sign in sign up
<<
Home , Haloalkane

Generic Pattern Specific Example Specific Example in ordero of nomenclature priority Using Suffix (2D and 3D) Using Prefix when in our course. when highest priority FG lower priority FG 1. (2D) carboxylic acid (3D)

O Condensed line formula IUPAC: ethanoic acid O H H prefix example C H common: acetic acid RCO2H or HO2CR C C R O #-carboxy H O RCH(CO H)R' H suffix: -oic acid 2 O not used in our course FG on FG on C H (acids are the highest priority prefix: #-carboxy the right the left H3C O group that we use) FG in the carbonyl resonance (2D) middle (C=O) is possible

2. anhydride (2D) Condensed line formula anhydride (3D) IUPAC: ethanoic propanoic anhydride O O RCO2COR' or ROCO2CR' H H O O H C C C CH C 3 R O R H3C O C H H 2 prefix example H O C H suffix: -oic -oic anhydride (2D) (just one -oic anhydride, O O O C C O if symmetrical) 3 1 H 4 H 2 prefix: #-acyloxyalkanecarbonyl O O OH (prefix not required for us) carbonyl resonance 4-acyloxymethanebutanoic acid (C=O) is possible (prefix not required for us - too difficult)

3. (2D) name (goes in front as separate word) ester (3D) H H H IUPAC: propyl ethanoate O C Condensed line formula C O C common: propyl acetate C R' H H R O RCO2R' or R'O2CR H H C C H O H H2 RCH(CO2CH3)R' prefix: alkyl suffix: -oate H C C CH3 O H C O C prefix example 3 H prefix: #-alkoxycarbonyl 2 O O (2D) 3 1 carbonyl resonance 4 2 (C=O) is possible O OH 4-methoxycarbonylbutanoic acid

4. acid chloride (2D) carboxylic acid (3D) IUPAC: ethanoyl chloride prefix example O Condensed line formula O O Cl common: acetylchloride C RCOCl or ClOCR H 3 1 R Cl 4 2 C C O Cl OH RCH(COCl)R' H suffix: -oyl chloride H O C 4-chlorocarbonylbutanoic acid H C Cl prefix: #-chlorocarbonyl 3 (2D) carbonyl resonance (C=O) is possible, but weak because of the poor overlap of the 3p orbital with the 2p orbital

Y:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, Resonance.doc o o o o 5. (1 ,2 ,3 ) (2D) 3 (3D) IUPAC: N-ethyl-N-methylethanamide H H O Condensed line formula H H common: N-ethyl-N-methylacetamide alkyl C C O C R' H H RCONR2 or R2NOCR H2 R N H N C C C ' H H3C N CH3 R" alkyl RCH(CONH2)R C C H H CH when highest priority functional group H (2D) 3 prefix example 1o amides: suffix: -amide O O O 2o amides: prefix: N-alkyl suffix: -amide 3o amides: prefix: N-alkyl-N-alkyl suffix: -amide carbonyl resonance (C=O) H N 3 1 OH is possible, it is especially 2 4 2 prefix when lower priority functional group: strong in amides o 1 amides: prefix: #-amido or #-carbamoyl 4-amidobutanoic acid 2o amides: prefix: #-(N-alkylamido) or #-(N-alkylcarbamoyl) or 3o amides: prefix: #-(N-allkyl-N-alkylamido) or #-(N-alkyl-N-alkylcarbamoyl) 4-carbamoylbutanoic acid

6. (2D) nitrile (3D) IUPAC: ethanenitrile prefix example N Condensed line formula H N C common: acetonitrile R RCN or NCR C C N C O H suffix: nitrile N 3 1 RCH(CN)R' H (don't drop the final C 4 2 "e" of the stem name) nitrile resonance OH H3C (CºN) is possible (2D) prefix: #-cyano 3-cyanobutanoic acid

