Lecture2: 123.101
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Lecture2: 123.101 Lecture2: 123.101 Presentation Transcript

  • Unit One Part 2:naming & functional groups H3C O CH3 N H N O N N H3C S O N O N H3C viagra™ (trade name) sildenafil (trivial name) 5-(2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)phenyl)-1- methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one
  • Unit One Part 2:naming & functional groups H3C O CH3 N H N O N N H3C S O N O N H3C viagra™ (trade name) sildenafil (trivial name) panic! Don’t 5-(2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)phenyl)-1- We won’t do anything methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one this complicated
  • Unit One 2Part molecules (pg 11-16)NamingIntroducing functionalgroups (pg 16-9) remember...read the study guide it contains all you need
  • how do wename molecules?
  • O OH NH22-amino-4-methylpentanoic acid prefix parent suffix substituents carbon chain principalminor functional (& multiple functional groups bonds) groups
  • O OH NH22-amino-4-methylpentanoic acid there are three parts to any name...even Viagra’s real name prefix parent suffix obeys this. substituents carbon chain principalminor functional (& multiple functional groups bonds) groups
  • O OH NH22-amino-4-methylpentanoic acid the prefix can become a nightmare as it contains most information prefix parent suffix substituents carbon chain principalminor functional (& multiple functional groups bonds) groups
  • five steps tosuccess!
  • five steps tosuccess! works for all molecules but the whole system takes volumes to explain...
  • 1parentlongest carbonchain containing afunctional group page 12/13 of guide CH3 CH3 OHH3C CH3 H3C 4 2 5 3 1 4-methylheptane 2-propyl-1-pentanol
  • 1parentlongest carbonchain containing afunctional group CH3 7 bigger than 5 he CH3 says patronisingly OHH3C CH3 H3C 4 2 5 3 1 4-methylheptane 2-propyl-1-pentanol
  • 1 parent longest carbon chain containing a functional group CH3 CH3 now use pent- as OHH3C we have to start 3 CH H3C 4 2 5 3 1 our chain from the 4-methylheptane functional group 2-propyl-1-pentanol
  • 2 suffix major functional group list of major groups pg 13 order of priority pg 14 O CH3 OH3C OH H3C NH2 butanoic acid 3-methylbutanamide
  • 2 suffix major functional group O CH3 OH3C OH H3C NH2 butanoic acid 3-methylbutanamide only one major group per molecule
  • 2 minor FG not all groups are equal: halo- & nitro- a (-NO2) are prefixes H3C O Br N CH3 O1-bromo-2-methylpropane nitroethane no idea why! But please remember they are functional groups. It is only for naming that they do not count
  • 3 position of functional group from number longest end of chain chain (parent) from start to finish... O HOH3C CH3 O 2-pentanone 5-methylheptanoic acid pentan-2-oneNOT 4-pentanone
  • 3 position of functional group from end of chain O HO ...giving majorH3C CH3 functional group lowest possible O value 2-pentanone 5-methylheptanoic acid pentan-2-oneNOT 4-pentanone
  • 3 position of functional group from end of chain it doesn’t matter O where number HO goes but I think the second exampleH3C CH3 avoids confusion O later 2-pentanone 5-methylheptanoic acid pentan-2-oneNOT 4-pentanone
  • 4 prefix substituents (and minor functional groups) CH3 Cl CH3 H3C CH3 H3C CH3 H3C CH3 CH3 2,2,5-trimethylheptane 8-chloro-2,3-dimethylnonaneNOT 3,6,6-trimethylheptane NOT 2-chloro-7,8-dimethylnonane
  • 4 prefix substituents (and minor functional groups) CH3 Cl CH3 numbering should H3C CH3 start with major H3C CH functional group3 H3C CH3 (like previous slide) CH3 2,2,5-trimethylheptane 8-chloro-2,3-dimethylnonaneNOT 3,6,6-trimethylheptane NOT 2-chloro-7,8-dimethylnonane
