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NOMENCLATURE VI This exercise covers the basics of organic nomenclature.

It is primarily based upon the IUPAC system (the names under IUPAC rules are called systematic names). In a few cases there are special names, these special names are the common names and, in general, were in use before the IUPAC system was developed. Steps I through VII are basic to all organic nomenclature and you should pay particular attention to these steps. Each new type of organic molecule simply adds one or two extra steps to these seven. Once you have mastered the first basic steps, the rest is much easier. BASICS I. Chains In most cases, the root of the name comes from the longest continuous chain (“straight chain”) of carbon atoms in the compound. A straight chain is one that can be traced from one end of the compound to the other with backtracking. Any carbon atoms not a part of this chain are parts of branches. The naming of the straight chain is based upon the number of carbon atoms. This root also serves for branches. No. of C's 1 2 3 4 5 Root meth (form) eth (acet) prop but pent No. of C's 6 7 8 9 10 Root hex hept oct non dec

Additional information must be added to the appropriate root to complete the name of the compound. The roots “form” and “acet” are used in special cases that will be discussed later. In general, these two roots are not true IUPAC. II. Suffixes Adding a suffix to the root indicates the type of compound. Each type of compound has its own unique suffix. For most hydrocarbons (compounds containing only carbon and hydrogen) the basic suffixes are: -ane -ene -yne alkane (Hydrocarbons with only single bonds) alkene (Hydrocarbons with a carbon-carbon double bond) alkyne (Hydrocarbons with a carbon-carbon triple bond)

Double bonds and triple bonds are examples of functional groups. The importance of functional groups presented later.

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may be in front of the name of the hydrocarbon portion of the molecule (common name). If the “straight chain” is in the form or a non-aromatic ring. © 2006 Sevagram Enterprises . the compound is a branched compound. combine the prefix cyclo with the root. Example Cyclobutane H2C H2C CH2 CH2 Cyclo compounds may occur as cis and trans isomers similar to those in the alkenes covered below. III. pick the one with the most substituents (branches). If there are no branches present sometimes. Example The following will appear in the next three examples. The longest chain that contains a functional group (see later) b. an n. Cyclo Compounds Cyclo compounds have a prefix. If there is more than one chain (branched) then look for: a. a non-aromatic ring will be considered any ring of carbon atoms that does not have alternating single and double bonds. The longest chain (greatest number of carbon atoms not in branches). For now. Branches If not all the carbon atoms are in a continuous chain. C C C C C C C C C C C C C Longest chain is in boldface 9 C's nonane If there are two chains of the same length.IIa.

Arrange the branches alphabetically. tri-. Numbers Number the longest chain from one end to the other with the following considerations: a. b. V. The name is finished by adding a -yl suffix to the root. Each get its own number even if it is identical to one already used. This does not alter the arrangement from part a. The lowest number goes to any functional group.). 5-ethyl-2. The lowest number(s) go to the branch(es) Example For the above example the numbering of the chain (boldface carbon atoms) would be: 1 2 3 4 5 6 7 8 9 Do not alter assigned numbers later. tetra-. there are three branches. Example In the above example this gives: a.IV.2-dimethylnonane etc. Example In the above example. If there is more than one of a particular type use a prefix also (di-. Name Branches The root for the name of a branch is determined in I above. three branches = three numbers Separate numbers from other numbers by commas and numbers are separated from letters by a dash. c. 2 methyl groups 1 ethyl group a. 2 methyl groups = dimethyl c. b. ethyl before methyl b. simply count the number of carbon atoms. branch must © 2006 Sevagram Enterprises . Indicate the position of each branch with a number from step IV.