7. (2D) aldehyde (3D) IUPAC: ethanal Condensed line formula H O common: acetaldehyde prefix examples RCHO or OHCR C O C O H H O O O R H RCH(CHO)R' C 5 3 1 suffix: -al H C 4 2 H H3C H H OH prefix: #-oxo (if part of longest chain) carbonyl resonance (2D) (C=O) possible 3-formyl-5-oxopentanoic acid #-formyl (if branch off of longest chain)

8. (2D) ketone (3D) Condensed line formula H H O IUPAC: pentan-2-one C prefix example H R1COR2 or R2OCR1 C H H former: 2-pentanone O O R R' H H C O RCH(COCH )R' 3 C 3 1 C O 4 2 suffix: -#-one C C OH H H2 H H prefix: #-oxo (older = #-keto) H H C C H3C C CH3 3-oxobutanoic acid carbonyl resonance H2 (C=O) possible (2D)

9. (2D) Condensed line formula alcohol (3D) IUPAC: propan-1-ol prefix example H H former: 1-propanol OH O O RCH2OH or HOH2CR H H R H C H common: n-propyl alcohol 3 1 RCHOHR' C 4 2 suffix: -#-ol C O OH H H2 H C OH prefix: #-hydroxy H 3-hydroxybutanoic acid H3C C H2 (2D)

Y:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, Resonance.doc 10. (2D) thiol (3D) Condensed line formula IUPAC: propan-1-thiol prefix example S H H SH O R H H H common: propyl mercaptan R CH SH or HSH CR 1 2 2 1 C H 3 1 suffix: -#-thiol C 4 2 (don't drop the final C S H2 OH R1CHSHR2 H C SH "e" of the stem name) H H H C C 3-mercaptobutanoic acid 3 (2D) prefix: #-mercapto H2 3-sulfanylbutanoic acid #-sulfanyl

11. (1o,2o,3o) (2D) Condensed line formula 3o (3D) R' RNH H NR H H H 2 2 H H H IUPAC: N-ethyl-N-methylpropan-1-amine N R(NR')R" C C H R R" C former: ethylmethylpropylamine RCH(NH2)R' C N C H when highest priority functional group H o H H H 1 amines: suffix: -amine H prefix example 2o amines: prefix: N-alkyl suffix: -amine C o H H 3 amines: prefix: N-alkyl-N-alkyl suffix: -amine NH O CH3 3 1 prefix when lower priority functional group: H2 4 2 1o amines: prefix: #-amino C N CH3 OH H C C C 2o amines: prefix: #-(N-alkylamino) 3 H2 H2 (2D) o 3-(N-methylamino)butanoic acid 3 amines: prefix: #-(N-allkyl-N-alkylamino)

12. (2D) Condensed line formula ether (3D) O R OR H H H R1 R2 1 2 H H H C C H C prefix example suffix: none R1CH(OCH3)R2 C O C H IUPAC: 1-ethoxypropane prefix: #-alkoxy (< 5C) H H H H O O common: ethyl propyl ether #-alkyloxy ( 5C) H 3 1 2 4 2 C O CH3 OH H C C C 3 H H (2D) 2 2 3-methoxybutanoic acid

12. (2D) Condensed line formula ether (3D) S RSR' H H H R1 R2 H H H C C H RCH(SCH )R' C prefix example suffix: none 3 C S C IUPAC: 1-ethylthiopropane H H S O prefix: #-alkylthio H H H former: ethyl propyl sulfide 3 1 H 4 2 2 OH C S CH3 H C C C 3 (2D) 3-methylthiobutanoic acid H2 H2

12. haloalkane (2D) bromoalkane (3D) prefix example X = -F = fluoro Condensed line formula Br X H H X = Cl = chloro H H (2D) F O X = Br = bromo CH CH RCH2 Cl or ClH2CR C X = I = iodo C H3C CH3 R R' C H 3 1 OH H 4 2 suffix: none RCHClR' H IUPAC: 2-bromopropane Br prefix: #-halo common: isopropyl 3-fluorobutanoic acid

