Chemistry 2100 Lecture 4

ALCOHOLSETHERSTHIOLS

thiol / mercaptan (sulfhydryl) alcoholether

Common Nomenclature alkyl "alcohol" dialkyl "ether" IUPAC Nomenclature "e" "ol" locator numbers

Alcohols Alcohol:OH (hydroxyl) group Alcohol: A compound that contains an -OH (hydroxyl) group bonded to a tetrahedral carbon. –Methanol, CH 3 OH, is the simplest alcohol. Nomenclature 1. Select the longest carbon chain that contains the -OH group as the parent alkane and number it from the end that gives the -OH the lower number. eol 2. Change the ending of the parent alkane from -e to -ol and use a number to show the location of the -OH group; for cyclic alcohols, the carbon bearing the -OH group is carbon Name and number substituents and list them in alphabetical order.

Nomenclature diol triol –In the IUPAC system, a compound containing two hydroxyl groups is named as a diol, one containing three hydroxyl groups as a triol, and so forth. –IUPAC names for diols, triols, and so on retain the final "-e" in the name of the parent alkane. glycols –We commonly refer to compounds containing two hydroxyl groups on adjacent carbons as glycols.

Physical Properties Alcohols are polar molecules. –The C-O and O-H bonds are both polar covalent.

Physical Properties In the liquid state, alcohols associate by hydrogen bonding.

CH 3 OH 65°CH 3 CH 2 CH 2 OH 97° CH 3 CH 3 -88°CH 3 CH 2 CH 2 CH 3 0° CH 3 Cl -24°CH 3 CH 2 CH 2 Cl 46° PhOH 182°CH 3 CH 2 CH 2 CH 2 OH 118° PhCH 3 110°(CH 3 ) 2 CHCH 2 OH 108° PhCl 132°(CH 3 ) 3 COH 83° boiling points (°C)

solubility (g / 100 mL H 2 O) ∞ ∞ 3.6 CH 3 CH 2 OH CH 3 CH 2 CH 2 OH CH 3 CH 2 CH 2 CH 2 OH CH 3 CH 2 CH 2 CH 2 CH 2 OH CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 OH CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 OH CH 3 CH 2 OCH 2 CH 3 (CH 3 ) 2 CHCH 2 OH (CH 3 ) 3 COH C 6 H 11 OH

zymase sucrose ethanol Preparing Alcohols Fermentation Alkene Hydration H HH H H HH H

Dehydration

Oxidation of Alcohols (1°) (2°)

Ethers

Common Nomenclature dialkyl "ether" "alkoxy" IUPAC Nomenclature

(diethyl) ether bp 36°C 7.8 g/100 mL 1-butanol bp 118°C 8.3 g/100 mL pentane bp 36°C

Anesthetics

Thiols / Mercaptans

Naming thiols Alkane + thiol 1-propanethiol2-propene-1-thiol

CH 3 CH 2 OH (bp 78°C)CH 3 OCH 3 (bp -24°C) CH 3 CH 2 SH (bp 35°C)CH 3 SCH 3 (bp 37°C)

sulfoxidesulfide (thioether) sulfone Oxidation

cysteine

 -helix

 -pleated sheet

 -helix  -pleated sheet

salt bridge  -helix  -pleated sheet

hydrogen bond salt bridge  -helix  -pleated sheet

hydrogen bond hydrogen bond salt bridge  -helix  -pleated sheet

hydrogen bond hydrogen bond salt bridge hydrophilic interaction to water  -helix  -pleated sheet

hydrophobic interaction hydrogen bond hydrogen bond salt bridge hydrophilic interaction to water  -helix  -pleated sheet

hydrophobic interaction hydrogen bond hydrogen bond salt bridge hydrophilic interaction to water  -helix  -pleated sheet

hydrophobic interaction disulfide bond hydrogen bond hydrogen bond salt bridge hydrophilic interaction to water  -helix  -pleated sheet