General Strategy For Naming Simple Organic Compounds (Bare bones summary sheets)
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1 General Strategy For aming Simple rganic ompounds (Bare bones summary sheets). Find the highest priority group. These are listed in order of priority in the table of functional groups.. Find the longest chain containing the highest priority group. You should know carbon chains of length - (listed in the table).. umber the longest chain containing the highest priority group to give the highest priority group the lowest number possible in numbering the longest chain. For the first seven groups, the functional group carbon will be number (if it is the highest priority group) and the can be omitted, since it is understood that it has to be this way.. Usually the highest priority group is named as a suffix at the end of alkane, alk-#-ene or alk-#-yne. The final e is dropped if the suffix begins with a vowel and it is retained if the suffix begins with a consonant. A number will be present in front of the suffix name unless its position is unambiguously clear (i.e. carboxyl groups aldehydes, nitriles, et always =, if highest in priority). If there is a / pi functional group to identify (alkene or alkyne), the number in front of its part of the name describes its position (see rule below). If both a pi bond and a high priority substituent are present, then two numbers may be necessary, one for each functionality.. Lower priority groups are named with their prefix names and their location numbers based on the numbering of the parent chain (always true for substituents numbered on the next page). The lower priority substituents should be listed in alphabetical order. Some parts of prefix names count in this regard and some don't. We will not emphasize this aspect in this course.. Double bonds and triple bonds are named as alk-#-ene or alk-#-yne, respectively. If both are present, name as alk-#-en-#-yne. Multiple pi bonds (or other substituents) use the prefixes di, tri, tetra, penta et with a number for each occurrence. In such cases, an "a" is added in front of the numerical prefix for better phonetics. (alka-#,#-diene or alka-#,#,#-triyne, alka-#,#-dien-#,#-diyne, et) The essential functional groups to know (for our course) and their prefixes and suffixes are given in the attached table. In this table the term alkan-#-suffix is a generic term for any alkane with a functional group suffix, and it must be replaced with the correct parent stem name based on the number of carbons in the longest chain ( - for us). If there is a double bond, the name will change to alk-#-en-#-suffix and if there is a triple bond, the name will change to alk-#-yn-#-suffix. S Z (Z,S)--ethoxy--methyl--oxooct--en--ynoic acid otice that no "" is used for the carboxylic acid group, because it has to be "" in this structure.
2 Functional Group. arboxylic acid prefix not considered suffix alkanoic acid. Anhydride. Ester. Acid halide. Amide. itrile ' l not considered not considered #-chlorocarbonyl #-carbamoyl #-cyano alkanoic anhydride (if symmetrical) alkyl alkanoate (') ( ) alkanoyl chloride alkanamide alkanenitrile The part of each name specific to the functional group is in bold and underlined to help you see those features. They are not part of the names. "" = carbon chains alkane alkyl # chain branch carbons name name. Aldehyde. Ketone. Alcohol 0. Thiol ' S #-oxo #-oxo (older = #-keto) #-hydroxy #-mercapto alkanal #-alkanone #-alkanol #-alkanethiol methane methyl ethane ethyl propane propyl butane butyl pentane pentyl hexane hexyl heptane heptyl octane octyl nonane nonyl 0 decane decyl undecane undecyl dodecane dodecyl. Amine #-amino #-alkylamine / #-alkanamine. Ether. alogen X ' #-alkoxy (if more than 's, then #-alkoxyl) (can also use "#-oxa" prefix and count as carbon in longest chain) #-fluoro, #-chloro, #-bromo, #-iodo. Azide* #-azido. Diazo* #-diazo always prefixes (no suffix names). itro* #-nitro. itroso #-nitroso. arbon branches #-alkyl, #-(alk-#-enyl), #-(alk-#-ynyl) * = formal charge is necessary in these Lewis structures and there are two reasonable resonance structures stereoisomerism prefixes parent stem / pi bonds high priority suffix /S and E/Z branches and see box low priority above functional groups -ene -yne see list above
3 n a separate piece of paper, provide acceptable names for the following structures. After you have named your structures, turn it around and redraw each structure by the name you gave it. learly number your longest chain in your drawing. ints are provided just below the structures and answers are provided just below the hints. Use a separate piece of paper to cover those up until you need them. Some additional nomenclature examples follow these, but are not entirely finished. omenclature Worksheet Points to onsider. What is the highest priority group present?. What is the longest chain with that group?. umber that chain (ring) so that the high priority group gets the lowest number.. Identify branches and other functionality with their numbers. (Usually named as prefixes.). ombine everything into one name with proper use of hyphens (between numbers and letters) and commas (between numbers and numbers).. amides. nitriles. aldehydes S. ketones
4 . alcohols d.. thiols S S S. amines and ethers lues are provided on the following pages.