Y:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, Resonance.doc 12. (2D) Condensed line formula nitroso (3D) prefix example H 2 IUPAC: 1-nitrosopropane H C C R1CH2 NO or ONH2CR H H O 3 N O C NO N O H C H2 2 RCH(NO)R' H C H C C O 3 1 C 3 4 2 suffix: none C N OH H H H2 H H prefix: #-nitroso (2D) 3-nitrosobutanoic acid

nitroso (3D) 12. nitro (2D) Condensed line formula IUPAC: 1-nitropropane O H2 RCH2 NO2 or O2NCH2R H3C C C NO H H 2 N O H2 prefix example H2 RCH(NO2)R' C H3C C O H C C N suffix: none C H 2 O O H H prefix: #-nitro H H O N O (2D) resonance 3 1 4 2 OH resonance O 3-nitrobutanoic acid H2 H H H3C C O N O C N C H2 H C C O H H H H

(3D) 12. (2D) IUPAC: 1-azidopropane Condensed line formula H2 H C C common: propyl azide 3 H C N RCH2 N3 or N3CH2R H H 3 2 N N N H2 N prefix example C RCHN R' H C H3C C N 3 C C N suffix: none H N3 O H H 2 H H prefix: #-azido 3 1 (2D) 4 2 OH resonance resonance 3-azidobutanoic acid

H N H H 2 H3C C N N N N C C N H C H2 C H H H H

12. diazo (2D) diazo (3D) Condensed line formula H IUPAC: 1-diazobutane H3C C RCH N2 or N2CHR C N H H H H 2 2 C N N H2 N RCH(N )R' C 2 H C H3C C N prefix example suffix: none C C C H N O H H 2 2 H H (2D) prefix: #-diazo H 3 1 2 4 OH resonance resonance 3-diazobutanoic acid

H N H 2 H H H3C C N C N N C C C H C H2 C H H H H H

Y:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, Resonance.doc

(always a suffix on the stem name) O O H 4 R R O H 3 1 OH CC H C C 4 2 3 1 OH IUPAC: 2-methylpropene 2 C C R R O common: isobutylene H but-2Z-enoic acid H but-2E-enoic acid suffix: #-ene H E = high priority opposite side

prefix: none Z = high priority same side

(always a suffix on the stem name) H O O C H O H 1 C 4 2 R C C C C 3 OH IUPAC: ethyne 3 1 OH H 2 4 suffix: #-ene but-2-ynoic acid common: acetylene H O prefix: none but-3-ynoic acid E/Z is not possible

alkenes and alkynes (always a suffix on the stem name, -#-en-#-yne) O R H O H C CCR 1 OH H C C C C 2 R C 5 3 C C 6 R O 4 H suffix: #-en-#-yne H H hex-4E-en-2-ynoic acid IUPAC: 2-methylpent-1-en-3-yne prefix: none

aromatics (2D) 3D aromatic IUPAC: methylbenzene branches H R R H common: H H benzyl C C H C C H C C R C C R C C CH H C C C H H CC H CC H phenyl C C R R H H many special names H H (2D) 3D aromatic H H H H H C C H C C H C C C C C C C C C H H CH H C C C C CC H C C H H H H H H H H 1-phenylpent-3E-en-1-yne

n = 0 = () n = 7 = nonane (9C) cycloalkanes n = 1 = propane (3C) n = 8 = decane (10C) n = 3 = cyclopropane n = 9 = cycononane n = 2 = butane (4C) n = 9 = undecane (11C) n = 4 = cyclobutane n = 10 = cyclodecane CH4 = (1C) n = 3 = pentane (5C) n = 10 = dodecane (12C) n = 5 = cyclopentane (CH ) n = 11 = cycloundecane n = 4 = hexane (6C) n = 11 = tridecane (13C) 2 n n = 6 = cyclohexane n = 12 = cyclododecane n = 5 = heptane (7C) n = 12 = tetradecane (14C) n = 7 = cycloheptane H C (CH ) CH n = 13 = cyclotridecane 3 2 n 3 n = 6 = octane (8C) n = 13 = pentadecane (15C) n = 8 = cyclooctane n = 14 = cyclotetradecane

