CHAPTER 13: Alcohols, Phenols, & Ethers 13.3 ALCOHOLS: PHYSICAL PROPERTIES 13.1 ALCOHOLS: NOMENCLATURE. Page H δ. water-like

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1 APTE 13: Alcohols, Phenols, & Ethers Identify alcohols, phenols. ethers, and thiols LASS GENEAL STUTUE PLAITY lassify alcohols as primary, secondary, or tertiary Understand how hydrogen bonding influences the physical properties of alcohols and ethers Predict how alcohol structure determines the products of dehydration and oxidation reactions Understand how thiols undergo oxidation and reaction with heavy metals Alcohols Phenols Ethers Thiols S polar polar nonpolar polar (weak) eview 4.11, 11.10, ALLS: PYSIAL PPETIES Polar compounds with the general structure - where is is any alkyl group and is is the hydroxyl group elationship to water: group gives alcohols water-like character Alcohols generally have higher bp s than similar alkanes Lower alcohols are 2 -soluble bp, 2 sol N Y YDGEN BNDING δ - Why aren t all alcohols water soluble? water-like NET: WATE-LIKE hydrocarbon-like but SMALL water-like hydrocarbon-like and LAGE IUPA 13.1 ALLS: NMENLATUE STEP 1 STEP 2 STEP 3 Identify the largest carbon chain or ring that includes the Add the -ol suffix (and any multiplier prefix) Number the main-chain atoms so the - gets the lowest possible number NET: YDABN-LIKE STEP 4 Identify branches Page 13-1

2 13.2 LASSIFIATIN F ALLS 2 Nº of GUPS LASS on - Primary 1 Secondary 2 2 Important ommon Names 2 Alkyl group name + alcohol LASS NAME METYL (wood) ALL Methanol ETYL (grain) ALL Ethanol Tertiary ISPPYL (rubbing) ALL 2-Propanol Important ommon Names 13.4 EATINS of ALLS LASS, 2 NAME ETYLENE GLYL 1,2-Ethanediol GLYEL 1,2,3-Propanetriol DEYDATIN emoval of of an an atom and the functional group as as 2 to to produce an an alkene equires acid catalyst (it s the reverse of hydration 12.3) Arrhenius Works because alcohols are not bases > Biochemically important: 2 enzyme 2 itric Acid cis-aconitic Acid XIDATIN emoval of of 2 atoms, converting - to to functional groups containing = (carbonyl) α [] -2 equires α-hydrogen ( ) Product type varies with alcohol class Page 13-2

3 ALLS 2 ALLS [] -2 ALDEYDE [] -2 KETNE [] ABXYLI AID 3 ALLS N EATIN 13.5 IMPTANT ALLS + DEYDATIN ALL ALKENE ALDEYDE KETNE ABXYLI AID [] XIDATIN 3 [] 2 No eaction FEMENTATIN Action of yeast, bacteria on sugars zymase ALKENE YDATIN Industrial processes 2 2 2, 325 catalyst 70 atm 2, PENLS ommon examples: ompounds that have the hydroxyl group bonded to to a benzene ring Phenols are weak acids: Na Na + Phenol arbolic acid Alcohols are not: N 3 Na EATIN ( ) 3 VITAMIN E (antioxidant) TYML (mint aroma) EXYLESINL (topical anesthetic) Page 13-3

13.7 ETES ompounds in in which an an atom is is bonded to to two hydrocarbon groups --, can be the same or different, can be alkyl or phenyl (or other substituted derivatives) 13.

4 13.7 ETES ompounds in in which an an atom is is bonded to to two hydrocarbon groups --, can be the same or different, can be alkyl or phenyl (or other substituted derivatives) 13.8 ETES: PPETIES Physical properties similar to alkanes (but note difference): Non-polar Melting points, boiling points related to molecular weight Soluble in hydrocarbon and alcohol solvents, insoluble in 2 Less dense than 2 bp, sol. N N hemical properties similar to alkanes (but note differences): Flammable elatively inert (but can form peroxides) 2 2 air 2 Ether molecules can t form -bonds with each other ommon Names: 13.9 TILS & DISULFIDES ETYLENE XIDE (sterilizing agent) EUGENL (oil of cloves) 2 2 F 2 F 2 lf ENFLUANE (ENTANE ) (general anesthetic) Non-polar = fat soluble 2 2 DIETYL ETE (solvent, general anesthetic) Thiols (mercaptans) are weakly polar compounds with the general structure -S where is is any alkyl or or aromatic group an an S is is the sulfhydryl (sulfanyl) group Less polar than alcohols (weaker -bonding) Nauseating odors (Eau de Skunk, etc.) S I didn t Major contributor do it! to sweat malodor Page 13-4

5 TILS: EMIAL PPETIES AIDITY S + K S K Weak acids XIDATIN-EDUTIN [] 2 S S S [] Weak bond DISULFIDE (determines protein structure) SALT FMATIN 2 S + M 2+ ( S ) 2 M 2+ eavy Metals: g 2+, Pb 2+ eavy metal toxicity: Salt formation destroys S, S S structures in enzymes, so Enzymes deactivated, leading to Unfortunate outcomes Page 13-5

Chapter 14 Organic Compounds That Contain Oxygen, Halogen, or Sulfur

Chapter 14 Organic Compounds That Contain Oxygen, Halogen, or Sulfur Based on Material Prepared by Andrea D. Leonard University of Louisiana at Lafayette Copyright The McGraw-Hill Companies, Inc. Permission