n+2 B. C2nH2n C. CnHn+2 D. CnH2n E. CnH2n ─2 D. CnH2n+4 E. CnH2n ─4 Answer: D 11.2 E The general formula of an alkane is: A. CnH2n B. CnH2n+2 C. CnH2n ─2 Answer: B 11.3 E Which one of the following formulas is that of an unsaturated hydrocarbon? A. B. C. D. E. CH3 ─ CH2 ─ CH3 CH3 ─ CH = CH2 CH3 ─ CH2 ─ OH CH3 ─ O ─ CH2 ─ CH3 CH3─ CH3 Answer: B 11.4 E Which molecule represented below is unsaturated? A. C3H8 B. CH3OH C. C5H10 D. CH4 E. C4H10 Answer: C 11.5 E The formula CH3CH2CH2CH2CH2CH = CH2 represents: A. an alkane E. a CFC B. an alkyne C. an alcohol D. an unsaturated hydrocarbon Answer: D 11.6 M Which one of the following hydrocarbons does not have structural isomers? A. C7H16 B. C6H14 Answer: E C. C5H10 D. C4H8 E. C3H8 CHAPTER 11: ORGANIC CHEMISTRY 11.7 M How many structural isomers are there of C4H10? A. 4 B. 6 C. 2 D. 8 E. 10 Answer: C 11.8 E Which of the following are structural isomers of hexane? 1. 2. 3. 4. A. 1 and 2 Answer: D B. 1 and 3 C. 2 and 3 D. 2 and 4 E. 3 and 4 187 188 CHAPTER 11: ORGANIC CHEMISTRY 11.9 M Which of the following pairs are geometric isomers? A. B. C. D. CH3CH2 ─ O─ CH2CH3 and CH3CH2CH2CH2OH Cl | CH3─ CH ─ CH─CH3 and ClCH2CH2CH2CH2Cl | Cl Cl | CH3CH2C = CH and CH3 ─ C=C ─ CH2Cl | | | Cl Cl H H | CH2Cl─ C = C─ H and CH2Cl ─ C = C─ H | | | H CH2Cl CH2Cl Answer: D 11.10 E The two molecules represented below are examples of A. structural isomers B. isotopes E. unsaturated hydrocarbons C. alcohols D. carboxylic acids Answer: A 11.11 E The two molecules represented below are examples of CH3 ─ CH2 ─ O─ CH2CH3 A. isotopes. B. structural isomers. E. unsaturated hydrocarbons. CH3CH2CH2CH2 ─ OH C. alcohols. D. carboxylic acids. Answer: B 11.12 E Which of the following is an aromatic compound? A. C2H2 B. C6H12 Answer: C C. C6H4Br2 D. C5H10 E. C2H4Br2 CHAPTER 11: ORGANIC CHEMISTRY 11.13 E The compound that has a triple bond between one pair of carbon atoms is called a/an: A. alkane B. chlorofluorocarbon C. alkyne D. alkene E. alcohol Answer: C 11.14 E The alkane with six carbon atoms is called A. butane. B. heptane. C. hexane. D. butene. E. none of these Answer: C 11.15 M What is the systematic name for the compound represented below? A. B. C. D. E. 2-ethylbutane 3-methylpentene 3-methyl-1-pentene 3-methyl-1-hexene 2-methylhexane Answer: C 11.16 H The systematic name for the compound represented below is A. B. C. D. E. 4,5-diethylheptane 3-propyl-4-ethylhexane 3-ethyl-4-propylhexane 3-methyl-4-propylheptane 2-ethyl-4-propylhexane Answer: D 189 190 CHAPTER 11: ORGANIC CHEMISTRY 11.17 M Which is the systematic name for the compound represented below? A. B. C. D. E. 2,3-dibromopentane 1,2-dibromopentane 2,3-dibromopropane 1,2-dibromopropane 1,2-propane dibromide Answer: D 11.18 M The correct structure for 2,3,3-trimethylpentane is CH3 CH3 | | A. CH3 ─CH ─ C ─ CH2CH3 | CH3 CH3 CH3 | | B. CH3─C ─ CH─CH2CH3 | CH3 C. CH3─ CH─ CH─ CH─ CH3 | | | CH3 CH3 CH3 D. CH3─ CH─ CH─ CH2─ CH3 | | CH3 CH2 ─ CH3 Answer: A 11.19 M The group of atoms that is responsible for the characteristic properties of a family of organic compounds is called a/an ________ group. A. hydrocarbon Answer: B B. functional C. ether D. enzyme E. polyatomic ion CHAPTER 11: ORGANIC CHEMISTRY 11.20 M Organic compounds with the general formula