Appendlces APPENDIX I SU BSTITUTIVE NOM ENCLATU RE OF ORGANIC COMPOUNDS The substitutive name of an organic compound is based on its principal group and principal chain T re principal group is assigned according to the following priorities o o o il tl ll C OH carborylic acid C O C C X anhydride il C OR ester o o o il o acid halide ll C NR2 amide C nitrile il C H aldehyde o ll C ketone TI rc principal chain OH alcohol phenol SH thiol NRz amine is identifiedby applying the following criteria in order until a decision can be made 1 Maximum number of substituents corresponding to the principal group 2 Maximum number of double and triple bonds considered together 3 Maximum length 4 Maximum number of substituents cited as prefixes A 1 A 2 APPE N Dtc ES A principal chain is numbered by applying the following criteria in order until there is no ambiguity Where multiple numbers are possible comparisons are made at the first point of difference l Lowest number for the principal group cited as a suffix that is the group on which the name is based 2 Lowest numbers for multiple bonds with double bonds having priority over triple bonds in case of ambiguity 3 Lowest numbers for other substituents taking into account the first point of difference rule p 62 rule 8 4 Lowest number for the substituent named as a prefix that is cited first in the name The name ts constructed starting with the hydrocarbon corresponding to the principal chain 1 Cite the principal group by its suffix and number its number is the last one cited in the name 2 lf there is no principal group name the compound as a substituted hydrocarbon 3 Cite the names and numbers of the other substituents in alphabetical order at the begin ning of the name These lists cover most of the cases cited in the text See Study Problems 8 1 8 3 pp 328 331 for illustrations For a more complete discussion of nomenclature see Nomenclature of Organic Chemistry 1979 Edition by the International Union of Pure and Applied Chemistry published by Pergamon Press In 1993 the IUPAC released A Guide to IUPAC Nomenclature of Organic Compounds Recommendations 1993 by R Panico W H Powell and Jean Claude Richer senior editor Blackwell Science This publication advocated one major change that affects the nomenclature of relatively simple compounds This change involves the way that principal groups are cited The 1993 Recommendations cite the principal group or multiple bond position with a number preceding the suffix itself whereas the 1979 Recommendarlons followed in this text cite the principal group or multiple bond position with a number preceding the hydrocarbon name These differences are best illustrated by example H C CHCH2CHTCH 3 1 97 9 1 99 Recornrtendatio ns 3 Recornntendations HOCH2CH2CH2CH2CHT HOCH2CH2CH2CH CH pentene 1 pentanol 4 penten l ol pent l ene pentan l ol pent 4 en l ol I The 1993 Recommendationshave not yet been generally adopted Thus names that adhere to either set of recommendations are acceptable APPENDIX II INFRARED ABSORPTIONS OF ORGANIC COMPOUNDS This table presents a summary of the important infrared absorptions discussed in this text For more detailed tables the reader may wish to consult more specialized texts such as Infrared Absorption spectroscopy by Koji Nakanishi and Philippa H Solomon San Francisco Holden Day 1977 or Organic Structure Analysis by Philip Crews Jaime Rodriguez and Marcel Jaspars 1998 Oxford University Press Chapter 8 APPENDIX II INFRARED ABSORPTIONS OF ORGANIC Typeofabsorption FrEquency Gm r lntensity COMPOUNDS A 3 Comment Alkanes stretch C H 2850 3000 m occurs in all compounds with aliphatic C H bonds C O bonds Alkenes C C stretch t CH CHz C 640 m 16ss m CHr 1660 1025 others C H stretch C H bend w not observed if alkene is symmetrical 3000 31 00 m 910 990 CH CHz s C CH 8e0 C C 960 980 s 675 730 s C C 800 8a0 s s H HH r f L L H position is highly variable Alcohols and Phenols O H stretch C O stretch 3200 3400 s 1050 1 250 s also present in other compounds with ethers esters etc Alkynes C C stretch C H 2100 2200 3300 stretch m not present or weak in many internal alkynes present in 1 alkynes only s Aromatic Compounds rh 500 t 600 s C C stretch 1 C H bend 650 750 strong m s 1660 2000 w overtone s two absorptions medium w weak Table continues A 4 APPENDTcES Type of absorption Frequency cm l lntensity Comment Aldehydes C O stretch ordinary a p unsaturated benzaldehydes C H 1720 1725 s 1680 1690 s 1700 s zz20 m stretch Kctones C O stretch s ordinary 1710 171 5 d unsaturatd ketones l67G 168O s 1680 1690 s aryl increases with decreasing ring size Table 2t 3 p 996 Carborylic Acids C O stretch ordinary t 710 s benzoic 1680 1690 s 2400 3000 s O H acids stretch very broad Esterc and Lactonet C O stretch 1735 1745 s increases with decreasing ring size Table 21 3 p 996 Acid Chlorides C O stretch 1800 s a second weaker band sometimes observed r at 700 1 750 Anhydrides C O stretch two bands increases with decreasing ring size 1760 1820 s in cyclic anhydrides Amldesand Lactams C O stretch 165G1655 s increases with decreasing ring size Table 21 3 p 996 N H bend 1640 N H 3200 3400 m stretch s doublet absorption observed for some primary amides Nitriles C N stretch 2200 2250 m stretch 3200 337s m Amines N H s strong m medium w weak several absorptions sometimes observed especially for primary amines APPENDIX III PROTON NMR CHEMICAL SHIFTS IN ORGANIC COMPOUNDS A 5 APPENDIX III PROTON NMR CHEMICAL SHIFTS IN ORGANIC COMPOUNDS This appendix is subdivided into a table of chemical shifts for protons that are pa rt of functtonal groups and a table of chemical shifts for protons that are adjacenfto functional groups A Protons within Functional Groups Chemical shift ppm Group tl C C H tl r a 0 4 7 1 5 ll c H 9 1 1 o H O H Chemical shift ppm Group tl 4 6 5 7 C N H 7 s 9 5 I varies with solvent and with acidity of O H c NH 0 s 1 5 I c c H Y V 1 7 2 s GNH 6 5 8 5 2 s 3 s B Protons Adjacent to Functional Groups In this table a range of chemical shifts is given for protons in the general environment I H C G in which G is a group listed in column 1 and the two other bonds are to carbon or hydrogen The remaining columns give the approximate chemical shifts for methyl protons H3C G methylene protons CH2 G and methine protons CH G respectively The shifts in the following table are typical some variation with structure of a few tenths of a ppm can be expected The chemical shifts …