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CHAPTER 24- Practice Exercise A. Kweyete Organic Chemistry 1. Which of the following is (are) a saturated hydrocarbon? (underline your choice) alkane alkyne alkene cycloalkane cycloalkene aromatic hydrocarbon 2. Identify the following general formulas as alkanes, alkenes, alkynes, and cycloalkanes. CnHn CnH2n CnH2n+2 CnH2n-2 Alkyne alkenes, cycloalkanes alkanes (cycloalkenes), alkynes, (diene) 3. Which one of the following is (are) an alkene with a carbon-carbon double bond? C4H10 C6H14 C4H8 CH4 C6H10 C2H2 C5H10 C2H2 C6H6 4. How many carbon atoms are in each of the following contain? Butane Octane Nonane Propyne 4 8 9 3 5. Write the IUPAC name for each of the following structure. Acetylene 2 cycolpentane 5 CH3 (a) CH3 - CH - CH2 - CH - CH2 - CH3 CH3 (d) (b) CH2 - CH2 - CH - C (CH3)2 - CH3 CH3 C -H CH3 CH3 - CH - CH2 - CH3 CH3 - CH2 - CH - CH3 (e) CH3 - CH - CH2 - C = CH2 Br CH3 CH3 CH3 CH3 Br (g) (c) H - C (h) CH3 Cl .a) 2,4-dimethylhexane .b) 2,2,3-trimethylhexane .c) ethyne .d) 3,4-dimethylhexane .e) 2,4-dimethyl-1-pentene .f) 2-pentene .g) 1-bromo,2-methyl-benzene .h) cis-1-bromo-4-chloro-cis-2,3-dimethylcyclohexane 1 (f) CH3 - CH2 - CH = CH - CH3 6. Write the condensed structures for the following compounds. (a) 3, 3, 4- trimethylheptane CH3CH2C(CH3)2CH(CH3)(CH2)2CH3 (b) 2, 3- dimethylbutane CH3CH(CH3)CH(CH3)2 (c) 1, 3- dibromopentane CH2BrCH2CHBrCH2CH3 . (d) 3, 4- dimethylhexane CH3CH2CH(CH3)CH(CH3)CH2CH3 (e) cis- 2, 3- dichloro-2-butene cis-CH3CCl=CClCH3 (f) trans- 1, 2- dibromocyclobutane trans-C4H6(Br)2 . (g) 4- ethyl- 3, 3- dimethylheptane CH3CH2C(CH3)2CH(C2H5)(CH2)2CH3 (h) p- xylene p-(CH3)C6H4(CH3) (i) m – chlorobenzoic acid m-ClC6H4COOH (j) Diethyl ether CH3CH2OCH2CH3 . (k) 3 - nitrophenol m-(NO2)C6H4OH (l) cyclobutylcyclopentane C5H9(C4H7) 7. Which class of functional group do the following belong to? O (a) OH alcohol___ (b) CHO aldehyde___ (c) C - H _aldehyde (e) CO carbonyl ( f) NH2 ( g) O amine O (d) C OH carboxylic acid (i) COO ether esther 8. Complete the following sentences: (a) The term hydrocarbon is used to denote compounds that contain carbon & hydrogen, only. (b) Pentane and isopentane are what type of isomer? ( structural, geometrical ) (c) Dichlorobenzene has 3 aromatic isomers. (ortho, meta, para isomers) (d) Cyclohexene has 2 hydrogen less than cyclohexane. (e) Alcohols have higher boiling point due to hydrogen bonding. 9. Match the following general formulas. (a) R - OH (b) R - CHO (c) R - COOH (e) ( I ) Ether (d) ( V ) Ketone (f) ( III) Ester (g) (VII) Amine (d) R - CO – R (e) R - O - R (b) ( II ) Aldehyde (f) R - COOR (g) R - NH - R (a) ( VI) Alcohol (c) ( IV) Carboxylic acid 10. Which of the following compounds does contain a carbonyl group? Please circle. I. Aldehyde II. Alcohol III. Ketone IV. Ether V. Ester VI. Amine VII. Amide 2 VII.Carboxylic acid 11.Identify(classify) the following oxygen-containing compounds as ketone, aldehyde, ether, ……… O a) CH3-CH2 - COOH b) CH3 - CO - CH3 O - CH3 e) c) OH H - C - CH2 - CH3 d) CH 3 - CH - CH3 CH3 f) CH - O - CH2 - CH3 g) CH3 - CO - NH - CH3 CH3 (a) (b) (c) (d) (e) (f) (g) carboxylic acid ketone aldehyde alcohol ether ether amide 12. Name the following alcohols. a) CH3 - CH2 - CH2 - CH2OH b) CH3 - CH2 - CH - CH3 OH d) CH2 - CH2 OH a) b) c) d) e) f) g) e) c) CH3 - COH - CH2 - CH3 OH CH3 CH3 f) CH3 - CHOH - CH3 g) CH3 - C - CH2OH CH3 OH butanols 2-butanol 2-methyl-2-butanol Ethylene glycol Phenol 2-propanol (OR Isopropyl alcohol) 2,2-dimethyl propanol 3 13. Name the following alkyl groups. a) CH3- b) CH3 - CH2- c) CH3 - CH2 - CH2- d) CH3 - CH - e) CH3 - CH2 - CH2 - CH2 - CH3 CH3 f) CH3 - CH - CH2 - g) CH3 - CH2 - CHCH3 CH3 a) b) c) d) e) f) g) h) i) j) h) CH3 - C - CH2 i) j) CH3 methyl ethyl propyl isopropyl n-butyl isobutyl secondary butyl tertiary butyl phenyl benzyl 14. How many structural isomers do the following compounds have? C3H8 1 C4H10 2 C5H12 3 C6H14 5 C4H9Cl 4 C3H5Br 4 15. Identify the following pairs as structural isomers, geometrical isomers, alike, or non-isomers. I. II. CH3 - CH2 - CH2 - CH - CH3 and and CH3 - CH - CH2 - CH2 - CH3 CH3 Br III. Br and IV. Br V. and Br CH2 - CH2 - CH2 - CH2 - CH- CH3 CH3 and CH2 - CH3 CH2 - CH2 - CH2 - CH2 - CH- CH3 I. structural isomers II. alike III. geometrical isomers***** IV. structural isomers V. non-isomers 4 CH3 16. What is the product of the following reactions. HBr b) CH3 - CH = CH -CH3 a) CH3 - CH2 - CH = CH2 c) CH3 - CH(CH3) - CH3 ether Br2 / light d) + Br2 H2 / Pd(C) or Ni(s) e) C3H8 + O2 g) Br2 /CCl4 H+ f) CH3 -OH + CH3 - COOH OH FeBr3 h) + CH3OH H+ COOH OH i) + CH3COOH CHOOH j) k) C17H35COO CH2CH3 + NaOH + CH3CH2Cl l) CH3CH2OH + CH3CH2OH a) CH3-CH2-CHBr-CH3 b) CH3-CHBr-CHBr-CH3 c) CH3-CBr(CH3)-CH3 d) e) 3CO2 + 4H2O O ║ f) CH3-O-C- CH3 g) 5 AlCl3 H+ h) O ║ C-OCH3 OH i) j) k) C17H35COONa + C2H5OH l) CH3-CH2-O-CH2-CH3 . 6 7