R─ O─ R (where R is an alkyl group) are called: A. alkenes. B. alcohols. C. ethers. D. aldehydes. E. organic acids. Answer: C 11.21 M Which one of the following represents a carboxyl functional group? A. B. C. D. E. ─OH Answer: D 11.22 M Which one of the following is the formula for a ketone? A. CH3CHO Answer: C B. CH3OCH3 C. CH3COCH3 D. CH3COOH E. HCºCH 191 192 CHAPTER 11: ORGANIC CHEMISTRY 11.23 M Which one of the following represents an ester functional group? A . B. C. D. Answer: B 11.24 M Wood alcohol is the common name for A. methanol. B. ethanol. C. propyl alcohol. D. ethylene. E. acetylene. Answer: A 11.25 M Which type of organic compound does not contain a carbonyl group? A. ethers B. carboxylic acids C. ketones D. aldehydes E. esters Answer: A 11.26 M Acetylene, C2H2, the simplest alkyne, can be prepared from "inorganic" materials. Which reaction below is used to prepare acetylene in this way? A. B. C. D. 2C + H2 C2H2 C2H4 C2H2 + H2 2CO + 2H2O C2H2 + H2O2 CaC2 + 2H2O C2H2 + Ca(OH)2 Answer: D CHAPTER 11: ORGANIC CHEMISTRY 11.27 M Which one of the following compounds will result from the addition of HCl to CH3─ CH=CH2 ? A. B. C. D. E. CH3Cl + CH2= CH2 CH3─ CHCl=CH2 CH3─ CHCl─CH3 CH3─ CH2─CH2Cl none of these Answer: C 11.28 M Which is the product of the reaction of one mole of HCl with one mole of CH3─CH2─CCH? A. CH3─CH2─CH=CHCl B. CH3─CH=CH─CH2Cl C. CH3─CH2─C=CH2 | Cl D. CH3─CH2Cl + CHCH Answer: C 11.29 E The reaction of an alcohol and a carboxylic acid yields A. a hydrocarbon. B. an ester. C. an ether. D. an aldehyde. E. a ketone. Answer: B 11.30 E The reaction of ethylene and water yields A. an aldehyde. B. an ester. C. an alcohol. D. an ether. E. an organic acid. Answer: C 11.31 M Oxidation of the secondary alcohol CH3CH(OH)CH3 will produce a/an A. aldehyde. B. amine. C. alkene. D. ketone. E. carboxylic acid. Answer: D 11.32 M Esters are made from two classes of organic compounds. They are A. acids and bases. B. amines and alcohols. C. alcohols and acids. D. amines and alkenes. E. alkenes and bases. Answer: C 193 194 CHAPTER 11: ORGANIC CHEMISTRY 11.33 M Which choice gives the structures of the hydrolysis products of the following ester? O || CH3CHCH2─ C─ OCH2CH3 | CH3 A. CH3CH2 ─C─OH and CH3─ CHCH2OH || | O CH3 O || B. CH3CHCH2─ C─OH and CH3CH2OH | CH3 O || C. CH3CH─ CH2 ─ C─ OH and CH3OH | CH3 O || CH3CH─ CH2─ C─ Cl and CH3CH2OH | CH3 D. Answer: B 11.34 M The reaction of Cl2 with CH4 to produce methylchloride is an example of a/an A. B. C. D. reaction involving radicals. addition reaction. reduction reaction. ester hydrolysis. Answer: A 11.35 E What is the number of hydrogen atoms in the hydrocarbon pentane? A. 5 B. 8 Answer: D C. 10 D. 12 CHAPTER 11: ORGANIC CHEMISTRY 11.36 M Isobutane differs from butane in that the former A. B. C. D. E. has a higher molecular weight. has a different percentage composition. is not a saturated hydrocarbon. has a different empirical formula. has a different structural formula. Answer: E 11.37 E An example of an organic acid is A. B. C. D. Answer: B 11.38 M Which functional group confers acidic properties upon an organic substance? A. –CHO E. –COOH B. –CO C. –CN D. –NH2 Answer: E 11.39 E The group is characteristic of A. aldehydes. D. esters. B. ketones. E. acids. C. alcohols. Answer: