A-6 APPENDⅨX1 TABLE D Selected Physical Properties of Representative Aldehydes and Ketones(Continued) Compound Melting Solubili Structural formula Ketones Acetone CHaCCH 94.8 2-Butanone CH3 CCH2 CH3 86.9 2-Pentanone CH3 CH3 778 102.4 3-Pentanone CHaCH2 CH 399 1020 4.7 Cyclopentanone -51.3 43.3 45 155 Acetophenone C6HsCCH3 202 Insoluble Benzophenone CeHsCCsH Insoluble TABLE E Selected Physical Properties of Representative Carboxylic Acids and Dicarboxylic Acids Structural Melting point,° Solubili formula point, (1 atm) g/100 mL H2O Carboxylic acids Formic acid HCO,H 8.4 101 Acetic acid CH3CO2H 16.6 118 Propanoic acid CH3CH2 CO2H 20.8 141 Butanoic acid CH3CH2 CH2CO2H Pentanoic acid CH3(CH2)3CO2H 34.5 186 33(16° Decanoic acid CHa(CH2)CO,H 31.4 0.003(15° HcO 1224 250 021(17° Dicarboxylic acids Oxalic acid HO2CCO2H Sublimes 10(20° Malonic acid HO2CCH2CO2H 130-135 Decompose 138(16 Succinic acid HO2CCH2 CH2CO2H 189 235 68(20° Glutaric acid HO2 CCH2 CH2 CH2CO2H 97.5 639(20° Forward Main Menu TOC Study Guide Toc Student OLCMHHE Website
A-6 APPENDIX 1 Compound name Ketones Acetone 2-Butanone 2-Pentanone 3-Pentanone Cyclopentanone Cyclohexanone Acetophenone Benzophenone Melting point, °C 94.8 86.9 77.8 39.9 51.3 45 21 48 Boiling point, °C (1 atm) 56.2 79.6 102.4 102.0 130.7 155 202 306 Solubility, g/100 mL H2O 37 Slight 4.7 43.3 Insoluble Insoluble Structural formula CH3CCH3 X O CH3CCH2CH3 X O CH3CCH2CH2CH3 X O CH3CH2CCH2CH3 X O C6H5CCH3 X O C6H5CC6H5 X O O O TABLE D Selected Physical Properties of Representative Aldehydes and Ketones (Continued) Carboxylic acids Dicarboxylic acids Compound name Formic acid Acetic acid Propanoic acid Butanoic acid Pentanoic acid Decanoic acid Benzoic acid Oxalic acid Malonic acid Succinic acid Glutaric acid Melting point, °C 8.4 16.6 20.8 5.5 34.5 31.4 122.4 186 130–135 189 97.5 Boiling point, °C (1 atm) 101 118 141 164 186 269 250 Sublimes Decomposes 235 Solubility, g/100 mL H2O 3.3 (16°C) 0.003 (15°C) 0.21 (17°C) 10 (20°C) 138 (16°C) 6.8 (20°C) 63.9 (20°C) Structural formula HCO2H CH3CO2H CH3CH2CO2H CH3CH2CH2CO2H CH3(CH2)3CO2H CH3(CH2)8CO2H C6H5CO2H HO2CCO2H HO2CCH2CO2H HO2CCH2CH2CO2H HO2CCH2CH2CH2CO2H TABLE E Selected Physical Properties of Representative Carboxylic Acids and Dicarboxylic Acids
APPENDIX 1 TABLE F Selected pht Properties of Representative Amines Alkylamines Struct Compound name g/100 mL H2O -92.5 Very high Ethylamine CH3 CH2NH2 16.6 CH3CH2 CH2 CH2 NH2 77.8 Isobutylamine sec-Butylamine tert-Butylamine CH3)3CNH 67.5 45.2 amine CH3(CH2)5NH2 Slightly soluble Cyclohexylamine 134.5 CsHsCH2NH 184.5 Secondary amines Dimethylamine (CH3)2NH 55.5 Very soluble soluble N-Methylpropylamine 62 Piperidine 106.4 Tertiary amines CHeRN 117.1 Triethylamine (CH3 CH2)3N 114.7 N-Methylpiperidine H3 Forward Main Menu TOC Study Guide Toc Student OLCMHHE Website
APPENDIX 1 A-7 Melting point, °C 92.5 80.6 50 85 104 67.5 19 18 10 10.5 92.2 50 3 117.1 114.7 Boiling point, °C 6.7 16.6 77.8 68 66 45.2 129 134.5 184.5 106.4 6.9 55.5 62.4 107 2.9 89.4 Solubility, g/100 mL H2O Very high Slightly soluble Very soluble Very soluble Soluble 41 Compound name Alkylamines Methylamine Ethylamine Butylamine Isobutylamine sec-Butylamine tert-Butylamine Hexylamine Cyclohexylamine Benzylamine Piperidine Primary amines Dimethylamine Diethylamine N-Methylpropylamine Secondary amines N-Methylpiperidine Trimethylamine Triethylamine Tertiary amines Structural formula CH3NH2 CH3CH2NH2 CH3CH2CH2CH2NH2 (CH3)2CHCH2NH2 CH3CH2CHNH2 (CH3)3CNH2 CH3(CH2)5NH2 C6H5CH2NH2 NH2 W CH3 (CH3)2NH (CH3CH2)2NH CH3NHCH2CH2CH3 N H (CH3)3N (CH3CH2)3N N CH3 (Continued) TABLE F Selected Physical Properties of Representative Amines