  • 4 prefix substituents (and minor functional groups) CH3 Cl CH3 H3C CH3 H3C CH3 H3C CH3 CH3 2,2,5-trimethylheptane 8-chloro-2,3-dimethylnonaneNOT 3,6,6-trimethylheptane NOT 2-chloro-7,8-dimethylnonane if no major functional group then have lowest numbering for the majority of substituents
  • 4 prefix substituents (and minor functional groups) CH3 Cl CH3 H3C CH3 note: group identical H3C substituentsCH3 (or functional groups) H3C CH3 CH3 together 2,2,5-trimethylheptane 8-chloro-2,3-dimethylnonaneNOT 3,6,6-trimethylheptane NOT 2-chloro-7,8-dimethylnonane
  • 4 prefix substituents (and minor functional groups) CH3 Cl CH3 H3C CH3 H3C CH3 H3C CH3 CH3 2,2,5-trimethylheptane 8-chloro-2,3-dimethylnonaneNOT 3,6,6-trimethylheptane NOT 2-chloro-7,8-dimethylnonane so trimethyl not 2- methyl-2-methyl-6- methylheptane
  • 4 prefix substituents (and minor functional groups) CH3 Cl CH3bizarrely, 3C H halides don’t CH3 count as functional H3C CH3 groups...don’t ask... H3C CH3 CH3 2,2,5-trimethylheptane 8-chloro-2,3-dimethylnonane NOT 3,6,6-trimethylheptane NOT 2-chloro-7,8-dimethylnonane
  • 4 Prefix contains everything except major functional group and multiple bonds O O CH3 H3C OH HO OH H3C CH3 O 5-hydroxy-2,2-dimethyl 2-methyl-4-oxo pentanoic acid hex-2-enoic acidmultiple bonds combined with parent
  • 4 Prefix contains everything except major functional group and multiple bonds functional groups listed on pg 13 O O CH3 H3C OH HO OH H3C CH3 O 5-hydroxy-2,2-dimethyl 2-methyl-4-oxo pentanoic acid hex-2-enoic acidmultiple bonds combined with parent
  • 4 Prefix contains everything except major functional group and multiple bonds O O CH3 major functional group is suffix and is H3C OH HO OH the start of numbering H3C CH3 O 5-hydroxy-2,2-dimethyl 2-methyl-4-oxo pentanoic acid hex-2-enoic acidmultiple bonds combined with parent
  • 4 Prefix contains everything except major functional group and multiple bonds O O CH3 H3C OH all other groups HO OH are prefix H3C CH3 O 5-hydroxy-2,2-dimethyl 2-methyl-4-oxo pentanoic acid hex-2-enoic acidmultiple bonds combined with parent
  • 4 Prefix contains everything except major functional group and multiple bonds alkenes and alkynes are normally part of the parent O O CH3 H3C OH HO OH H3C CH3 O 5-hydroxy-2,2-dimethyl 2-methyl-4-oxo pentanoic acid hex-2-enoic acidmultiple bonds combined with parent
  • 5 order a, b, c...hope you know prefixes are ordered alphabetically your alphabet! (although descriptors like tert are ignored) NH HO OH O 3-hydroxy-2-(methylamino)pentanoic acid NOT 2-(methylamino)-3-hydroxypentanoic acid
  • name this molecule...
  • OH O H3C N CH3 H hept1parent
  • OH O H3C N CH3 H select longest carbon chain (with major functional1 group in it)parent
  • OH O H3C N CH3 H amide2suffix hept identify major functional group – this will be the suffix
  • 6 OH O H3C 5 3 1 N CH3 4 2 H number chain starting with major3 functional group hept amideposition
  • 6 OH O H3C 5 3 1 N CH3 4 2 H 5-methyl4prefix hept amide add prefixes (and remember to tell us where they are by giving a position number)
  • 6 OH O H3C 5 3 N1 CH3 4 2 H 3-hydroxy 6-en repeat with all remaining4 functional groups hept amide 5-methylfunctional groups
  • and the last bit (which throws a nasty curve ball in but don’t worry...) 6 OH O H3C 5 3 1 N CH3 4 2 H N-ethyl4the rest hept amide 5-methyl 3-hydroxy 6-en
  • OH O H3C N CH3 HN-ethyl-3-hydroxy-5-methylhept-6-enamide5order
  • OH O H3C N CH3 HN-ethyl-3-hydroxy-5-methylhept-6-enamide to be honest order5 not too important as long as name is not ambiguousorder
  • N-ethyl? (methylamino)?
  • what the©Renaissance Pictures @&!!#?