Y:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, Resonance.doc Functional Group Combinations

O NH2 O H OH O O O O O

N O C NH2 Br Cl O O O H

Possible answer (each side is a separate word because this is an anhydride = 2 x “-oic” + anhydride)

1

1 3 2 5Z 3Z 2S 1 3 2 4 1 1 1 O NH2 O H OH O O O O O 12 4 2 2 6 8 10 N 5 3 11O 3 5 7 9 11 13 C 8 6 4 9 7 NH 1 SH Br 10 2 5 Cl O 1 2 2 9 2 3 O O H 8 12S 11 4 3 3 7 4 1 2 1 5 6 4 3 2 4 3 10R 6 5 7 1 4 2S-amino-3-amido-4-phenyl-5-hydroxy-8,11-dioxo-9-methoxycarbonyl-10-cyanoundec-3Z-en-6-ynoic

2-(5-methylcyclopent-2-enyl)-3-benzyl-6-chlorocarbonyl-8-(4-heptylcyclonona-2E,4Z-dienyl)-9-formyl-

10R-mercapto-11-(1-methylpropoxy)-12S-bromotridec-5Z-enoic anhydride

Y:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, Resonance.doc Functional Group Combination

N O H O NH2 O O C O O Cl

O S H3C NH2 Cl SH O O OH O H

Possible answer (each side is a separate word, the first word is the name of the “alkyl” branch attached to the ester oxygen on the left side and the second part is the name of the branch with the on the right side). 1 1

3 2 4 1 5 2R 3Z 5E 2 3 1 4 N 1 1 O H O NH2 O O C O O Cl 1 4 6 2 2 4 6 8 10 12 5 3 O 3 7 9 11 7 1 5 13 2 3 S 10 8 H3C 9 NH2 Cl SH 1 12S 5 1 2 O O 2 OH 9 4 3 1 4 O 11 H 8 3 1 3 2 1 4 7 5 10S 3 2 6 2 3 5 4 4 5 4 1 7 6 8 6

(space) 2R-amino-3-formyl-4-benzyl-5,11-dioxo-8-hydroxy-9-chlorocarbonyl-10-methylthioundec-3Z-en-6-ynyl

2-(4-ethyl-5,5-dimethylcyclopent-2-enyl)3-phenyl-5-cyano-6-methoxycarbonyl-8-(4-hexyl-7-octylcyclonona-2E,5Z-dienyl)- 9-amido-10S-chloro-11-(1-ethylbutoxy)-12S-mercaptotridec-5E-enoate

Y:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, Resonance.doc Common Resonance Patterns

There are 2 types of donors: a. lone pair electrons and b. carbon-carbon pi bonds (alkenes, alkynes and aromatic rings). There are 2 types of acceptors: empty carbon 2p orbitals (carbocations) and pi bonds of all types.

1. Lone pair electron pair donors (acceptors sites are empty carbon 2p orbitals (carbocations) and other pi bonds

N acceptor These anions only exists in X R C acceptor very basic conditions, the > > O acceptor > donor orbital has to be a 2p R R

R N acceptor > O acceptor > F acceptor Neutral lone pairs. R R acceptors = empty carbon 2p orbitals and any kind of pi bond

2. Lone pair donation into pi bonds – lone pairs can be anions or neutral, there are many variations. The pi bond acceptors below can be C=C, CC, C=O, C=N, CN and N=O and more. The more electronegative the pi bond is, the better pi acceptor it is.

anions (2D) neutral (2D) R R R R R R R C R R C R R C R C R C R C N N N C C C O O O N F O R R R R resonance resonance resonance resonance R R R R R R R C R C R C R C R C C N N O O N C R C R C O N F O R R R R

(3D) R R R R resonance R R resonance R R CC CC CC CC X X R R X R X R

2 (2D) sp R R (3D) R C C N C C N R C C N C C N R R

sp R R

Y:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, Resonance.doc 3. Lone pair donation (donor atoms: N > O > F) into an empty carbon 2p orbital (usually a sp2 carbocation and that’s all we’ll show)

cations R H H X R N O F

XC C C C C R R R R R R R R R R H H X N O F R XC C C C C R R R R R R R R R The better resonance structure has more bonds and full octets.