© 2006 Sevagram Enterprises . and one or more halogens-F. Halides Similar rules apply to the alkyl halides (compounds of C. but for now assume that it is true. Special Names for Branches Certain branches have special names. In general. The halogens are treated exactly the same as branches. The following material extends this basic procedure to compounds containing various additional functional groups. (This will not always be true.) In nomenclature. Indicate the different halogens as: F Cl fluoro chloro Br I bromo iodo Nonsystematic names for alkyl halides assume that the hydrocarbon portion of the molecule is a branch upon a halide ion. VII. Br. Example CH3 CH CH3 Cl This could be: 2-chloropropane (systematic) or isopropyl chloride (nonsystematic) The preceding steps outline the basic procedures of organic nomenclature covered in this class. each of these functional groups will be more important than the preceding functional groups. H. or I). it is possible to draw these in many different ways. Cl. Some of these are: CH3 CH CH3 CH3 CH CH2 CH3 isopropyl CH3 CH2 CH CH3 secondary butyl (or sec-butyl) CH3 CH3 C CH3 isobutyl tertiary butyl (or tert-butyl) Note: Be careful on these.VI. numbering of a chain must give the most important functional group the lowest possible number.

Use a number to indicate the position of the double bond (lowest possible).) C C C C 1-butene C C C (double bond between numbers 1 and 2) C 2-butene NOTE: C C C (double bond between numbers 2 and 3) C 1-butene (Not 3-butene) No numbers are necessary for the double bond in a simple cycloalkene as the double bond is always between carbon atoms 1 and 2. (Cycloalkanes may also have cis and trans isomers. and trans means on the opposite side. with the position of the double bond being indicated by the lowest numbered carbon atom of the double bond.4-octadiene (Note each double bond gets its own number) Alkenes may form geometric isomers.) © 2006 Sevagram Enterprises . Once numbered do not renumber. The longest chain must contain the C=C (unless a more important functional group is present). Cis means on the same side.Alkenes Alkenes are hydrocarbons containing at least one carbon-carbon double bond. If there is more than one C=C use a prefix on the -ene C C C C C C C C 1. There are two general types of geometric isomers: cis and trans.) Be careful not to mistake an aromatic substance for a cycloalkene. Example (Hydrogens left out for simplicity-not an acceptable final answer on an exam. (Numbers would be needed for all double bonds if more than one is present. The name will end in an -ene.

One alkene has a special (common) name: CH2=CH2 (ethylene). There are special names such as this one to learn in addition to the systematic names (ethene in this case).) H H C H H C H C H C H H trans-2-butene (The methyl groups (or hydrogen atoms) are across the double bond from each other. (H’s always cis and trans) H C H H C H C H H C H H C H H C C H H H C H H 2-butene H cis-2-butene (The methyl groups (or hydrogen atoms) are on the same side of the double bond. © 2006 Sevagram Enterprises .1-butene–no cis or trans isomers.) Make sure that only groups directly attached to the doubled bonded carbon atoms are use to determine if a molecule is cis or trans. if a molecule is not drawn to indicate whether it is cis or trans. it is not necessary to specify which it is. In addition.

2-dibromobenzene 1. they are: 1. The simplest aromatic presented here is benzene (C6H6). There are no cis/trans isomers for alkynes. Do not to forget to number around the ring to give the smallest numbers. Thus naming benzene derivatives is similar to the nomenclature discussed above.4-dibromobenzene You should draw each of these and prove to yourself that there are no others. If two or more of the hydrogens is replaced each of the replacements needs to have its position indicated by a number (even though one of the numbers must be a one). The common names use words (or letters) in place of the numbers. In many cases. For this class an aromatic ring will be indicated by a ring of six carbon atoms connected by alternating single and double bonds (resonating) or a six membered ring with a circle in it. Other compounds form by replacing one or more of the hydrogens.Alkynes Alkynes are hydrocarbons containing a carbon-carbon triple bond. but only such materials will be a part of this discussion. If. Benzene has six carbons in a ring each carbon has a single hydrogen. Thus replacing two of the hydrogens of benzene with bromines gives the formula C6H4Br2. Alkynes follow the same rules as alkenes except that the ending is -yne. There are three isomers with this formula. Aromatic compounds are not limited to six membered rings.3-dibromobenzene 1. for example. replacing one of the hydrogens with chlorine the compound becomes chlorobenzene (the carbon to which the chlorine is attached is automatically number one so no number is needed in the name). Aromatics Aromatic compounds contain one or more aromatic rings. Example 1-chloro-2-butyne CH3 C C CH2 Cl There is one special name: acetylene (C2H2). it is possible to use common names for the disubstituted aromatics. the IUPAC names are the same as the common names. In most of the cases examined here. The above three dibromobenzenes have the following common names: ortho-dibromobenzene meta-dibromobenzene para-dibromobenzene o-dibromobenzene m-dibromobenzene p-dibromobenzene © 2006 Sevagram Enterprises .