  • DON’T PANIC !only simple examples in test
  • On the next slide thereis a skeletal structure and four possible names. 2 Which is correct? example
  • NH2 OHC OH OH OH OA 4-amino-3,5-dihydroxy-5-oxopentanoic acidB 4-amino-3,5,6-trihydroxyhexanoic acidC 3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acidD 4-amino-3,5-dihydroxy-6-oxohexanoic acid
  • NH2 OHC OH OH OH OA 4-amino-3,5-dihydroxy-5-oxopentanoic acid rongB 4-amino-3,5,6-trihydroxyhexanoic acidCD w 3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acid 4-amino-3,5-dihydroxy-6-oxohexanoic acid
  • NH2 OHC OH OH OH OA 4-amino-3,5-dihydroxy-5-oxopentanoic acid The parent contains 6 C. rongB 4-amino-3,5,6-trihydroxyhexanoic acid The carbon C of CHO still w counts!C 3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acidD 4-amino-3,5-dihydroxy-6-oxohexanoic acid
  • NH2 OHC OH OH OH OA 4-amino-3,5-dihydroxy-5-oxopentanoic acidB 4-amino-3,5,6-trihydroxyhexanoic acidCD wrong 3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acid 4-amino-3,5-dihydroxy-6-oxohexanoic acid
  • NH2 OHC OH There are only two alcohol/hydroxy groups. This OH is partof the acid (all bonds to one C). OH OH O A 4-amino-3,5-dihydroxy-5-oxopentanoic acid B 4-amino-3,5,6-trihydroxyhexanoic acid C D wrong 3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acid 4-amino-3,5-dihydroxy-6-oxohexanoic acid
  • NH2 OHC OH OH OH This is not an alcohol OH because of the position of the O C. The C needs four bonds so must have C=OA 4-amino-3,5-dihydroxy-5-oxopentanoic acidB 4-amino-3,5,6-trihydroxyhexanoic acidCD wrong 3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acid 4-amino-3,5-dihydroxy-6-oxohexanoic acid
  • NH2 OHC OH OH OH This is not an alcohol OH because of the position of the O An alcohol C. The C needs four bonds so would be must have C=O HOH2C-A 4-amino-3,5-dihydroxy-5-oxopentanoic acidB 4-amino-3,5,6-trihydroxyhexanoic acidCD wrong 3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acid 4-amino-3,5-dihydroxy-6-oxohexanoic acid
  • NH2 OHC OH OH OH OAB wrong 4-amino-3,5-dihydroxy-5-oxopentanoic acid 4-amino-3,5,6-trihydroxyhexanoic acidC 3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acidD 4-amino-3,5-dihydroxy-6-oxohexanoic acid
  • NH2 OHC OH OH OH OAB wrong 4-amino-3,5-dihydroxy-5-oxopentanoic acid Major functional group 4-amino-3,5,6-trihydroxyhexanoic acid controls the numbering, so the acid is 1.C 3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acidD 4-amino-3,5-dihydroxy-6-oxohexanoic acid
  • NH2 OHC OH OH OH OA 4-amino-3,5-dihydroxy-5-oxopentanoic acidB 4-amino-3,5,6-trihydroxyhexanoic acidC 3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acidD 4-amino-3,5-dihydroxy-6-oxohexanoic acid
  • example3
  • O OH NH2A 2-amino-3-phenylpropanoic acidB 2-amino-1-phenylpropanoic acidC 2-amino-1-hydroxy-3-phenylpropanoneD 2-amino-nona-4,6,8-trienoic acid
  • O OH NH2A 2-amino-3-phenylpropanoic acidB 2-amino-1-phenylpropanoic acidC 2-amino-1-hydroxy-3-phenylpropanoneD 2-amino-nona-4,6,8-trienoic acid
  • O OH NH2A 2-amino-3-phenylpropanoic acidB 2-amino-1-phenylpropanoic acid ...or phenylalanine for those of you of a more biological disposition...C 2-amino-1-hydroxy-3-phenylpropanoneD 2-amino-nona-4,6,8-trienoic acid
  • O OH NH2A 2-amino-3-phenylpropanoic acidB 2-amino-1-phenylpropanoic acidCD wrong 2-amino-1-hydroxy-3-phenylpropanone 2-amino-nona-4,6,8-trienoic acid
