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Isomers of C 5 H 12 O

Isomers of C 5 H 12 O. by Dr.Gergens. Draw all fourteen isomers of C 5 H 12 O Goals: draw all isomers & identify functional groups; alcohols (eight) & ethers (six) identify methyl, primary, secondary & tertiary carbon centers define a heteroatom and give examples

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Isomers of C 5 H 12 O

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  1. Isomers of C5H12O by Dr.Gergens

  2. Draw all fourteen isomers of C5H12O • Goals: • draw all isomers & identify functional groups; alcohols (eight) & ethers (six) • identify methyl, primary, secondary & tertiary carbon centers • define a heteroatom and give examples • identify alcohol type as primary, secondary & tertiary alcohols • identify, name & draw branch names for • methyl • ethyl • n-propyl • isopropyl • n-butyl • sec-butyl • iso-butyl • t-butyl • • amyl • isoamyl • sec-amyl • • sec-isoamyl • • neopentyl • • tert-amyl • • give abbreviations for branch names • Me, Et, nPr, iPr, nBu, sec-Bu, iBu, t-Bu • give common and IUPAC to ethers and alcohols • identify chiral centers • identify planes of symmetry

  3. The fourteen isomers of C5H12O - alcohols (eight)

  4. The fourteen isomers of C5H12O - ethers (six)

  5. The fourteen isomers of C5H12O - carbon centers Me Me Me CH3 N CH3 O CH3 F 1° C C 2° C C C C C C C 3° a CH3 bonded to a heteroatom is a methyl group a heteroatom is an atom other than carbon a carbon bonded to only one carbon is 1° primary a carbon bound to two carbons is 2° secondary a carbon bound to three carbons is 3° tertiary

  6. The fourteen isomers of C5H12O - ethers (six) 1° primary carbons 1° 1° 1° Me 1° 1° C C Me 1° 1° 1° 1° 1° 1° 1° Me 1° 1° 1° 1° 1° Me 1° 1° Me CH3 O

  7. The fourteen isomers of C5H12O - ethers (six) 2° secondary carbons 2° C C C 2° 2° 2° 2° 2° 2°

  8. The fourteen isomers of C5H12O - ethers (six) 3° tertiary carbons C C C C 3° 3° 3°

  9. The fourteen isomers of C5H12O - alcohols (eight) 1° primary carbons 1° 1° 1° 1° 1° 1° 1° 1° 1° 1° 1° 1° 1° 1° C C 1° 1° 1° 1° 1° 1° 1° 1° 1°

  10. The fourteen isomers of C5H12O - alcohols (eight) 3° tertiary carbons C C C C 3° 3° 3° 3° 3°

  11. The fourteen isomers of C5H12O - alcohols (eight) C C C C 4° C 4° quaternary 4°

  12. The fourteen isomers of C5H12O - heteroatom centers Me Me Me CH3 N CH3 O CH3 F a CH3methyl group bonded to a heteroatom is a methyl group a heteroatom is an atom other than carbon 1° 1° 1° C C C C C C F OH NH2 H C C C N N C C 3° 2° a heteroatom bonded to a 1° primary center is considered primary a nitrogen heteroatom bonded to two carbons as a secondary amine a nitrogen heteroatom bonded to three carbons as a 3° tertiary amine

  13. The fourteen isomers of C5H12O - heteroatom centers Me Me Me CH3 N CH3 O CH3 F a CH3 bonded to a heteroatom is a methyl group a heteroatom is an atom other than carbon C C C OH 1° 3° C C OH C C C C OH 2° a hydroxyl bonded to a primary carbon center is a 1° alcohol a hydroxyl bonded to secondary carbon center is a 2° alcohol a hydroxyl bonded to tertiary carbon center is a 3° alcohol

  14. The fourteen isomers of C5H12O - 1°, 2° & 3° alcohols C C C C 3° C 1° C C 3° alcohol C 1° alcohol 2° alcohol C C C C C C C 2° C C C C C 1° 1° alcohol C C C C 1° C C C C 2° alcohol 1° alcohol 2° alcohol C C 2° C C 1° C C C C C 2° C C C 1° alcohol

  15. The fourteen isomers of C5H12O - ethers (six) - branch names methyl methyl methyl methyl C C C C

  16. The fourteen isomers of C5H12O - ethers (six) - branch names C C ethyl C C ethyl

  17. The fourteen isomers of C5H12O - ethers (six) - branch names C C C isopropyl n-propyl C C 2° C 1°

  18. The fourteen isomers of C5H12O - ethers (six) - branch names sec-butyl C C C C C C C C n-butyl 2° 1°

  19. The fourteen isomers of C5H12O - ethers (six) - branch names t-butyl isobutyl C C C C C C C C 3° 3° C C C C C 1° C 3° 1° C C

  20. The fourteen isomers of C5H12O - branch name abbreviations methyl, Me sec-butyl sec-Bu t-butyl tBu isobutyl, iBu methyl, Me ethyl, Et methyl, Me isopropyl iPr n-butyl nBu n-propyl, nPr methyl,Me ethyl, Et

  21. The fourteen isomers of C5H12O - additionalbranch names C C C C 3° C C C tert-amyl or t-pentyl 3° C neopentyl sec-isoamyl C C C C C C 2° C C C C C 1° C sec-pentyl or sec-amyl isoamyl 1° C n-pentyl or n-amyl sec-isopentyl or isopentyl or C C C C C C 2° C C C

  22. The fourteen isomers of C5H12O - commonnaming of ethers t-butyl methyl ether isobutyl methyl ether sec-butyl methyl ether ethyl isopropyl ether n-butyl methyl ether ethyl n-propyl ether KNOW these branch names used in these commonly named ethers. Simple branch name are also used in naming alcohols and alkyl halides.

