Basic Organic Nomenclature A series of three computer programs have been developed m t h Bnsir ~ language to give studenra practice in naming hranched alkanes, compounds with various functional groups, and henzen~derivatives. Each program prints a structure A short hrlp section iiolfered i f t h student ~ is incorrect. Hecan then try a ~ a i n and chrcks the name given hy t h ntudmt. ~ or can obtain the correct answer and try a new structure. The alkanes are generated at random by putting hydrogen, methyl, ethyl, and propyl groups on the 10 positions on butane. Structures of butane through 4,4,5,5,6,6,7,7octapropyldecane are possible with the exception that in the resulting structures branched suhstituents like iso-propyl are not allowed. Over one million apparently different structures are p s i b l e . The number of different compounds is less since many can appear in different orientations and with the long chain "bent" differently. The help section redraws the structure with the longest carbon chain straight and the carbons correctly numbered. The second program chooses at random from the following types of compounds
RX ROH ROR
alkyl halide X=F,Cl,Br,orI alcohol ether
RSH
thiol
RCHO
aldehyde RCONH2
amide
RNHz RCOOH
amine earboxylic acid
RCOR RCOOR
ketone ester
alkene alkyne
RCH==CHR R e R
The H groups are choien at random from a list of straight chain alkanes including methyl through heptyl. This choice is limited for ketone, alkenqand alkynm m a totalcarbon chain lenah not w a r 1O.Thrlpareatotal of l%mmpoundapm~ihle. The program lint ask* what type of compound has been printed and then asks the name of the compound. The help eetion lists the above table of types of compounds and gives rules for naming the pnnirulnr type of rompuund in question. The third programgenerates henwne derivatives by picking at random ~uhtiturnrsfromF. Hr,CI, I. NO,,CH:,, CH3CHg, and CHjCHKH? The odds vn,arammed arr 3 to I that rach of the six hvdroeens wdl not he rcolared.so the avrraae eornpound will have two substitum6. Over a half million apparently differeit str;ctures are possibie. ~ h e n u r n b eof r dyfferent compounds is less since each can appear in different orientations. The help section redraws the structure with the carbons eloekwiae. numbered atartine s t the too and - ~mine ~ ~ ~ . - - ~ IUPAC k e s are used throughout. Sample output and listings of these programs are available from the author. This work was supported by NSF Grant No. SED76-02103. ~~~
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Eastern Washington University Cheney, 99004
224 1 Journal of ChemicalEducation
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