  • O OH NH2A 2-amino-3-phenylpropanoic acidB 2-amino-1-phenylpropanoic acidC wrong 2-amino-1-hydroxy-3-phenylpropanone Major functional group controls the numbering, so the acid is 1 and notD 2-amino-nona-4,6,8-trienoic acid the phenyl group
  • O OH NH2AB wrong 2-amino-3-phenylpropanoic acid 2-amino-1-phenylpropanoic acidC 2-amino-1-hydroxy-3-phenylpropanoneD 2-amino-nona-4,6,8-trienoic acid
  • O OH NH2 Both the carbonyl group and the hydroxyl are attached to the same carbon so they are the same rong functional group (a carboxylic acid) wA 2-amino-3-phenylpropanoic acidB 2-amino-1-phenylpropanoic acidC 2-amino-1-hydroxy-3-phenylpropanoneD 2-amino-nona-4,6,8-trienoic acid
  • O OH NH2A 2-amino-3-phenylpropanoic acidBC wrong 2-amino-1-phenylpropanoic acid 2-amino-1-hydroxy-3-phenylpropanoneD 2-amino-nona-4,6,8-trienoic acid
  • O OH NH2 The benzene ring can be considered as aA 2-amino-3-phenylpropanoic acid ong functional group with the name phenyl (if it has wr 1 substituent) or benzene (if it has more than 1 substituent). It should not be calledB 2-amino-1-phenylpropanoic acid cyclohexa-1,3,5-triene or any variant.C 2-amino-1-hydroxy-3-phenylpropanoneD 2-amino-nona-4,6,8-trienoic acid
  • example4
  • O NH2 OH O2NA 2-carbamoyl-4-nitrobenzenolB 2-carbamoyl-4-nitrophenolC 1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehydeD 2-hydroxy-5-nitrobenzamide
  • O NH2 OH O2NA 2-carbamoyl-4-nitrobenzenol ongB 2-carbamoyl-4-nitrophenolCD wr 1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehyde 2-hydroxy-5-nitrobenzamide
  • O NH2 OH O2NA 2-carbamoyl-4-nitrobenzenol ongB 2-carbamoyl-4-nitrophenolCD wr 1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehyde Most of this name is wrong. The amide takes priority and is the suffix (benzamide). If the OH took priority it would be a phenol. 2-hydroxy-5-nitrobenzamide
  • O NH2 OH O2NA 2-carbamoyl-4-nitrobenzenolB 2-carbamoyl-4-nitrophenol wrongC 1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehydeD 2-hydroxy-5-nitrobenzamide
  • O NH2 OH O2NA 2-carbamoyl-4-nitrobenzenolB 2-carbamoyl-4-nitrophenol wrongC 1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehyde Amide still takes priority so it is not a phenolD 2-hydroxy-5-nitrobenzamide
  • O NH2 OH O2N wrongA 2-carbamoyl-4-nitrobenzenolB 2-carbamoyl-4-nitrophenolC 1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehydeD 2-hydroxy-5-nitrobenzamide
  • O NH2 OH O2N wrongA 2-carbamoyl-4-nitrobenzenolB 2-carbamoyl-4-nitrophenolC 1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehyde Both the C=O and the C–N are the same carbon so this is one functional group. It is an amide not an aldehyde and an amine.D 2-hydroxy-5-nitrobenzamide
  • O NH2 OH O2NA 2-carbamoyl-4-nitrobenzenolB 2-carbamoyl-4-nitrophenolC 1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehydeD 2-hydroxy-5-nitrobenzamide
  • draw the moleculewith the followingname...
  • 4-ethyl-3-hydroxycyclohexanone
  • 4-ethyl-3-hydroxycyclohexanone1 parent
  • 4-ethyl-3-hydroxycyclohexanone O2 suffix
  • 4-ethyl-3-hydroxycyclohexanone O4 H3C prefix
  • 4-ethyl-3-hydroxycyclohexanone numbering starts from major functional group O 1 2 3 44 H3C prefix
  • 4-ethyl-3-hydroxycyclohexanone O 1 2 3 4 OH4 H3C functional groups
  • example2
  • 2-hydroxy-3,3-dimethylpentanoic acid OH OH CO2H CO2H A B OH OH O OH CO2H C D