Either the name or the single letter abbreviation may be substituted for 1. Only functional groups containing oxygen and/or nitrogen will be considered at this time. branching on the methyl carbon (C6H5CH2-) gives a benzyl branch. Functional groups are normally the place where a molecule will react. Thus. The general formula for an alcohol is R-O-H There are two ways to name alcohols. for example. In some cases more than one R may be needed. The functional group normally gets the lowest number when numbering the chain. A benzene ring present as a branch is a phenyl group (C6H5-). Toluene forms by replacing a hydrogen from benzene with a methyl group (C6H5CH3). 1.3. For indicating the formulas of various derivatives. Nomenclature for toluene derivatives is similar to benzene derivatives. if this is the case they may be designated R and R’ etc. The only other aromatic hydrocarbon covered here is toluene. Derivatives Derivatives are organic compounds containing other elements in addition to carbon.or 1. when a hydrogen from one of the ring carbons (not from the methyl) is replaced by. it is common practice to use an R to indicate a hydrogen or hydrocarbon part of the molecule. In this case. The IUPAC system requires the final -e be removed from the name of the hydrocarbon and an -ol be put in its place. a bromine the following isomers could be formed (C6H4BrCH3): ortho-bromotoluene meta-bromotoluene para-bromotoluene 2-bromotoluene 3-bromotoluene 4-bromotoluene Changes on the methyl carbon of the toluene give a benz root. The carbon with this methyl group is automatically number one (this number one is not in the name).2-. For example. pronounce the entire name when naming the compound. the hydrocarbon portion is named as a branch on an alcohol. The benzene ring may be a branch. hydrogen and halogens. Note: Even when the single letter abbreviation is used. These other elements are part of functional groups. and it must be part of the longest chain (this is true even when another chain contains more carbon atoms). For the common name. remove one of the hydrogens and attach the ring to something else.4-. Oxygen Derivatives Alcohols Alcohols or organic compounds where one of the hydrogens has been replaced by a hydroxyl group. © 2006 Sevagram Enterprises .

etc. © 2006 Sevagram Enterprises . 3 = position of I Replacing one hydrogen on an aromatic ring with an OH gives a phenol.3-propandiol H H O C H H C H H C H O H The presence of other groups may complicate the numbering. (The alcohol is the most important group present.) 2 = double bond between C2 and C3. Example 1. so it gets the lowest number.) are necessary if more groups are present. there is no room for it in front of the prop. The simplest phenol is the compound phenol (C6H5OH). but they often behave differently. tri. This must be before the prop.Example 1-propanol H H C H H C H or n-propyl alcohol H C H O H Multiple numbers and prefixes (di. Phenols may look like alcohols. Example I C H C H 3-iodo-2-propen-1-ol H C H O H 1 = position of alcohol group. If an -OH replaces one of the hydrogens on the methyl group of toluene the compound is benzyl alcohol. The carbon to which the hydroxyl group is attached in number 1.

