Lecture2: 123.101

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Lecture2: 123.101

  1. 1. 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
  2. 2. 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
  3. 3. Unit One 2Part molecules (pg 11-16)NamingIntroducing functionalgroups (pg 16-9) remember...read the study guide it contains all you need
  4. 4. how do wename molecules?
  5. 5. O OH NH22-amino-4-methylpentanoic acid prefix parent suffix substituents carbon chain principalminor functional (& multiple functional groups bonds) groups
  6. 6. 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
  7. 7. 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
  8. 8. five steps tosuccess!
  9. 9. five steps tosuccess! works for all molecules but the whole system takes volumes to explain...
  10. 10. 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
  11. 11. 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
  12. 12. 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
  13. 13. 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
  14. 14. 2 suffix major functional group O CH3 OH3C OH H3C NH2 butanoic acid 3-methylbutanamide only one major group per molecule
  15. 15. 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
  16. 16. 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
  17. 17. 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
  18. 18. 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
  19. 19. 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
  20. 20. 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
  21. 21. 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
  22. 22. 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
  23. 23. 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
  24. 24. 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
  25. 25. 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
  26. 26. 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
  27. 27. 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
  28. 28. 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
  29. 29. 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
  30. 30. 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
  31. 31. name this molecule...
  32. 32. OH O H3C N CH3 H hept1parent
  33. 33. OH O H3C N CH3 H select longest carbon chain (with major functional1 group in it)parent
  34. 34. OH O H3C N CH3 H amide2suffix hept identify major functional group – this will be the suffix
  35. 35. 6 OH O H3C 5 3 1 N CH3 4 2 H number chain starting with major3 functional group hept amideposition
  36. 36. 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)
  37. 37. 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
  38. 38. 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
  39. 39. OH O H3C N CH3 HN-ethyl-3-hydroxy-5-methylhept-6-enamide5order
  40. 40. 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
  41. 41. N-ethyl? (methylamino)?
  42. 42. what the©Renaissance Pictures @&!!#?
  43. 43. DON’T PANIC !only simple examples in test
  44. 44. On the next slide thereis a skeletal structure and four possible names. 2 Which is correct? example
  45. 45. 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
  46. 46. 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
  47. 47. 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
  48. 48. 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
  49. 49. 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
  50. 50. 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
  51. 51. 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
  52. 52. 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
  53. 53. 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
  54. 54. 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
  55. 55. example3
  56. 56. 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
  57. 57. 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
  58. 58. 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
  59. 59. 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
  60. 60. 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
  61. 61. 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
  62. 62. 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
  63. 63. 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
  64. 64. 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
  65. 65. example4
  66. 66. O NH2 OH O2NA 2-carbamoyl-4-nitrobenzenolB 2-carbamoyl-4-nitrophenolC 1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehydeD 2-hydroxy-5-nitrobenzamide
  67. 67. O NH2 OH O2NA 2-carbamoyl-4-nitrobenzenol ongB 2-carbamoyl-4-nitrophenolCD wr 1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehyde 2-hydroxy-5-nitrobenzamide
  68. 68. 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
  69. 69. O NH2 OH O2NA 2-carbamoyl-4-nitrobenzenolB 2-carbamoyl-4-nitrophenol wrongC 1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehydeD 2-hydroxy-5-nitrobenzamide
  70. 70. 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
  71. 71. O NH2 OH O2N wrongA 2-carbamoyl-4-nitrobenzenolB 2-carbamoyl-4-nitrophenolC 1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehydeD 2-hydroxy-5-nitrobenzamide
  72. 72. 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
  73. 73. O NH2 OH O2NA 2-carbamoyl-4-nitrobenzenolB 2-carbamoyl-4-nitrophenolC 1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehydeD 2-hydroxy-5-nitrobenzamide
  74. 74. draw the moleculewith the followingname...
  75. 75. 4-ethyl-3-hydroxycyclohexanone
  76. 76. 4-ethyl-3-hydroxycyclohexanone1 parent
  77. 77. 4-ethyl-3-hydroxycyclohexanone O2 suffix
  78. 78. 4-ethyl-3-hydroxycyclohexanone O4 H3C prefix
  79. 79. 4-ethyl-3-hydroxycyclohexanone numbering starts from major functional group O 1 2 3 44 H3C prefix
  80. 80. 4-ethyl-3-hydroxycyclohexanone O 1 2 3 4 OH4 H3C functional groups
  81. 81. example2
  82. 82. 2-hydroxy-3,3-dimethylpentanoic acid OH OH CO2H CO2H A B OH OH O OH CO2H C D
  83. 83. 2-hydroxy-3,3-dimethylpentanoic acid OH OH CO2H CO2H ✗ A OH ✔B OH O OH CO2H ✗ C ✗ D
  84. 84. 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
  85. 85. 2-hydroxy-3,3-dimethylpentanoic acid OH OH CO2H CO2H ✗ A OH ✔B OH O OH CO2H ✗ C ✗ D
  86. 86. 2-hydroxy-3,3-dimethylpentanoic acid OH OH CO2H CO2H ✗ A OH ✔B OH O OH CO2H ✗ C ✗ D
  87. 87. 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