  • 2-hydroxy-3,3-dimethylpentanoic acid OH OH CO2H CO2H ✗ A OH ✔B OH O OH CO2H ✗ C ✗ D
  • 2-hydroxy-3,3-dimethylpentanoic acid Hydroxyl group in wrong position. Numbering starts with the major functional group, the OH OH carboxylic acid CO2H CO2H ✗ A OH ✔ B OH O OH CO2H ✗ C ✗D
  • 2-hydroxy-3,3-dimethylpentanoic acid OH OH CO2H CO2H ✗ A OH ✔B OH O OH CO2H ✗ C ✗ D
  • 2-hydroxy-3,3-dimethylpentanoic acid OH OH CO2H CO2H ✗ A OH ✔B OH O OH CO2H ✗ C ✗ D
  • 2-hydroxy-3,3-dimethylpentanoic acid OH OH CO2H CO2H ✗ A OH ✔ B The carbon chain is OH too short (pent = 5) O OH CO2H ✗ C ✗D
  • 2-hydroxy-3,3-dimethylpentanoic acid OH OH CO2H CO2H ✗ A OH ✔B OH O OH CO2H ✗ C ✗ D
  • 2-hydroxy-3,3-dimethylpentanoic acid OH OH CO2H CO2H ✗ ✔ No carboxylic acid present. Instead we have erroneously A have an aldehyde and an alcohol. B OH OH O OH CO2H ✗ C ✗ D
  • example3
  • 3-bromo-5-methylbenzoic acid O O OH HO Br Br A B O OH O OH Br Br C D
  • 3-bromo-5-methylbenzoic acid O O OH HO ✗ A Br Br ✗ B O OH O OH ✗ Br ✔ Br C D
  • 3-bromo-5-methylbenzoic acid O O OH ✗ ✗ This is not a carboxylic acid. Instead it has both an aldehyde and an alcohol. Carboxylic acids HO Br have the C=O and the OH Br on the same carbon A B atom. O OH O OH ✗ Br ✔Br C D
  • 3-bromo-5-methylbenzoic acid O O OH HO ✗ A Br Br ✗ B O OH O OH ✗ Br ✔ Br C D
  • 3-bromo-5-methylbenzoic acid O O OH HO Bromo is part of the prefix so is attached ✗ A Br Br ✗ Bdirectly to the benzene ring O OH O OH ✗ Br ✔ Br C D
  • 3-bromo-5-methylbenzoic acid O O OH HO Bromo is part of the prefix so is attached ✗ A Br Br ✗ If it was attached to the methyl group B then it would be grouped with thedirectly to the benzene ring O OH O OH methyl (e.g. 3-(bromomethyl)benzoic acid) ✗ Br ✔Br C D
  • 3-bromo-5-methylbenzoic acid O O OH HO ✗ A Br Br ✗ B O OH O OH ✗ Br ✔ Br C D
  • 3-bromo-5-methylbenzoic acid O O OH HO ✗ A Br Br ✗ Numbering is wrong. Carboxylic acid takes priority so the numbering within the ring starts from the carbon B attached to the acid. The drawing shows 2-bromo-5- O OH O OH methylbenzoic acid. ✗ Br ✔Br C D
  • 3-bromo-5-methylbenzoic acid O O OH HO ✗ A Br Br ✗ B O OH O OH ✗ Br ✔ Br C D
  • functional groups these are listed on pg 17
  • Read functionalgroups (Pg16-29) ©hebedesign@flickrI will not have time to go through these
  • alkanes H H C H H methane CH4 propane C3H8 CnH2n+2
  • alkanes H H C H H methane CH4 propane open chains (no C3H8 rings) have this general formula CnH2n+2
  • CnH2n+2 C6H2x6+2 H H H H H HH C6H14 HH H H H H H Reference
  • CnH2n+2 C6H12 ≠ CnH2n+2Functional groups
  • CnH2n+2 C6H12 ≠ CnH2n+2 if a molecule does not agree with this formula, it has either a ring or functional group (look at double bond equivalence (dbe) if you are interested).Functional groups
  • alkanes H H C H H methane CH4 alkanes are tetrahedral in shape...we shall see why later propane C3H8 CnH2n+2
  • alkanes H H C H H methane CH4 alkanes are boring...normally fuels or solvents propane C3H8 CnH2n+2
  • structuralisomers pentane 2-methylbutane 2,2-dimethyl C5H12 C5H12 propane bp 36.2˚C bp 28˚C C5H12 bp 9.6˚C
  • structuralisomers same number of atoms – but bonding different pentane 2-methylbutane 2,2-dimethyl C5H12 C5H12 propane bp 36.2˚C bp 28˚C C5H12 bp 9.6˚C
  • structuralisomers can make big pentane 2-methylbutane differences in 2,2-dimethyl C5H12 C5H12 properties...as propane bp 36.2˚C bp 28˚C shall see later we C5H12 bp 9.6˚C
