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Generic Pattern Specific Example Using Suffix Specific Example Using Prefix O O C H C H R O not used in our course H3C O (it's the highest priority suffix: -oic acid IUPAC: ethanoic acid group that we use) prefix: #-carboxy common:

O O O O O O O

R O R anhydride O O 3 1 OH suffix: -oic -oic anhydride 4 2 (just one -oic anhydride, if symmetrical) IUPAC: ethanooic propanoic anhydride 4-acyloxymethanebutanoic acid prefix: #-acyloxyalkanecarbonyl O O O O R' R O O O 3 1 OH 4 2 suffix: alkyl -oate IUPAC: propyl ethanoate prefix: #-alkoxycarbonyl common: propyl acetate 4-methoxycarbonylbutanoic acid O O O O

R Cl Cl acid chloride Cl 3 1 OH 4 2 suffix: -oyl chloride IUPAC: ethanoyl chloride common: acetylchloride prefix: #-chlorocarbonyl 4-chlorocarbonylbutanoic acid O O alkyl O O R1 R N N o o o (1 ,2 ,3 ) H2N 3 1 OH R2 alkyl 4 2 suffix: N-alkyl-N-alkyl - IUPAC: N-ethyl-N-methylethanamide 4-amidobutanoic acid prefix: #-amido or #-carbamoyl 4-carbamoylbutanoic acid common: N-ethyl-N-methylacetamide N N N C C C O R H C 3 3 1 4 2 suffix: nitrile IUPAC: ethanenitrile OH prefix: #-cyano common: acetonitrile 3-cyanobutanoic acid O O O H O O

R H H H 5 3 1 OH suffix: -al 4 2 prefix: #-oxo (if part of longest chain) IUPAC: ethanal #-formyl (if branch off of longest chain) 3-formyl-5-oxopentanoic acid common: O O O O

R1 R2 3 1 OH 4 2 suffix: -#-one IUPAC: pentan-2-one prefix: #-oxo (older = #-keto) 3-oxobutanoic acid former: 2-pentanone

z:\files\classes\314\314 Functional Groups.doc OH OH O O R H 3 1 OH suffix: -#-ol IUPAC: propan-2-ol 4 2 prefix: #-hydroxy former: isopropyl alcohol 3-hydroxybutanoic acid

O O O O R1 R2 3 1 suffix: none 4 2 prefix: #-alkoxy (< 5C) IUPAC: 1-ethoxypropane OH #-alkyloxy (> 5C) former: ethyl propyl ether 3-methoxybutanoic acid

S SH SH O R H 3 1 4 2 suffix: -#-thiol OH prefix: #-mercapto IUPAC: propan-2-thiol 3-mercaptobutanoic acid #-sulfanyl common: isopropyl mercaptan 3-sulfanylbutanoic acid

S S S O R1 R2 3 1 4 2 suffix: none IUPAC: 1-ethylthiopropane OH prefix: #-alkylthio former: ethyl propyl sulfide 3-methylthiobutanoic acid

R3

N NH O R R N 1 2 3 1 (1o,2o,3o) 4 2 OH suffix: N-alkyl-N-alkyl -#- IUPAC: N-ethyl-N-methylpropanamine prefix: #-(N-alkyl-N-alkylamino) former: ethylmethylpropylamine 3-(N-methylamino)butanoic acid

X Br F O

3 1 OH suffix: none IUPAC: 2-bromopropane 4 2 prefix: #-halo common: isopropyl bromide 3-fluorobutanoic acid

X N3 NO2 O X = -NO = X = NO2 = nitro (X prefix) X = N = azido 3 3 1 OH suffix: none X = N2 = diazo IUPAC: 2-azidopropane 4 2 common: isopropyl prefix: #-see list 3-nitrobutanoic acid O O 4 R E = high priority opposite side 3 1 OH 3 1 OH suffix: none Z = high priority same side IUPAC: 2-methylpropene 2 4 2 common: isobutylene but-2Z-enoic acid but-2E-enoic acid prefix: #-ene O O 1 R 4 2 OH alkene E = high priority opposite side 3 1 OH 3 suffix: none Z = high priority same side IUPAC: ethyne 2 4 common: but-3-ynoic acid but-2-ynoic acid prefix: #-ene n = 0 = n = 6 = octane CH = n = 1 = propane n = 7 = nonane n = 3 = n = 8 = 4 n = 2 = n = 4 = n = 9 = cycononane n = 8 = decane (CH ) n = 3 = 2 n n = 5 = n = 10 = H C n = 9 = 3 (CH2)n CH3 n = 4 = hexane n = 10 = dodecane n = 6 = n = 11 = cycloundecane n = 5 = heptane n = 11 = tridecane n = 7 = n = 12 = z:\files\classes\314\314 Functional Groups.doc

n-, n = normal (Straight chain name based on the total number of atoms present.)

X X X X

n-propyl n-butyl n-pentyl n-hexyl Isoalkanes, iso = 3 with branch off middle carbon. The stem name is based on the total number of carbon atoms present.