We don't usually show this resonance structure. OK OK R R R X R C N O XC C C C C R R R R R R R R R

R R R X C N O R XC C C C C R R R R R R R R R Usually this resonance is shown in the opposite direction.

4. Only carbon-carbon pi bonds can act as pi donors (alkenes, alkynes and aromatics) into carbon empty 2p orbitals or other acceptor pi bonds of many types (C=C, CC, C=O, C=N, CN, N=O and more.).

Carbon-carbon pi bond donation into an empty carbon 2p orbital (usually an sp2 carbocation)

sp2 carbon R R sp2 carbon sp carbon R R R C R R C R C C C C R CCC R CCC

R R R R R R

R R R R R R CC CC R C CC R C CC R C R R C R R R R R

Y:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, Resonance.doc Aromatic rings can donate or accept electron density from substituent positions (example of each below).

R R R R R R R R C C R C C R C C R C C R R C C C R C C C R C C C R C C C CC R CC R CC R CC R R R R R R R R R R R R R R R R R C C C C R R C C C C R C R C R R C C C C R C R C C C C C R R R R C C C C C C C C R R R R R R R R R R R R R R R R C C C C R C C R C C R R C C O R C C C R C C C R C C C CC CC R CC R CC R R R R R R R R R R R R R R R R R C C C C C C C C R C R C C O C O R C R C C O C O

C C C C C C C C R R R R R R R R

Carbon-carbon pi bond donation into another pi bond (more polar is better, but even C=C is ok.

R R R C O C O C O R R R CC CC CC R R R R R R R R R

R C O R C O R C O C C C C C C R R R R R R

R R R C C N C C N C C N

R C R C R C

R R R R R R N N N C C C C C C R C R C R C R R R

Y:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, Resonance.doc 12O O O 3 O 4 O 5 O a. aromatic b. fluoro C H C C C H C C R' c. carboxylic acid R O R O R' R Cl R O R N d. 1o amine H e. 2o amide RCO2H RCO2COR RCOCl RCO2R' RCONH2 f. nitrile g. thiol 6 O 7 O 8 9 10 h. ether O O N i. bromo C R' C R' C j. acid chloride C C R N R N R R H R R' k. ketone H R" l. sulfide m. RCONHR' RCONR'R" (R  R'  R") RCN RCHO RCOR' n. nitro RCONR'2 (R'  R") o. 3o amide H p. 11 12 13 H 14 15 R" O S q. aldehyde R H R H N N N r. nitroso R R' R H R R' s. alcohol t. iodo ROH RSH RNH2 RNHR' RNR'R" u. 2o amine v. w. chloro 16 17 19 20 18 Br Cl F o O S x. 3 amine R R R R R' R R' y. azido z. anhydride ROR' RSR' RBr RCl RF aa. 1o amide bb. diazo cc. ester 23 24 R 25 dd. alkene/alkyne 21 I 22 R R' O R C C C R R C C C N R C R C R O RI RCCR' R R R2CCR2 R RNO2 RCCCRCR2