  • alkenes H H H H ethene trigonal planar
  • alkenes more exciting as the double bond is reactive! H H H H ethene trigonal planar
  • alkenes means it is flat with three groups attached to central atom H H H H ethene trigonal planar
  • configurational (stereoisomers) isomers1-butene 2-methylpropene cyclobutane C4H8 C4H8 C4H8 CH3 H3C CH3 H3C trans-2-butene cis-2-butene C4H8 C4H8 no rotation around C=C bond
  • configurational (stereoisomers) isomers these 2 are structural isomers1-butene 2-methylpropene cyclobutane C4H8 C4H8 C4H8 CH3 H3C CH3 H3C trans-2-butene cis-2-butene C4H8 C4H8 no rotation around C=C bond
  • configurational (stereoisomers) isomers these 2 are stereoisomers. Same1-butene and bonds but atoms 2-methylpropene cyclobutane C4different orientation in H8 C4H8 C4H8 space CH3 H3C CH3 H3C trans-2-butene cis-2-butene C4H8 C4H8 no rotation around C=C bond
  • configurational (stereoisomers) isomers1-butene 2-methylpropene cyclobutane occurs becomes C4H8 C4H8 alkene cannot C4H8 rotate CH3 H3C CH3 H3C trans-2-butene cis-2-butene C4H8 C4H8 no rotation around C=C bond
  • configurational (stereoisomers) isomers a whole world of pain1-butene is coming your way 2-methylpropene cyclobutane C4H8when we discuss C4H8 C4H8 stereoisomers! CH3 H3C CH3 H3C trans-2-butene cis-2-butene C4H8 C4H8 no rotation around C=C bond
  • alkenesin nature H3C CH3 CH3 H3C CH3 H3C(1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene α-pinene
  • alkenesin nature H3C CH3 CH3 H3C CH3 H3C(1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene α-pinene yup...it smells of pine...and is a very useful compound in chemistry
  • alkynesH H triple bond makes ethyne alkynes long C2H2 cylinders O O OMe O O O H3C O OH O MeHN HO O CH3 OH neocarzinostatin chromophore A
  • alkynes H H ethyne C2H2 O they are found in Onature...this nasty OMe Obeast cleaves DNA O O H3C O OH O MeHN HO O CH3 OH neocarzinostatin chromophore A
  • cyclic compounds cyclohexane benzene C6H12 C6H6
  • cyclic compounds some cyclic molecules are flat...because they have flat double bonds cyclohexane benzene C6H12 C6H6
  • cyclic compounds some look flat flat...but are not due to tetrahedral alkane structure (see lct 7) cyclohexane benzene C6H12 C6H6
  • cyclic structuresin nature H3C CH3 CH3 H CH3 H H H3C(8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-(6- methylheptan-2-yl)-hexadecahydro-1H- cyclopenta[a]phenanthrene cholestane - steroid
  • alcohols OH ethanol C2H6O
  • alcohols need OH attached to alkane (not alkene, alkyne or benzene) OH ethanol C2H6O
  • alcohols found in many biological systems... OH ethanol C2H6O
  • alcohols ...especially on Saturday nights... OH ethanol C2H6O
  • alcohols inthe real world HO or Sunday HO HO O mornings... OH HO OH HO 6-(hydroxymethyl)-tetrahydro- 1,2-ethandiol 2H-pyran-2,3,4,5-tetraol ethylene glycol glucose antifreeze sugar I guess!
  • three classesof alcohol H3C CH3 CH3 CH3 secondary (2°) CH3 H CH3H3C OH H H H3C primary (1°) HO (R)-3,7-dimethyloct-6-en-1-ol cholesterol citronellol all animals citronella oil CH3 tertiary (3°) H3C OH CH3 (R)-1-isopropyl-4-methylcyclohex-3-enol terpinen-4-ol tea tree oil
  • three classesof alcohol H3C CH3 CH3 CH3 secondary (2°) CH3 H CH3H3C OH H H H3C primary (1°) HO (R)-3,7-dimethyloct-6-en-1-ol cholesterol citronellol all animals citronella oil CH3 depends on the tertiary (3°) number of carbons3C H OH attached to the C–OH unit CH3 (R)-1-isopropyl-4-methylcyclohex-3-enol terpinen-4-ol tea tree oil