A-8 APPENDⅨX1 TABLE F Selected Physical Properties of Representative Amines (Continued) Arylamines Melting point°C Prim Aniline -6.3 m-Toluidine p-Toluidine o-Chloroaniline m-Chloroanilin p-Chloroaniline O-Nitroaniline m-Nitroaniline Secondary amines N-Methylaniline 57 N-Ethylaniline 205 Tertiary amines N, N-Dimethylaniline 2.4 194 Triphenylamine 127 365 Forward Main Menu TOC Study Guide Toc Student OLCMHHE Website
A-8 APPENDIX 1 Melting point, °C 6.3 14.7 30.4 44 14 10 72.5 71.5 114 148 57 63 2.4 127 Boiling point, °C 184 200 203 200 209 230 232 284 306 332 196 205 194 365 Compound name Arylamines Aniline o-Toluidine m-Toluidine p-Toluidine o-Chloroaniline m-Chloroaniline p-Chloroaniline o-Nitroaniline m-Nitroaniline p-Nitroaniline Primary amines N-Methylaniline N-Ethylaniline Secondary amines N,N-Dimethylaniline Triphenylamine Tertiary amines TABLE F Selected Physical Properties of Representative Amines (Continued)
APPENDIX 2 ANSWERS TO IN-TEXT PROBLEMS Problems are of two types: in-text problems that appear within the body of each chapter, and end of-chapter problems. This appendix gives brief answers to all the in-text problems. More detailed discussions of in-text problems as well as detailed solutions to all the end-of-chapter problems are provided in a separate Study Guide and Student Solutions Manual. Answers to part(a) of those in-text problems with multiple parts have been provided in the form of a sample solution within ach chapter and are not repeated here. CHAPTER 1 1.2 All the third-row elements have a neon core containing 10 electrons(1s22s2p6).The ele ments in the third row, their atomic numbers Z, and their electron configurations beyond the neon core are nad(Z=113s;Mg(Z=12)32;A(Z=13)323p1;S(z=14)323p3py;P(=15) 3233p23p2;S(z=16)3s23p2323p2;Cl(z=17)3s23p23p23p2;Ar(z=18) 323p23p232 1.3 Those ions that possess a noble gas electron configuration are(a)K;(c)H;(e)F; and 1.4 Electron configuration of C+ is 1522322p'; electron configuration of C- is 1322322p.Nei rC nor C possesses a noble gas electron configuration 1.5H:F HH 1.6H:C:C:H HH H H 1.8 Carbon bears a partial positive charge in CH3 Cl. It is partially negative in both CH4 and CH3Li, but the degree of negative charge is greater in CH3Li 1.9 (b) Sulfur has a formal charge of +2 in the lewis struct sulfuric acid. the two oxygens bonded only to sulfur each have a formal charge of -l, and the oxygens and hydrogens of the two OH groups have no formal charge;(c)none of the atoms have a formal charge in the Lewis structure given for nitrous acid 1.10 The electron counts of nitrogen in ammonium ion and boron in borohydride ion are both 4 Chalf of 8 electrons in covalent bonds). Since a neutral nitrogen has 5 electrons in its valence shell an electron count of 4 gives it a formal charge of +1. a neutral boron has 3 valence electrons, so lat an electron count of 4 in borohydride ion corresponds to a formal charge of -1 A-9 Forward Main Menu TOC Study Guide Toc Student OLCMHHE Website