26 27 28 29 R 30 H N R O N R R N N N N R2C RH RNO RN3 R2CN2 RC6H5

Y:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, Resonance.doc O 1 O 2 O O 3 O 4 O 5 C C H C C C C R' H R N R O R O R' R Cl R O o carboxylic acid anhydride ester 1 amide acid chloride H *2 *1 prefix: #-acyloxyalkylcarbonyl prefix: #-alkoxycarbonyl prefix: #-carboxy prefix: #-chlorocarbonyl prefix: #-amido or #-carbamoyl suffix: -oic anhydride (R = R') suffix: -oate suffix: -oic acid suffix: -oyl chloride (R' name as branch at front) -oic -oic anhydride (R  R') suffix: -amide O O O 6 7 8 9 10 O N C R' C C R' C R N R N C R H R aldehyde R R' 2o amide 3o amide ketone H R" nitrile prefix: #-oxo- (in chain) prefix: #-oxo prefix: #-(N-alkylamido) prefix: #-(N-alkyl-N-alkylamido) prefix: #-cyano or #-formyl (as branch) #-(N-alkylcarbamoyl) #-(N-alkyl-N-alkylcarbamoyl) suffix: -#-one suffix: -nitrile suffix: #-al suffix: -amide suffix: -amide name R' as N-alkyl in front name R',R" as N-alkyl-N-alkyl in front

11 12 13 H 14 H 15 R" O S R H R H N N N R H R R' R R' alcohol thiol o 1 amine o 3o amine prefix: #-mercapto 2 amine prefix: #-hydroxy or #-sulfanyl prefix: #-amino prefix: #-(N-alkylamino) prefix: #-(N-alkyl-N-alkylamino)- suffix: -#-ol suffix: -#-thiol suffix: -#-amine suffix: -#-amine suffix: -#-amine

16 17 18 19 20 O S Br Cl F R R' R R' R R ether R sulfide bromoalkane chloroalkane fluoroalkane prefix: #-alkoxy (5C) #-alkyloxy (> 5C) prefix: #-alkylthio prefix: #-bromo prefix: #-chloro prefix: #-fluoro

suffix: none suffix: none suffix: none suffix: none suffix: none R 24 R 25 21 I 22 23 R' O *3 R C C C R R N C C C iodoalkane R C R R O alkyne C alkene alkenyne nitroalkane prefix: #-iodo R R R prefix: none prefix: none prefix: none prefix: #-nitro suffix: none suffix: -#-ene suffix: -#-yne suffix: -#-en-#-yne suffix: none 26 30 27 N *3 28 29 R R O N *3 H R N N N R N H C nitrosoalkane 2 azidoalkane diazoalkane alkane prefix: #-nitroso aromatic prefix: #-alkyl prefix: #-azido prefix: #-diazo many special suffix: none suffix: -ane suffix: none suffix: none names *1: not used because we don't use any higher priority group *2: not used because it is too complicated for our level *3: formal charge and resonance

Y:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, Resonance.doc 12O O O 3 O 4 O 5 O

C H C C C C R' C H R O R O R' R Cl R O R N

RCO2H RCO2COR RCOCl RCO2R' RCONH2 H carboxylic acid anhydride acid chloride ester 1o amide

6 O 7 O 8 9 10 O O N C R' C R' C C C R N R N R R H R R' RCONHR' H RCONR'R" R" RCHO RCN RCOR' 2o amide 3o amide nitrile aldehyde ketone

H 11 13 H 14 15 R" O 12 S R H R H N N N R R' R H R R' ROH RSH RNH2 RNHR' RNR'R" alcohol thiol 1o amine 2o amine 3o amine

16 17 19 20 18 Br Cl F O S R R R R R' R R'

ROR' RSR' RBr RCl RF

ether sulfide bromoalkane chloroalkane fluoroalkane

R 21 22 R 23 24 25 O I R' C C R C R R C C C N R C R R O RI C R CCR RCCR' R R 2 2 R RCCCRCR2 RNO2 iodoalkane alkene alkyne alkenyne nitroalkane

26 27 28 29 R 30 H N R O N R R N N N N R2C RH RNO RN3 R CN 2 2 RC6H5 nitrosoalkane azidoalkane diazoalkane aromatic alkane

Y:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, Resonance.doc