APPENDIX I.OF ORGANICAppendlcesSU BSTITUTIVE NOM ENCLATU RECOMPOUNDSThe substitutive name of an organic compound is based on its principal group and principalchain.T\re principal group is assigned according to the following priorities:oilotloil-C-X (acid halide) >olloil-C-OH (carborylic acid) > -C-O-C- (anhydride) > -C-OR (ester)oiloll-C-NR2 (amide) > -C-$ (nitrile) > -C-H (aldehyde) >oll-C- (ketone) > -OH (alcohol, phenol) > -SH (thiol) > -NRz (amine)TI.rc principal chain is identifiedby applying the following criteria in order until a decisioncan be made.1. Maximum number of substituents corresponding to the principal group2. Maximum number of double and triple bonds considered together3. Maximum length4. Maximum number of substituents cited as prefixesA-1A,-2 APPE N Dtc ES1 97 9 Recornrtendatio ns :1 99 3 Recornntendations:A principal chain is numbered by applying the following criteria in order until there is noambiguity. Where multiple numbers are possible, comparisons are made at the first point ofdifference.l. Lowest number for the principal group cited as a suffix-that is, the group on which thename is based2. Lowest numbers for multiple bonds, with double bonds having priority over triple bondsin case of ambiguity3. 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 nameThe name ts constructed starting with the hydrocarbon corresponding to the principalchain.1. Cite the principal group by its suffix and number; its number is the last one cited in thename.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 Nomen-clature of Organic Chemistry, 1979 Edition, by the International Union of Pure and AppliedChemistry, published by Pergamon Press.In 1993, the IUPAC released A Guide to IUPAC Nomenclature of Organic CompoundsRecommendations 1993, by R. Panico, W. H. Powell, and Jean-Claude Richer (senior editor),Blackwell Science. This publication advocated one major change that affects the nomencla-ture of relatively simple compounds. This change involves the way that principal groups arecited. The 1993 Recommendations cite the principal group or multiple bond position with anumber 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 hydrocarbonname. These differences are best illustrated by example.H:C-CHCH2CHTCH-3I -pentenepent- l -eneHOCH2CH2CH2CH2CHT1-pentanolpentan- l -olHOCH2CH2CH2CH:CH:4-penten- l -olpent-4-en- l -olThe 1993 Recommendationshave not yet been generally adopted. Thus, names that adhereto either set of recommendations are acceptable.APPENDIX II. INFRARED ABSORPTIONS OF ORGANIC COMPOUNDSThis table presents a summary of the important infrared absorptions discussed in this text. Formore detailed tables, the reader may wish to consult more specialized texts, such as InfraredAbsorption spectroscopy, by Koji Nakanishi and Philippa H. Solomon, San Francisco:Holden-Day, 1977; or Organic Structure Analysis, by Philip Crews, Jaime Rodriguez, andMarcel Jaspars, 1998, Oxford University Press, Chapter 8.APPENDIX II. INFRARED ABSORPTIONS OF ORGANIC COMPOUNDS A.3Typeofabsorption FrEquency,Gm-r(lntensity)* CommentAlkanesC-H stretch 2850-3000 (m) occurs in all compounds with aliphatic C-H bondsAlkenesC:C stretch-CH:CHzt 640 (m)16ss (m)C: CHr/others1660-1025 (w) not observed if alkene is symmetrical:C-H stretch3000-31 00 (m):C-H bend-CH:CHz910-990 (s)8e0 (s)C:CH,/960-980 (s)\/C:C/\HHH\/r-fL-L/\675-730 (s\ position is highly variable800-8a0 (s)H\/C:C/\Alcohols and PhenolsO-H stretch 3200-3400 (s)C-O stretch 1050-1 250 (s) also present in other compounds with C-O bonds:ethers, esters, etc.AlkynesC:C stretch 2100-2200 (m) not present or weak in many internal alkynes-C-H stretch3300 (s)present in 1-alkynes onlyAromatic CompoundsC:C stretch 1 500, t 600 (s) two absorptionsrhC-H bend650-750 (s)overtone1660-2000 (w)*(s) - strong; (m) - medium; (w) - weak.(Table continues)A-4 APPENDTcESType of absorption Frequency, cm-l (lntensity)* CommentAldehydesC:O stretchordinary 1720-1725 (s)a,p-unsaturated 1680-1690 (s)benzaldehydes 1700 (s)C-H stretchzz20 (m)KctonesC:O stretchordinary 1710-171 5 (s) increases with decreasing ring size (Table 2t .3,p.996)d,&unsaturatd l67G-168O (s)aryl ketones 1680-1690 (s)Carborylic AcidsC:O stretchordinaryt 710 (s)benzoic acids 1680-1690 (s)O-H stretch2400-3000 (s)very broadEsterc and LactonetC:O stretch 1735-1745 (s) increases with decreasing ring size (Table 21.3,p.996)Acid ChloridesC:O stretch1800 (s)a second weaker band sometimes observed atr 700-1 750C:O stretch1760,1820 (s)Amldesand LactamsC:O stretch 165G1655 (s) increases with decreasing ring size (Table 21.3,p.996)N-H bend 1640 (s)Anhydridestwo bands; increases with decreasing ring sizein cyclic anhydridesN-H stretch3200-3400 (m)doublet absorption observed for someprimary amidesNitrilesC-N stretch 2200-2250 (m)AminesN-H stretch3200-337s (m)several absorptions sometimes observed,especially for primary amines*(s) : strong; (m) : medium; (w) : weak.APPENDIX III. PROTON NMR CHEMICAL SHIFTS IN ORGANIC COMPOUNDS A-5APPENDIX III. PROTON NMR CHEMICAL SHIFTSIN ORGANIC COMPOUNDSThis appendix is subdivided into a table of chemical shifts for protons that are pa rt of functtonalgroups and a table of chemical shifts for protons that are adjacenfto functional groups.A. Protons within Functional GroupsGroupChemical shift, ppmGroupChemical shift, ppmtl-C-C-Htl4.7 -1 .50ll-c-H9-1 1H\/r-a\_-\-/\otl-C-N-HI7.s-9.54.6-5.7-O-H varies with solvent andwith acidity of O-H-c-c-H 1.7-2.s-c-NH-I0.s-1.5/Y*V6.5-8.5B. Protons Adjacent to Functional GroupsIn this table, a range of chemical shifts is given for protons in the general environmentIH-C-Gin 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