X X X X isopropyl isobutyl isopentyl isohexyl This is a unique term applied to only secondary substition on a straight 4C chain.

sec-butyl

X t-alkanes, t = tert = tertiary carbon, having the first pattern and at least 2 methyl groups and a side branch (1C or longer). The stem name is based on the total number of carbon atoms present.

X X X X

t-butyl t-pentyl t-hexyl t-heptyl Neoalkanes have the 5 carbon pattern shown in the first structure (4o carbon in the middle, with 3 methyl groups and a side branch) using the appropriate stem name based on the total number of carbon atoms present.

X X X neopentyl neohexyl neoheptyl Other patterns with special names based on the number of attached carbon atoms (a. to carbon, b. to ). a. H H R R

R C X R C X R C X R C R

H R R R 1 carbon atom 2 carbon atoms 3 carbon atoms 4 carbon atoms attached = primary (1o) attached = secondary (2o) attached = tertiary (3o) attached = quaternary (4o)

b. H H R R

R N R N R N R N R

H R R R 1 carbon atom 2 carbon atoms 3 carbon atoms 4 carbon atoms attached = attached = primary amine attached = secondary amine attached = tertiary amine quaternary ammonium ion Other patterns with special names based on the number of attached atoms. H H R H2 H3C R R C R R C R R C X R C R H2 H3C X R C X R R R 3 hydrogen atoms 2 hydrogen atoms 1 hydrogen atom 0 hydrogen atoms attached = methyl attached = attached = methine attached = no name Special groups having pi bonds. X X X X X

allyl X vinyl X propargyl X benzyl X phenyl X

z:\files\classes\314\314 Functional Groups.doc 1 234 O O O O O

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

5 678 O O O N C R' C R' C H C R N R N R N R

H H R"

9 10 11 O O 12 S O C C R H R H R H R R

13 14 15 16 H R' O S R R H3C CH3 N N R H R H

17 18X 19 R 20 R R' R R N R C C C R C R" R R

21 22 23 24 R O C N N H N R N R O R R O N2 R

z:\files\classes\314\314 Functional Groups.doc 1 234 O O O O O C H C C C C R' R O R O R R Cl R O carboxylic acid anhydride acid chloride ester prefix: #-carboxy- prefix: #-acyloxyalkylcarbonyl- prefix: #-chlorocarbonyl- prefix: #-alkylcarbonyl- suffix: -oic acid suffix: -oic anhydride suffix: -oyl chloride suffix: -oate

5 678 O O O N C R' C R' C H C R N R N R N R

H H R" o o nitrile 1o amide 2 amide 3 amide prefix: #-amido- prefix: see notes prefix: see notes prefix: #-cyano- suffix: -amide suffix: -amide suffix: -amide suffix: -nitrile

9 10 11 O O 12 S O C C R H R H R H R R aldehyde ketone alcohol thiol prefix: #-oxo- prefix: #-oxo- prefix: #-hydroxy- prefix: #-mercapto- suffix: -al suffix: -#-one suffix: -#-ol suffix: -#-thiol

13 14 15 16 H R' O S R R H3C CH3 N N R H R H ether sulfide / thioether 1o amine 2o amine prefix: #-alkoxy- prefix: #-amino- prefix: #-amino- suffix: none prefix: #-alkylthio- suffix: none suffix: -#-amine suffix: -#-amine

17 18X 19 R 20 R R' R R N X = R C C F #-fluoro C R C R" Cl #-chloro R 3o amine Br #-bromo R alkene I #-iodo prefix: #-amino- prefix: none prefix: none suffix: -#-amine prefix: #-halo suffix: none suffix: -#-ene suffix: -#-yne

21 22 23 24 R O C N N H N R N R O R R O N2 alkane R nitroalkane nitrosoalkane diazoalkane prefix: #-alkyl- prefix: #-nitro- prefix: #-nitroso- suffix: -ane prefix: #-diazo- suffix: none suffix: none suffix: none

z:\files\classes\314\314 Functional Groups.doc Several of the groups below have been paired together because they share some common feature. The only difference is that one has a C=O and one does not. These are easy to confuse, so learn them well. Priority #s are listed with FGs.

O O #1 #9 #3 #12 #2 O O H2 C H C H C CH3 H3C CH3 C C H3C O H3C O H C O 3 O H3C O CH3 carboxylic acids anhydrides

#6 #7 O #8 O #4O #12 H2 H CCN C 3 C C C H3C Cl H3C H H3C Cl H3C CH3 acid chlorides chloroalkanes

O O O H CH3 #5 #11 H2 C H C CH N C H 3 C CH3 H3C N N H C N H C CH H3C N 3 H3C N 3 3 H3C CH3 o H 1 amines 2o amines o o o H o 3 amines 1 amides H 2 amides 3 amides CH3

#9 H 2 #10 #12 O #12 C H H3C S S C H H3C CH3 H3C CH3 H3C O H2 ethers alcohols / thioethers

suffix: -ene > -yne > -ane #12 H2 C H H3C CH3 C H CCC H 3 C H3C Br CH3 H2C H2 alkanes bromoalkanes

