lecture 10 - Examples Alcohols and Thiols Chapter 10...

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Alcohols Alcohols and and Thiols Thiols Chapter 10 Chapter 10 Examples Examples Structure Structure - Alcohols Alcohols ± The functional group of an alcohol is an -OH group bonded to an sp 3 hybridized carbon bond angles about the hydroxyl oxygen atom are approximately 109.5° 108.9° O C H H H H Structure - Alcohols Alcohols ± Oxygen is sp 3 hybridized two sp 3 hybrid orbitals form sigma bonds to carbon and hydrogen the remaining two sp 3 hybrid orbitals each contain an unshared pair of electrons 108.9° O C H H H H Nomenclature Nomenclature -Alcohols Alcohols ± IUPAC names the parent chain is the longest chain that contains the OH group number the parent chain to give the OH group the lowest possible number change the suffix -e to -ol ol ± Common names name the alkyl group bonded to oxygen followed by the word alcohol alcohol
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Nomenclature Nomenclature -Alcohols Alcohols ± Examples 2-Methyl-2-propanol (tert - Butyl alcohol) OH 1-Propanol (Propyl alcohol) OH 2-Propanol (Isopropyl alcohol) OH 1-Butanol (Butyl alcohol) OH 2-Butanol ( sec- Butyl alcohol) OH 2-Methyl-1-propanol (Isobutyl alcohol) OH Nomenclature Nomenclature -Alcohols Alcohols ± Examples OH Bicyclo[4.4.0]decan-3-ol 8 10 9 1 2 3 4 5 7 6 Numbering of the bicyclic ring takes precedence over the location of -OH cis- 3-Methylcyclohexanol OH 1 4 5 2 3 6 Nomenclature of Alcohols ± Compounds containing more than one OH group are named diols, triols, etc. CH 3 CHCH 2 HO OH CH 2 CH 2 OH OH CH 2 CHCH 2 HO HO OH 1,2-Ethanediol (Ethylene glycol) 1,2-Propanediol (Propylene glycol) 1,2,3-Propanetriol (Glycerol, Glycerine) Practice Answer: 4-methyl-2-pentanol, (1R,2R-2-methylcyclohexanol; bicyclo[2.2.1]-1-heptanol Classification of Alcohols p. 387 Compounds Containing Two hydroxyl Groups glycols
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Nomenclature of Alcohols Nomenclature of Alcohols ± Unsaturated alcohols show the double bond by changing the infix from -an- to -en en - show the the OH group by the suffix -ol ol number the chain to give the OH the lower number 1 23 45 6 ( E )-2-Hexene-1-ol ( trans-2 -Hexen-1-ol) HO Practice Physical Properties ± Alcohols are polar compounds they interact with themselves and with other polar compounds by dipole-dipole interactions ± Dipole Dipole -dipole interaction: dipole interaction: the attraction between the positive end of one dipole and the negative end of another O H H H C H δ + - Physical Properties Physical Properties ± Hydrogen bonding Hydrogen bonding: when the positive end of one dipole is a H bonded to F, O, or N (atoms of high electronegativity) and the other end is F, O, or N the strength of hydrogen bonding in water is approximately 21 kJ (5 kcal)/mol hydrogen bonds are considerably weaker than covalent bonds nonetheless, they can have a significant effect on physical properties Hydrogen Bonding Hydrogen Bonding Physical Properties Physical Properties ± Ethanol and dimethyl ether are constitutional isomers.
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lecture 10 - Examples Alcohols and Thiols Chapter 10...

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