APPENDIX 2 ANSWERS TO IN-TEXT PROBLEMS A-9 Problems are of two types: in-text problems that appear within the body of each chapter, and endof-chapter problems. This appendix gives brief answers to all the in-text problems. More detailed discussions of in-text problems as well as detailed solutions to all the end-of-chapter problems are provided in a separate Study Guide and Student Solutions Manual. Answers to part (a) of those in-text problems with multiple parts have been provided in the form of a sample solution within each chapter and are not repeated here. CHAPTER 1 1.1 4 1.2 All the third-row elements have a neon core containing 10 electrons (1s 2 2s 2 2p6 ). The elements in the third row, their atomic numbers Z, and their electron configurations beyond the neon core are Na(Z 11)3s 1 ; Mg(Z 12)3s 2 ; Al(Z 13) 3s 2 3px 1 ; Si(Z 14) 3s 2 3px 1 3py 1 ; P (Z 15) 3s 2 3px 1 3py 1 3pz 1 ; S (Z 16) 3s 2 3px 2 3py 1 3pz 1 ; Cl (Z 17) 3s 2 3px 2 3py 2 3pz 1 ; Ar (Z 18) 3s 2 3px 2 3py 2 3pz 2 . 1.3 Those ions that possess a noble gas electron configuration are (a) K; (c) H; (e) F; and (f) Ca2. 1.4 Electron configuration of C is 1s 2 2s 2 2p1 ; electron configuration of C is 1s 2 2s 2 2p3 . Neither C nor C possesses a noble gas electron configuration. 1.5 1.6 1.7 (b) (c) 1.8 Carbon bears a partial positive charge in CH3Cl. It is partially negative in both CH4 and CH3Li, but the degree of negative charge is greater in CH3Li. 1.9 (b) Sulfur has a formal charge of 2 in the Lewis structure given for sulfuric acid, the two oxygens bonded only to sulfur each have a formal charge of 1, and the oxygens and hydrogens of the two OH groups have no formal charge; (c) none of the atoms have a formal charge in the Lewis structure given for nitrous acid. 1.10 The electron counts of nitrogen in ammonium ion and boron in borohydride ion are both 4 (half of 8 electrons in covalent bonds). Since a neutral nitrogen has 5 electrons in its valence shell, an electron count of 4 gives it a formal charge of 1. A neutral boron has 3 valence electrons, so that an electron count of 4 in borohydride ion corresponds to a formal charge of 1. H C H H C C N F F C C F F H C H H H H H C H F
A-10 APPENDIX 2 1116H-NH3+6H-BH3 H HH 112(b)H—C C-H (c): Cl-C-C-Cl: (d)H-C-C--Cl HH H C-Hf)H—C (b)(CH3)2CHCH(CH,)2 (c)HOCH_ CHCH(CH3) (d)C CH—C(CH3)3 CH3 CH,--CH 114H一N一C-0-H 1.15(b)CH3 CH, CH,OH,(CH3)2CHOH, and CH3CH2OCH3(c)There are seven isomers of CaHioO. Four have -OH groups: CH3 CH,CH, CH,OH,(CH3)2CHCH2OH,(CH3)3COH, and CH3 CHCH2CH3. Three have C-O-C units: CH3 OCH, CH2CH, CH3 CH,, CH3, and (CH3)2CHOCH3 ←>:0 Forward Main Menu TOC Study Guide Toc Student OLCMHHE Website
A-10 APPENDIX 2 1.11 1.12 (b) (c) (d) (e) (f) 1.13 (b) (CH3)2CHCH(CH3)2 (c) (d) 1.14 1.15 (b) CH3CH2CH2OH, (CH3)2CHOH, and CH3CH2OCH3. (c) There are seven isomers of C4H10O. Four have ±OH groups: CH3CH2CH2CH2OH, (CH3)2CHCH2OH, (CH3)3COH, and . Three have C±O±C units: CH3OCH2CH2CH3, CH3CH2OCH2CH3, and (CH3)2CHOCH3 1.16 (b) (c) and C O O O C O O O C O O O C O O O C O H O O H C O O O CH3CHCH2CH3 OH H N H C O O H CH2 CH CH2 CH2 CH2 CH2 C(CH3) HOCH2CHCH(CH3 3 )2 CH3 H C H H C H C H O H C H H H C C H H N H C H H C H H H C H H C H Cl Cl C H Cl H H C H H H C C H Cl HHH H H C H C H H N H H H H B H H H H