form. Example C6H5CH2CHO phenylethanal or phenylacetaldehyde © 2006 Sevagram Enterprises .are the preferred roots). Example Example Example CH3CH2-O-CH3 ethyl methyl ether (alphabetical) CH3CH2-O-CH2CH3 diethyl ether C6H5-O-CH2CH3 ethyl phenyl ether Carbonyl Derivatives These are oxygen-containing organics containing a carbonyl group. C O Carbonyl group Aldehydes Aldehydes have the general formula: R C H O R may also be an H.and acet. Aldehydes are named similar to alcohols except that an -al suffix is used in place of an -ol suffix. This gives the general formula: R-O-R'.Ethers Ethers are organic compounds where one oxygen is placed between two carbon atoms. When naming an ether both R and R’ are named as branches (-yl) suffix and separated placed before the word ether.) Common names use the suffix -aldehyde instead of -al (also. The carbonyl carbon must be number 1 so no number is needed. Example propanal H H C H H C H C H O (The carbonyl C must be number 1.

a minimum of three carbons are needed.) Carboxylic Acids The general formula for a carboxylic acid is: H O C R O (R may also be an H) The carbonyl C is automatically number 1. not two. Again. carbons are involved. as in aldehydes. There is one special name that you will need to know: CH3COCH3 propanone acetone (Note the acet.) Ketones Ketones have the general formula: R C R' O Thus. Special names and IUPAC names for the two simplest carboxylic acids are: HCOOH CH3COOH formic acid acetic acid methanoic acid ethanoic acid © 2006 Sevagram Enterprises .Three special names are important here: HCHO CH3CHO C6H5CHO formaldehyde acetaldehyde benzaldehyde methanal ethanal benzaldehyde (This is one of the cases where the systematic name is the common name. the carbonyl carbon receives the lowest number. Carboxylic acids are named like alcohols except that the suffix is -oic acid. Naming is the same as for alcohols except that an -one suffix is used.root even though three.

but not R) The naming of an ester relates to how an ester forms. In a condensation reaction. R'. In the general formula. R. © 2006 Sevagram Enterprises .Two other important carboxylic acids are benzoic acid (C6H5COOH) and oxalic acid (HOOCCOOH = H2C2O4). Example O H CH3 C O + H O CH3 O CH3 C O CH3 H + O H acetic acid ethanoic acid methyl alcohol methanol methyl acetate methyl ethanoate This is condensation reaction. The carboxylate ion is named by replacing the -ic acid with -ate. Esters form by the reaction of an acid and an alcohol. is from the alcohol (named as a branch). Example HCOOCH3COOEsters The general formula for an ester is: R O C R' O formate ion acetate ion methanoate ion ethanoate ion (R’ may be a hydrogen. The loss of the acidic hydrogen from an acid produces a carboxylate ion. and. splitting out a small molecule and joining two groups. is from the acid (named as a carboxylate ion).

Nitrogen Derivatives There are two major types of nitrogen derivatives: amines and amides. Amines Amines are ammonia derivatives just as alcohols are water derivatives. Example CH3CH2-NH2 CH3CH2-NH-CH3 ethylamine ethanamine ethylmethylamine (alphabetical) N-methylethanamine If a -NH2 group is attached to a larger molecule. this group is called an amino group. Amides The general formula for and amide is: R C R' N R" O (Any. A benzene ring with one of the hydrogens replaced by an amino group (C6H5NH2) is aniline. and it is not to be named as an amine. Amines are similar to alcohols or ethers except that N replaces O. Do not forget. Amides are similar to esters except that N replaces the noncarbonyl O. © 2006 Sevagram Enterprises . If one of the carbons. In the IUPAC system. Amide nomenclature is therefore similar to ester nomenclature. of the R’s may be hydrogen) Amides form in a method analogous to esters (even though the exact reaction will not work directly). label additional groups on the nitrogen with an N. IUPAC nomenclature uses an -amine suffix. or all. only the carbon atoms get numbers. from benzene is replaced by a nitrogen (C5H5N) pyridine forms. Indicate substituents on the nitrogen with an N. Naming amides is done by dropping the -oic acid (or -ic acid) from the name of the corresponding acid and replacing it with -amide. Pyridine is still aromatic and the nitrogen occupies position number 1. common nomenclature names all of the organic groups as branches. In these compounds replace one or more of the hydrogens by an organic group. and its attached hydrogen.