  23. The fourteen isomers of C5H12O - IUPACnaming 2,2-dimethyl-1-propanol 1,1-dimethyl-1-propanol 3-methyl-2-butanol 2-methyl-1-butanol 3-methyl-1-butanol 3-pentanol 2-pentanol 1-pentanol KNOW IUPAC traditional naming rules in naming alcohols, ALWAYS 1 & 2: 1) circle the longest continuous chain & 2) start numbering to the closest hydroxyl

  24. The fourteen isomers of C5H12O - IUPACnaming 1,1-dimethyl-1-methoxyethane 2-methyl-1-methoxypropane 2-methoxybutane 2-ethoxy-2-propane 1-methoxybutane 1-ethoxypropane KNOW IUPAC traditional naming rules, ALWAYS 1 & 2: 1) circle the longest continuous chain & 2) number to the closest branch

  25. The fourteen isomers of C5H12O - chiral centers, asymmetric centers

  26. The fourteen isomers of C5H12O - chiral centers, asymmetric centers

  27. Identifying Chiral Centers by Dr.Gergens

  28. Not chiral-molecule has a plane of symmetery Not chiral-molecule has a plane of symmetery Not chiral-molecule has a plane of symmetery Chiral-molecule is asymmeteric

  29. Not chiral-molecule has a plane of symmetery Not chiral-molecule has a plane of symmetery Chiral-molecule is asymmeteric This carbon center is NOT chiral

  30. Not chiral-molecule has a plane of symmetery This carbon center is NOT chiral This carbon center is NOT chiral

  31. This carbon center is NOT chiral This carbon center is chiral This carbon center is chiral This carbon center is chiral This carbon center is chiral

  32. This carbon center is NOT chiral This carbon center is chiral This carbon center is chiral

  33. This carbon center is NOT chiral This carbon center is NOT chiral This carbon center is NOT chiral This carbon center is NOT chiral

  34. This carbon center is chiral This carbon center is chiral This carbon center is chiral This carbon center is chiral

  35. This carbon center is chiral This carbon center is chiral This carbon center is chiral This carbon center is chiral

  36. This carbon center is NOT chiral These carbons center are NOT chiral These carbons center are NOT chiral This carbon center is NOT chiral This carbon center is chiral These carbons center are chiral These carbons center are chiral This carbon center is chiral

  37. The fourteen isomers of C5H12O - alcohols (eight) - branch names sec-pentyl or sec-amyl 1° C n-pentyl or n-amyl C C C C C C 2° C C C

  38. The fourteen isomers of C5H12O - alcohols (eight) - branch names sec-isoamyl C C C C 2° C C C C C 1° C isoamyl sec-isopentyl or isopentyl or

  39. The fourteen isomers of C5H12O - alcohols (eight) - branch names C C C C 3° C C C t-tert-amyl or t-pentyl 3° C neopentyl C C

  40. The fourteen isomers of C5H12O - alcohols (eight) - branch names C C C C 3° C C C t-tert-amyl or t-pentyl 3° C neopentyl sec-isoamyl C C C C C C 2° C C C C C 1° C sec-pentyl or sec-amyl isoamyl 1° C n-pentyl or n-amyl sec-isopentyl or isopentyl or C C C C C C 2° C C C

  41. The fourteen isomers of C5H12O - ethers (six) - branch names methyl sec-butyl t-butyl methyl isobutyl ethyl methyl isopropyl n-butyl methyl n-propyl ethyl

  42. The fourteen isomers of C5H12O - ethers (six) 1° 1° methyl 1° 1° 1° 1° sec-butyl t-butyl methyl isobutyl 1° 1° 1° 1° 1° 1° 1° 1° ethyl methyl 1° isopropyl 1° 1° 1° 1° 1° 1° 1° n-butyl methyl n-propyl ethyl 3° 3° 2° 2° 2° 2° 2° 2°

  43. The fourteen isomers of C5H12O - alcohols (eight) 1° 1° 1° 1° 1° t-tert-amyl t-pentyl neopentyl sec-isoamyl 1° 1° 1° 1° 1° 1° 1° 1° 1° 1° 1° 1° sec-amyl isopentyl 1° 1° 1° 1° 1° n-pentyl 3° 4° 2° 3° 2° 3° 2° 2° 3° 2° 2° 2° 2° 2° 2° 2° 2° 2°

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