5 amides prefix = carbamoyl suffix = -amide. amide. amine. nitro Do not count the nitrile carbon when it is a substituent.. amide. nitrile. amine. alkyne. ketone benzamide nitriles prefix = cyano suffix = -nitrile etain the final "e" because nitrile begins with a consonant. Make sure to count the nitrile carbon when it is the highest priority group.. nitrile. alcohol. nitro. alkene ' '. nitrile. alkene. alkyne. ketone benzonitrile aldehydes prefix = oxo suffix = -al. aldehyde. ether. alkene. alcohol S. aldehyde. thiol. alkyne. ketone benzaldehyde
6 ketones prefix = oxo suffix = -one. ketone. alkene. ketone. alkene. alkyne acetophenone or -phenyl--ethanone benzophenone alcohols prefix = hydroxy suffix = -ol. alcohol. alkene. ether. alcohol. alkyne. alkene benzyl alcohol d. phenol thiols prefix = mercapto suffix = -thiol S etain the final "e" because thiol begins with a consonant.. thiol. alkene. ether S ' ' '. thiol. alkyne. cycloalkenyl S
7 amines prefix = amino suffix = -amine. amine. alkyne ' '. amine. alkene. ether ethers prefix = alkoxy (methoxy, ethoxy, propoxy, et) suffix = none ' ' '. ether. aromatic ' Bonus Structure ' ' ' 0 ' ' ' ' ' ' (E,Z)--hydroxy--me t h ylhexa-,-dienyl (Z)--cyano--(-heptyl-,-dimethylcyclopent--enyl)- -mercapto-,-dioxo--nitro--butoxy--aminododec--en-0-ynoate S ' ' ' '' '' '' '' '' ' ' ' ' ' ' ' ''. ether. cycloalkene See if you can come up with the name given below on your own. are provided on the following pages.
8 amides prefix = none for our course suffix = -amide -amino--nitrobutanamide. amide. amine. nitro Do not count the nitrile carbon when it is a substituent. -cyano--(,,-dimethylamino)--oxohept--ynamide. amide. nitrile. amine. alkyne. ketone benzamide nitriles prefix = cyano suffix = -nitrile -hydroxy--nitropent--enenitrile ' ' -ethenyl--oxopent--ynenitrile etain the final "e" because nitrile begins with a consonant. Make sure to count the nitrile carbon when it is the highest priority group.. nitrile. alcohol. nitro. alkene. nitrile. alkene. alkyne. ketone benzonitrile aldehydes prefix = oxo suffix = -al -methoxy--hydroxyhept-z-enal Z. aldehyde. ether. alkene. alcohol S -mercapto--oxohept--ynal. aldehyde. thiol. alkyne. ketone benzaldehyde
9 ketones prefix = oxo suffix = -one -benzyl--phenyloct-e-en--one. ketone. alkene E oct-e-en--yn--one E. ketone. alkene. alkyne acetophenone or -phenylethan--one benzophenone alcohols prefix = hydroxy suffix = -ol -methoxyoct-z-en--yn--ol Z. alcohol. alkene. ether hept--en--yn--ol. alcohol. alkyne. alkene benzyl alcohol d. phenol thiols prefix = mercapto suffix = -thiol S -methoxyoct-z-ene--thiol etain the final "e" because thiol begins with a consonant.. thiol. alkene. ether S ' ' ' -(cycloprop--enyl)hept--yne--thiol. thiol. alkene. ether S -phenyl--propanethiol
10 amines prefix = amino suffix = -amine -methylhept--yn--amine. amine. alkyne ' ' -(-methylethyl)--methoxypent-z-e n--amine (can also use "-isopropyl") Z. amine. alkene. ether ethers prefix = alkyoxy suffix = none ' ' ' -(-methylpropoxy)--phenylbutane or isobutyl -phenylbutyl ether. ether. aromatic ' ' ' ' -butoxycyclohex--ene. ether. cycloalkene Bonus Structure 0 ' ' ' ' ' S ' ' ' ' ' ' ' ' ' ' (E,Z)--hydroxy--methylhexa-,-dienyl (Z)--cyano--(-heptyl-,-dimethylcyclopent--enyl)- -mercapto-,-dioxo--nitro--butoxy--aminododec--en-0-ynoate Some additional examples are provided below.