Example CH3 C N CH3 O H N-methylacetamide H C O N CH3 or N-methylethanamide CH3 N.N-dimethylformamide or N.N-dimethylmethanamide © 2006 Sevagram Enterprises .

2-methylbenzaldehyde 13. ethyl acetate 17. isopropyl alcohol 8. 4-phenyl-2-pentanol 9. Toluene © 2006 Sevagram Enterprises . 4-hexenoic acid 15.PRACTICE SET VI-1 Draw the structure of each of the following: (For additional practice do both the condensed and structural formulas) 1. 2-pentanone 14. 1-ethyl-3-methylcyclohexane 4. 1. tert-butyl phenyl ether 11. Dimethyl ethyl amine 18.3. 3-bromophenol 10. 1-chloro-2-butene 5. 5-methyl-1-hexyne 7. methyl propanate 19. 2-methylhexane 2. propanal 12. Benzene 20.5-dibromocyclohexene 6. potassium acetate 16. 2.4-trimethylpentane 3.

4-dimethyl-1-pentyne 6.5-trimethyl-4-propylheptane 3.PRACTICE SET VI-2 Draw the structure of each of the following: (For additional practice do both the condensed and structural formulas) 1. 3-phenyl-2-propen-1-ol 7. methyl p-chlorobenzoate 13. 4. 2.N-dimethylacetamide 15. N. 3-methyl-2-heptene 19. 2-hexene 17. 3-chloro-1-octene 5. isopropyl bromide 2. butanone 10.5-dimethylcyclohexene 9. 2-methylpropanal 11. 3. 3-chloropropyne 16. trans-2-pentene 18.3. diethyl ether 8. 3-ethyl-3-methylhexane © 2006 Sevagram Enterprises . 2-chloro-3-methylpentane 20. methanamine 14. 4-methylhexanoic acid 12. 2-methylcyclohexanol 4.

CH3-CH2-CH2-CH2-NH-CH3 15. CH3-CH2-CH=CH-CH3 8. CH3-CH2-CH2-CH2-CH2-COO19. CH3-CH2-CH2-COO-CH3 10. CH3-CH2-CH2-CH2-CH2-CO-NH-CH2-CH3 14. ClC6H4NH2 (3 names) 20. CH3-CO-CH3 13. CH3-CH2-CH2-C6H5 6. CH3-CH2-CH2-CH2-CH2-OH 2. CH3-CH2-CH3 17. CH3-C6H5 7. CH3-CH2-CH2-CH2-CH(CH3-CH2)-CH2-CH2-CH2-CHO 18. CH3-O-CH(CH3)2 16. CH3 CH3 CH2 CH CH2 CH CH2 CH2 CH2 CH3 CH2 CH3 4. CH3-CH2-CH2-CH2-CH2-O-CH2-CH3 11. C6H5OH 9. CH3-CH2-CH2-COOH 5.PRACTICE SET VI-3 Name each of the following: 1. CH3-CH=CH-CH2-CH2-OH © 2006 Sevagram Enterprises . CH3-CH2-CHO 3. CH3-CHBr-CHCl-CH2-CH3 12.

C5H12 2. C4H10O 6.PRACTICE SET VI-4 Draw and name each of the isomers of the following: 1. C4H8O2 9. C5H10O 8. C5H10 3. C5H8 4. C3H4Cl2 5. C4H11N 7. C4H9NO 10. C5H9O2Na (do only those containing a carbonyl group) (do only the acids and esters) (do only the amides) © 2006 Sevagram Enterprises .