Notes chapter 03
- 1. Chapter 3 Notes Trial version of Okdo Document Converter Professional. http://www.okdosoft.com CHEM 2353 Fundamentals of Organic Chemistry Chapter Chapter Alcohols, Phenols, 3 and Ethers Organic and Biochemistry for Today (4 th ed.) Spencer L. Seager / Michael R. Slabaugh Mr. Kevin A. Boudreaux Angelo State University www.angelo.edu/faculty/kboudrea 1 Introduction • In this chapter, we will start looking at organic molecules that incorporate C—O bonds. • The alcohol, phenol, and ether functional groups are found in a number of important naturally occurring molecules: CH 3CH 2OH Ethanol OH CH 3CH 2OCH 2 CH3 HO Diethyl ether Menthol Cholesterol 2
- 2. Chapter 3 Notes Alcohols 3 The Hydroxy (—OH) Functional Group • The hydroxyl group (—OH) is found in the alcohol and phenol functional groups. - in alcohols, a hydroxyl group is connected to a carbon atom. - in phenols, —OH is connected to a benzene ring. (The "parent" molecule of this class is also named phenol: PhOH or C 6H 5OH.) • When two carbon groups are connected by single bonds to an oxygen, this is classified as the ether functional group. R OH R O R' OH an ether an alcohol a phenol 4
- 3. Chapter 3 Notes Where Does the Word "Alcohol" Come From? • The word "alcohol" comes from the Arabic term al kohl meaning "the fine powder." Originally, this referred to an antimony sulfide compound used for eye shadow, which was ground up to form a fine powder, but then later came to refer to any finely divided powder. In the Middle Ages, this term came to mean the "essence" of anything. • When the Europeans took up alchemy in the Middle Ages, they referred to vapors from evaporating or boiling compounds as "spirits," since they did not believe them to be material in the same sense that solids and liquids were. Alchemists began referring to "spirits of wine," and since an alcohol when it boils away seems to powder away to nothing, they also began to refer to "alcohol of wine" and then simply "alcohol". 5 Some Common Alcohols CH 3OH CH 3CH 2OH methanol ethanol methyl alcohol ethyl alcohol (wood alcohol) (grain alcohol) ("methy" = wine, "hule" = wood) The acohol of alcoholic beverages; the Found in wood smoke; contributes to the fermentation of honey, grain, or fruit juices to bouqet of new wine; metabolized in the body yield beers and wines was probably the first to formaldehyde and formic acid, and can chemical reaction to be discovered; metabolized cause blindness or death (> 50 mL) in the body to produce acetaldehyde CH 3CH 2CH OH 2OH 1-propanol CH 3CHCH3 n-propyl alcohol 2-propanol isopropyl alcohol Rubbing alcohol is 70% isopropyl alcohol and 30% water 6