11 . Problems - alkanes ints 0 ' ' ' ' 0 ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' alkanes prefix = branch names end in "-yl" suffix = -ane 0 ' ' ' ',-dimethyl--ethyl--(-methylethyl)dodecane 0 ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' trans--(-methyl--ethylpentyl)--(-methylpropyl)cyclononane -cycloheptyl--(,-dimethylcyclohexyl)--(-methyl--ethylcyclopentyl)decane. Problems alkenes d. e. ints d. e. ' ' ' ' ' ' ' ' ' ' ' alkenes prefix = none suffix = -ene ' ' older current (E)--pentene or (E)-pent--ene E stereochemistry
12 older current (Z)--ethyl--methyl--heptene or (Z)--ethyl--methylhept--ene Z stereochemistry ' ' ' ' ' (E)--(cyclopent--enyl)hex--ene Z stereochemistry d. ' ' ' ' ' (E)--(prop-Z-enyl)cyclooct--ene E Z ' ' e. ' ' ' (E,Z)--propylocta-,-diene E Z. Problems - alkynes d. e. ints ' d. e. ' ' ' ' ' ' ' ' alkynes prefix = none suffix = -yne ' ' ' ' older current -pentyne or pent--yne,,-trimethylnon--yne
13 ' ' ' -(prop--enyl)cyclonon--yne d. e. ' ' ' ' ' '. Problems carboxylic acids ' ' ' ints ' Either the alkene or the alkyne could get # based on the lowest possible number at the first point of difference. Since they are similar here, the alkene gets the # because it is higher priority when all else is equal. -c(yclohex--enyl)hept--en--yne Since the alkyne would get a lower number than the alkene it gets number in this example. -(,-dimethylcyclobut--enyl)non-e-en--yne carboxylic acids prefix = not used in our course (carboxy-) suffix = -oic acid -hydroxy--methoxyheptanoic acid d. d.. carboxylic acid. alcohol. ether Do not count the nitrile carbon in the longest chain when it is a substituent. -amino--cyanopent-e-enoic acid. carboxylic acid. amine. nitrile. alkene -oxohex--ynoic acid. carboxylic acid. ketone. alkyne
14 d. benzoic acid. carboxylic acid. aromatic ring. Problems anhydrides ints carboxylic anhydrides (we just say "anhydride") prefix = not used in our course suffix = -oic anhydride Since both carbon chains are identical you only have to write the name once. butanoic anhydride -methylbutanoic but--enoic anhydride benzoic ethanoic anhydride. Problems esters S ints S ' ' carboxylic esters (we just say "ester") prefix = not used in our course (alkoxycarbonyl-) prefix = alkyl (as branch) suffix = -oate S ' ' no hyphen, separate name ethyl -hydroxy--mercaptobutanoate ' ' '. ester. alcohol. thiol There are two carbon chains to name. The alkoxy side is named in front, as a separate name as though it were a typical branch (-yl ending). It may have its own numbers, but no number is associated with it the way a branch off of the parent chain would have.
15 benzoate phenyl. Problems acid chlorides ' ' ' no hyphen, separate name phenyl benzoate no hyphen, separate name prop--enyl -cyano--ethoxy--oxohex--ynoate "allyl" can be used too Don't confuse phenyl and benzyl. X X. ester. nitrile. ether. alkyne. aldehyde. alkene phenyl-x benzyl-x benzyl phenyl l l Br ints ' ' ' l l Br acid chlorides prefix = chlorocarbonyl- suffix = -oyl chloride l -bromo-,-dioxohex-z-enoyl chloride Br l l. acid chloride. bromo. alkene. ketone. aldehyde ' ' ' l -nitro--propoxy--oxohept--ynoyl chloride. acid chloride. nitro. ether. alkyne. ketone l benzoyl chloride. Problems amides ints. Problems aldehydes ints
16 0. Problems ketones ints. Problems alcohols ints. Problems thiols ints. Problems amines ints. Problems ethers ints. Problems sulfides ints. Problems miscellaneous low priority groups ints. Problems acids ints
17 Some typical alkane examples What are the common names? I Br l F structure A structure B Which carbons are primary, secondary, tertiary or quaternary in structure A, structure B? primary carbon = o = secondary carbon = o = tertiary carbon = o = quaternary carbon = o = 0 ' ' 0 0 ' 0 0 -propyldecane -methyl--propyldecane,-dimethyl--propyldecane,,-trimethyl--propyldecane,-dimethyl--(,-dimethylpropyl)decane -phenyl -isopropyl -butyl -isobutyl -sec-butyl -propyl -t-butyl or -tert-butyl I Br l F structure A structure B primary carbon = o =,,,, secondary carbon = o =, tertiary carbon = o = quaternary carbon = o = Same answers for either structure A or B.
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