A 195 196 CHAPTER 11: ORGANIC CHEMISTRY 11.40 E An amino acid must contain all of which of the following the elements? A. C, H, O C. C, H, N, O B. C, H, N D. C, H, O, N, S Answer: C 11.41 M Which has the highest boiling point? A. n–butane C4H10 B. n–heptane C7H16 C. n–hexane C6H14 D. n–pentane C5H12 Answer: B 11.42 M A product of a reaction between an alcohol and a carboxylic acid is A. an aldehyde. C. an ether. B. a ketone. D. an ester. Answer: D 11.43 M The reaction between acetic acid and ethyl alcohol CH3COOH + C2 H5OH CH3COOC2 H5 + H2O is classified as A. saponification. C. esterification. B. addition. D. hydrolysis. Answer: C CHAPTER 11: ORGANIC CHEMISTRY 11.44 M The organic product of the chemical reaction shown below is : H H H Br2 + FeBr3 catalyst H H H A. B. H H Br H H H H Br Br Br Br H H H H H C. D. H H H H Answer: C Br H H H Br H H Br Br Br Br Br H H Br H 197 198 CHAPTER 11: ORGANIC CHEMISTRY 11.45 E Which of the following compounds contains one chiral carbon atom? A. Cl O | || CH3 ─ C ─ C ─ CH3 | Cl C. Cl | CH3 ─ O ─ C ─ O ─ CH3 | Br E. B. Cl | CH3 ─ CH2 ─ CH ─ CH3 D. O || CH3 ─ C ─ O ─ CH2 ─ CH3 O || CH3 ─ CH2 ─ C ─ H Answer: B 11.46 E Which of the following compounds contains one chiral carbon atom? CH3 OH CH3 | | | CH3 ─ C ─ CH2 ─ CH2 ─ CH ─ CH2 ─ C ─ CH3 | | Cl Cl A. H B. H CH3 H H H C. CH3Cl D. O || CH3 ─ C ─ CH3 E. O || CH3 ─ CH2 ─ C ─ OH Answer: A CHAPTER 11: ORGANIC CHEMISTRY SHORT ANSWER QUESTIONS 11.47 M Which of the following are structural isomers? a. CH3─ CH2─ CH2─ CH2 ─ CH3 b. CH3 ─ CH ─ CH2─ CH3 | CH3 c. CH3 ─ CH ─ CH─ CH3 | | CH3 CH3 d. CH3 | CH3 ─ C ─ CH3 | CH3 e CH2 = CH ─ CH2 ─ CH2 ─ CH2 ─ CH3 Answer: a,b, and d 11.48 M Write the formula for the alcohol and the carboxylic acid from which the following ester was prepared. O || CH3 ─ (CH2)14 ─ C | O(CH2)9CH3 Myricyl palmitate (beeswax) Answer: CH3─(CH2)14─COOH, 11.49 M CH3─(CH2)9─ OH Write the formula for the alcohol and the carboxylic acid from which the following ester was prepared. O || CH3 ─ C | O ─ CH2 ─ CH3 Ethyl acetate (nail polish remover) Answer: CH3─COOH, CH3─CH2─OH 199 200 CHAPTER 11: ORGANIC CHEMISTRY 11.50 M Write the formula for the alcohol and the carboxylic acid from which the following ester was prepared. O || CH3 ─CH2─ C | O─CH2─CH─CH3 | CH3 Isobutyl propionate (rum flavor) Answer: CH3─CH2─COOH, 11.51 E Name the following compound: Answer: 2,3 - dimethylbutane 11.52 E Name the following compound: Answer: 2,2 - dimethylbutane CH3─CH─CH2─OH | CH3 CHAPTER 11: ORGANIC CHEMISTRY TRUE-FALSE QUESTIONS 11.53 M The systematic name for the hydrocarbon with the following structural formula is 1-ethyl-2-methylbutane. CH2─CH3 | CH3─CH2 ─ C─CH3 | CH3 Answer: F 11.54 M The systematic name for the compound with the following structural formula is 4,5-dimethyl-2-hexene. CH3 | CH3─CH─CH─CH3 | CH=CH ─ CH3 Answer: T 11.55 M The oxidation product of the alcohol CH3CH2CH2OH when using Cr2O72 oxidizing agent is: ─ as the O || CH3─C─CH3 Answer: F 11.56 M The reaction of HCl(g) with CH3─CH=CH2 will yield CH3CH2CH2Cl as the main product. Answer: F 11.57 M 11.58 E Cycloalkanes have the general formula CnH2n. Answer: T Two substances that are non-superimposable mirror images of each other are called enantiomers. Answer: T 201