  • three classesof alcohol H3C CH3 CH3 CH3 secondary (2°) ...this one has 1 CH3 H carbon attached so is CH primary. the next 3H3C OH has 2 so is H H3C H secondary etc. primary (1°) HO (R)-3,7-dimethyloct-6-en-1-ol cholesterol citronellol all animals citronella oil CH3 tertiary (3°) H3C OH CH3 (R)-1-isopropyl-4-methylcyclohex-3-enol terpinen-4-ol tea tree oil
  • three classesof alcohol H3C CH3 CH3 CH3 secondary (2°) CH3 H CH3H3C OH H H H3C primary (1°) HO (R)-3,7-dimethyloct-6-en-1-ol cholesterol citronellol all animals citronella oil CH3 this controls the tertiary (3°) reactivity of theH3C OH alcohols as you shall see in future CH3 lectures (R)-1-isopropyl-4-methylcyclohex-3-enol terpinen-4-ol tea tree oil
  • important terms & not just true of alcohols but allcommon mistakes functional groups X X X H H Hprimary secondary tertiary group group group
  • phenols CH3 H3C OH HO H H3C N O phenol O carbolic acid (E)-N-(4-hydroxy-3-methoxybenzyl)- 8-methylnon-6-enamide capsaicin chilli peppers
  • phenols looks like an alcohol BUT is not (as it is not CH3 attached to an alkane) H3C OH HO H H3C N O phenol O carbolic acid (E)-N-(4-hydroxy-3-methoxybenzyl)- 8-methylnon-6-enamide capsaicin chilli peppers
  • phenols thus has very different properties...I should CH3 whistle ‘ring of fire’ now... H3C OH HO H H3C N O phenol O carbolic acid (E)-N-(4-hydroxy-3-methoxybenzyl)- 8-methylnon-6-enamide capsaicin chilli peppers
  • important terms &common mistakes OH OH OH R R R alcohol phenol enol(R = C or H) 1 million times you can more acidic than ignore this one an aliphatic alcohol
  • ethers O O O OH3C O CH3 O O ethoxyethane O diethyl ether tetrahydrofuran ether THF 18-crown-6 replace one carbon in an alkyl chain and you have an ether. Often used as solvents
  • 18-crown-6and potassiumcation
  • halides organic molecules containing fluorine, chlorine, bromine or iodine H F Cl H Cl F Cl Cl dichloromethane dichlorodifluoromethane DCM Freon (refrigerant) a CFC Cl Cl Cl Cl O Cl H Cl H dieldrinPic: NASA
  • halides often toxic and some are responsible for the hole in the ozone H F layer Cl H Cl F Cl Cl dichloromethane dichlorodifluoromethane DCM Freon (refrigerant) a CFC Cl Cl Cl Cl O Cl H Cl H dieldrinPic: NASA
  • thiols SH HS SH CH3 O HS H2N H H3C CH3 H3C CH3 CO2H (R)-2-amino-3- propane-2,2-dithiol 4-methyl-4-sulfanylpropanoic acid sulfanylpentan-2-one cysteine these are the sulfur version of alcohols...found in nature (and us)
  • thiols SH HS SH CH3 O HS H2N H H3C CH3 H3C CH3 CO2H (R)-2-amino-3- propane-2,2-dithiol 4-methyl-4-sulfanylpropanoic acid sulfanylpentan-2-one cysteine one of these is the smelliest chemical known...but no one wants to repeat the experiment to find out which!
  • CH3 2x10-5 ppb HSH3C CH32-(4-methylcyclohex-3- enyl)propane-2-thiol taste of grapefruit can smell nice...garlic, truffles etc...And incredibly small amounts are the taste of grapefruit!
  • CH3 2x10-5 ppb HSH3C CH32-(4-methylcyclohex-3- enyl)propane-2-thiol taste of grapefruit value is similar to this 1 drop in a lake...
  • amines CH3H3C N NH2 H2N H2N NH2 CH3triethylamine butane-1,4-diamine pentane-1,5-diaminesmells of fish putrescine cadaverine smells of decay smells of decay ...also smell bad but are vital for life (and the smell of death).