#12 O #12 #12 #12 H3C N C H2C N N H3C N N N H3C N O H2 C O H2 nitrosoalkanes diazoalkanes azidoalkanes nitroalkanes

z:\files\classes\314\314 Functional Groups.doc Name ______

E CH3N(CH3)2 A B O C CH CO CH H3C CH3 CH N CH3CH2CH3 O 3 2 3 D CH2CHCH3 F 3 3 N N CH3COCH3 H3C CH3 H2C CH C C CH 3 H3C N C 3 C H C CH CH3 N H2 3 3 H3C O H G H I J K L O O CH3CH2Br CH CH NO CH CH SH CH3NHCH3 3 2 3 2 CH3NO2 CH3COCl H3C CH3 H3C Br H C O H3C SH N C 3 N C C H C Cl N H3C O H 3 H2 H2 MNCH CH NH O P Q R O 3 2 2 CH3CH2OH CH3OCH3 CH2N2 CH3CN CH3CONH2 H3C NH2 H C OH H3C CH3 3 C H CCN C C 3 H2C N N O H3C NH2 H2 H2 S T V CH SCH U O O W O O CH3CCH 3 3 CH CHO CH3CO2H CH3CO2COCH3 S 3 C C C C H3CCC H H3C CH3 H C O CH H3C H H3C OH 3 3

1. carboxylic acid 5. amide 9. alcohol 13. 3o amine 17. alkene 20. nitroalkane

2. anhydride 6. nitrile 10. thiol 14. ether 18. alkyne 21. nitrosoalkane

3. ester 7. aldehyde 11. 1o amine 15. sulfide 19. alkane 22. diazoalkane

12. 2o amine 23. azidoalkane 4. acid chloride 8. ketone 16. bromoalkane

Name ______E CH3N(CH3)2

B O C CH CO CH H3C CH3 CH N A CH3CH2CH3 O 3 2 3 D CH2CHCH3 F 3 3 N N CH3COCH3 H3C CH3 H2C CH C C CH 3 H3C N C 3 C H C CH CH3 N H2 3 3 H3C O H G H I J K L O O CH3CH2Br CH CH NO CH CH SH CH3NHCH3 3 2 3 2 CH3NO2 CH3COCl H3C CH3 H3C Br H C O H3C SH N C 3 N C C H C Cl N H3C O H 3 H2 H2 MNCH CH NH O P Q R O 3 2 2 CH3CH2OH CH3OCH3 CH2N2 CH3CN CH3CONH2 H3C NH2 H C OH H3C CH3 3 C H CCN C C 3 H2C N N O H3C NH2 H2 H2 S T V CH SCH U O O W O O CH3CCH 3 3 CH CHO CH3CO2H CH3CO2COCH3 S 3 C C C C H3CCC H H3C CH3 H C O CH H3C H H3C OH 3 3

V D G 1. carboxylic acid 5. amide R 9. alcohol O 13. 3o amine E 17. alkene 20. nitroalkane

K 2. anhydride W 6. nitrile P 10. thiol L 14. ether M 18. alkyne S 21. nitrosoalkane

o N Q 3. ester C 7. aldehyde U 11. 1 amine 15. sulfide T 19. alkane A 22. diazoalkane

F I B 12. 2o amine H J 23. azidoalkane 4. acid chloride 8. ketone 16. bromoalkane z:\files\classes\314\314 Functional Groups.doc A = carboxylic acid B = anhydride C = acid chloride D = ester

O O O O O

C C C C C CH3 H3C OH H3C O CH3 H C O H3C Cl 3

o o o E = amide (1 ,2 ,3 ) O F = nitrile G = aldehyde O O H = ketone O C H O C H C H H3C N H3C N H3CCN C H3C N C H3C H H H3C CH3 H H I = alcohol J = thiol K = ether L = sulfide / thioether

S H3C SH O H3C OH C H C CH H3C CH3 C 3 3 H2 H2

M = amine (1o,2o,3o) N = bromoalkane O = alkene H C CH 3 3 H N 2 H H3C NH2 H3C CH3 C C C N H3C Br H C CH3 H2 H 2 CH3

R = nitroalkane P = alkyne Q = alkane S = nitrosoalkane T = diazoalkane O

H3CCC H H C N H3C CH3 3 H3C N H2C N N C C O H C O H2 2 H 2

A = carboxylic acid B = anhydride C = acid chloride D = ester E = amide

CH3CO2CH3 CH3CONH2 CH3CO2H CH3CO2COCH3 CH3COCl

F = nitrile G = aldehyde H = ketone I = alcohol J = ether K = thiol

CH3CN CH CHO 3 CH3COCH3 CH3CH2OH CH3OCH3 CH3CH2SH

o o o L = sulfide / thioether M = amine (1 ,2 ,3 ) N = bromoalkane O = alkene

CH3SCH3 CH3CH2NH2 CH NHCH CH3N(CH3)2 CH CHCH 3 3 CH3CH2Br 2 3 1o 2o 3o

P = alkyne Q = alkane R = nitroalkane S = nitrosoalkane T = diazoalkane

CH3CCH CH2CHCH3 CH CH NO CH CH NO 3 2 2 3 2 CH2NN

z:\files\classes\314\314 Functional Groups.doc