  88. 88. 2-hydroxy-3,3-dimethylpentanoic acid OH OH CO2H CO2H ✗ A OH ✔B OH O OH CO2H ✗ C ✗ D
  89. 89. 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
  90. 90. example3
  91. 91. 3-bromo-5-methylbenzoic acid O O OH HO Br Br A B O OH O OH Br Br C D
  92. 92. 3-bromo-5-methylbenzoic acid O O OH HO ✗ A Br Br ✗ B O OH O OH ✗ Br ✔ Br C D
  93. 93. 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
  94. 94. 3-bromo-5-methylbenzoic acid O O OH HO ✗ A Br Br ✗ B O OH O OH ✗ Br ✔ Br C D
  95. 95. 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
  96. 96. 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
  97. 97. 3-bromo-5-methylbenzoic acid O O OH HO ✗ A Br Br ✗ B O OH O OH ✗ Br ✔ Br C D
  98. 98. 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
  99. 99. 3-bromo-5-methylbenzoic acid O O OH HO ✗ A Br Br ✗ B O OH O OH ✗ Br ✔ Br C D
  100. 100. functional groups these are listed on pg 17
  101. 101. Read functionalgroups (Pg16-29) ©hebedesign@flickrI will not have time to go through these
  102. 102. alkanes H H C H H methane CH4 propane C3H8 CnH2n+2
  103. 103. alkanes H H C H H methane CH4 propane open chains (no C3H8 rings) have this general formula CnH2n+2
  104. 104. CnH2n+2 C6H2x6+2 H H H H H HH C6H14 HH H H H H H Reference
  105. 105. CnH2n+2 C6H12 ≠ CnH2n+2Functional groups
  106. 106. 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
  107. 107. alkanes H H C H H methane CH4 alkanes are tetrahedral in shape...we shall see why later propane C3H8 CnH2n+2
  108. 108. alkanes H H C H H methane CH4 alkanes are boring...normally fuels or solvents propane C3H8 CnH2n+2
  109. 109. structuralisomers pentane 2-methylbutane 2,2-dimethyl C5H12 C5H12 propane bp 36.2˚C bp 28˚C C5H12 bp 9.6˚C
  110. 110. 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
  111. 111. 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
  112. 112. alkenes H H H H ethene trigonal planar
  113. 113. alkenes more exciting as the double bond is reactive! H H H H ethene trigonal planar
  114. 114. alkenes means it is flat with three groups attached to central atom H H H H ethene trigonal planar
  115. 115. 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
  116. 116. 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
  117. 117. 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
  118. 118. 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
  119. 119. 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
  120. 120. alkenesin nature H3C CH3 CH3 H3C CH3 H3C(1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene α-pinene
  121. 121. 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
  122. 122. 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
  123. 123. 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
  124. 124. cyclic compounds cyclohexane benzene C6H12 C6H6
  125. 125. cyclic compounds some cyclic molecules are flat...because they have flat double bonds cyclohexane benzene C6H12 C6H6
  126. 126. cyclic compounds some look flat flat...but are not due to tetrahedral alkane structure (see lct 7) cyclohexane benzene C6H12 C6H6
  127. 127. 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
  128. 128. alcohols OH ethanol C2H6O
  129. 129. alcohols need OH attached to alkane (not alkene, alkyne or benzene) OH ethanol C2H6O
  130. 130. alcohols found in many biological systems... OH ethanol C2H6O
  131. 131. alcohols ...especially on Saturday nights... OH ethanol C2H6O
  132. 132. 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!
  133. 133. 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
  134. 134. 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
  135. 135. 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
  136. 136. 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
  137. 137. important terms & not just true of alcohols but allcommon mistakes functional groups X X X H H Hprimary secondary tertiary group group group
  138. 138. 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
  139. 139. 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
  140. 140. 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
  141. 141. 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
  142. 142. 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
  143. 143. 18-crown-6and potassiumcation
  144. 144. 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
  145. 145. 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
  146. 146. 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)
  147. 147. 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!
  148. 148. 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!
  149. 149. 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...
  150. 150. 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).
  151. 151. 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
  152. 152. 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
  153. 153. 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
  154. 154. 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)
  155. 155. 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)
  156. 156. 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)
  157. 157. the problemwith amines primary amine because only 1 primary amine carbon attached (1°) NH2 H3C OH CH3 O secondary position (2°)
  158. 158. 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°)
  159. 159. 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
  160. 160. 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
  161. 161. 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
  162. 162. 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
  163. 163. 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
  164. 164. 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
  165. 165. 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
  166. 166. 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
  167. 167. 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
  168. 168. how are functional groups related?
  169. 169. 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
  170. 170. Read this unit againLearn the functional groups ©sidewalk flying@flickr
  171. 171. 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
  172. 172. parts 3 & 4are combined word of warning...next 2 units will not be in the same order as study guide...
  173. 173. readPages 35, 37,41-42, 45-47 ©Fiduz@flickr

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