  • amines innature O CH3 O OH H3C OH H2N H NH2 (S)-2-amino-3- (S)-2-amino-3- phenylpropanoic acid methylbutanoic acid phenylalanine valine amino acid amino acid amino acids are an obvious source of amines
  • amines in nature N CH3 O CH3 O O O methyl 3-(benzoyloxy)-8-methyl- 8-aza-bicyclo[3.2.1]octane-2- carboxylate cocaine Scarface (1983): Universal Pictures
  • amines in nature N CH3 O CH3 O O O methyl 3-(benzoyloxy)-8-methyl- 8-aza-bicyclo[3.2.1]octane-2- carboxylate cocaine but there is a problem bigger than drugs... Scarface (1983): Universal Pictures
  • five kinds of amine H H3C N CH H N H H3C NH2 N 3 H H3C CH3 H3C ammonia methylamine dimethylamine trimethylamine 1° amine 2° amine 3° amine H H3C N CH 3 H3C trimethylammonium ion 4° ammonium (salt)
  • five kinds of amine H H3C N CH H N H H3C NH2 N 3 H H3C CH3 H3C ammonia methylamine dimethylamine trimethylamine 1° amine 2° amine 3° amine H but primary, secondary & tertiary H3C N CH mean something 3 different than when H3C we used them with trimethylammonium ion alcohols! 4° ammonium (salt)
  • five kinds of amine H H3C N CH H N H H3C NH2 N 3 H H3C CH3 H3C ammonia methylamine dimethylamine trimethylamine 1° amine 2° amine 3° amine H ...now refer to thenumber of C attached H3C N CH to the N...but it gets 3 worse... H3C trimethylammonium ion 4° ammonium (salt)
  • the problemwith amines primary amine because only 1 primary amine carbon attached (1°) NH2 H3C OH CH3 O secondary position (2°)
  • the problemwith amines but in a secondary primary amine (like alcohol position (1°)naming) as this carbon has 2 carbons attached! NH2 H3C OH CH3 O secondary position (2°)
  • carbonyl:aldehydes O O O H H H H3C H methanal ethanal benzaldehyde formaldehyde acetaldehyde OH OH O HO OH OH H (2R,3S,4R,5R)-2,3,4,5,6- pentahydroxyhexanal glucose
  • carbonyl:aldehydes O O O H H H H3C H methanal ethanal C=Obenzaldehyde is the cornerstone formaldehyde acetaldehyde of organic synthesis. Aldehydes = CHO and are more reactive than... OH OH O HO OH OH H (2R,3S,4R,5R)-2,3,4,5,6- pentahydroxyhexanal glucose
  • carbonyl:ketones CH3 CH3 O O O H3C CH3 H3C H H CH3(R)-2-methyl-5-(prop-1-en- propanone (S)-2-methyl-5-(prop-1-en- 2-yl)cyclohex-2-enone acetone 2-yl)cyclohex-2-enone (R)-carvone (S)-carvone spearmint caraway
  • carbonyl:ketones ketones, which have CH3 C=O bonded to two CH3 carbon groups O O O H3C CH3 H3C H H CH3(R)-2-methyl-5-(prop-1-en- propanone (S)-2-methyl-5-(prop-1-en- 2-yl)cyclohex-2-enone acetone 2-yl)cyclohex-2-enone (R)-carvone (S)-carvone spearmint caraway
  • carboxylic acidderivatives: acids H3C CH3 CH3 O O H3C OHH3C OH CO2H OH O CH3ethanoic acid (S)-2-hydroxy- (2Z,4E)-3-methyl-5-(2,6,6- acetic acid propanoic acid trimethyl-4-oxocyclohex-2- vinegar L-(+)-lactic acid enyl)penta-2,4-dienoic acid abscisic acid C=O bonded to 1 leaf fall carbon and an OH group
  • carboxylic acidderivatives: others O O H3C CH3 Na O H3C O CH3 sodium ethanoate 2-methylpropyl propanoate carboxylate ion isobutyl propionate smell of rum ester NH2 O H HO2C N many different OMe derivatives depending on what O is attached to C=O aspartame sweetener amide
  • important terms &common mistakes OH O O O R R OH OH alcohol aldehyde NOT carboxylicR = C or H an aldehyde acid + an alcoholatoms attached to the same carboncount as one functional group
  • important terms &common mistakes NH2 O O O R R NH2 NH2 amine aldehyde NOT amideR = C or H an aldehyde + an amineatoms attached to the same carboncount as one functional group
  • important terms &common mistakes OHC-R ≠ HOC-R O ≠ H C C O RH R This actually meaningless as Learn to draw the C does not have 4 bonds accurately
  • how are functional groups related?
  • H oxidation H oxidation H oxidation OH R C H R C H R C R C reduction reduction reduction H OH O Ohydrocarbon alcohol aldehyde carboxylic acid carboxylic acids alcohols esters ethers aldehydes amidesalkanes amines ketones acyl halides halides acid anhydrides thiols nitriles
  • Read this unit againLearn the functional groups ©sidewalk flying@flickr
  • what have....we learnt? • naming (simple) HO molecules HO • recognise functional groups OH Me O Me O O NH2 O Cl OH O O HO Cl OH O O O H H O N N NHMe N N N H H H HN O O O Me molecules may look HO2C complicated but simply NH2 Me break them down into their functional groups OH (amides in red) HO OH Vancomycin
  • parts 3 & 4are combined word of warning...next 2 units will not be in the same order as study guide...
  • readPages 35, 37,41-42, 45-47 ©Fiduz@flickr