Download Organic Compounds: Alcohols, Phenols, Thiols, Ethers, Aldehydes, and Ketones - Prof. Roman and more Study notes Biology in PDF only on Docsity! Alcohols 1. Addition of –OH group to alkene produces alcohol ethanol 2-propanol Alcohol Nomenclature 1. Longest C chain with -OH is parent chain 2. Replace -e in parent name with -ol 3. End nearest -OH is C1 4. Number & name side groups appropriately Cycloalcohol Examples
a
cyclohexanol om
CH,
3-methylcyclohexanol
Diols & Triols 1. Diol- alcohol with 2 -OH groups 1,2-ethanediol 2. Triol- alcohol with 3 -OH groups 1,2,3-propanetriol (glycerol, glycerine) Alcohol Solubility 1. -OH group is polar 2. Short chain alcohols are water soluble, methanol to n-butanol 3. Long chain alcohols are water insoluble, n-pentanol on up Phenol Properties 1. Ionizes in H2O as weak acid 2. Conc phenol is corrosive, weak sol’ns were used antiseptically Thiols 1. Addition of -SH group to organic compound produces thiol 2. Similar solubilty as alcohols 3. Many have strong odors 4. Ethanethiol added to methane for detection Thiol Nomenclature 1. Longest chain with -SH is parent chain 2. Number parent chain to give lowest value to C with -SH group 3. Mercaptan- older term for thiol Naming Ethers, IUPAC 1. Name shorter chain, replace -ane suffix with -oxy 2. Write name of longer chain 3. Number from short to long chain starting at long chain 4. Write number of -oxy carbon followed by dash and name Naming Ethers, common 1. Used for many simple ethers 2. Alkyl or aromatic in alphabetical order followed by ether Ether Examples 1 1-methoxypropane (1-methyl propyl ether) 2-methoxybutane (2-methyl butyl ether) Alcohol Reactions 1. Combustion 2. Dehydration Alcohol Combustion 1. Alcohols combine with O2 & combust, needs activation energy Alcohol Dehydration , ##T 1. Produces alkene + H2O, high heat & H+ catalyst Aldehyde Examples
T i
one Rem Ones
methanal ethanal
(formaldehyde) 0 (acetaldehyde)
II
Ota a
phenylmethanal
(benzaldehyde)
Aldehyde Nomenclature 1. Longest C chain with carbonyl group is parent chain, change -e to -al 2. C with aldehyde group is C1 3. Common names are often used for unbranched aldehydes with one to four carbons Aldehyde Nomenclature Examples
OH 0
ae ooo a
v
2-hydroxypropanal *
Cl C-H
4-chlorobenzanal
(4-chlorobenzaldehyde)
Ketone Nomenclature Examples
CH; O
oF eter eer h
4 perl -2-pentanone
ri i
CH,CH,CH,CCH,
5-chloro-2-pentanone
Aldehyde & Ketone Solubility 1. Carbonyl group is polar 2. Short chain aldehydes & ketones, C1 to C4, are water soluble Oxidation & Reduction 1. Oxidation- Always loss of e- by loss of 2H atoms &/or gain of O atom 2. Reduction- Always gain of e- by gain of 2H atoms &/or loss of O atom 1o Alcohol Oxidation 1. Oxidation of 1o alcohol first produces aldehyde ethanol oxidizing ethanal agent (acetaldehyde) Aldehyde Oxidation 1. Oxidation of aldehyde produces carboxylic acid methanal oxidizing methanoic acid (formaldehyde) agent (formic acid) 2o Alcohol Oxidation 1. Oxidation of 2o alcohol produces ketone 2-propanol oxidizing propanone agent (acetone) (dimethyl ketone) 2. 3o alcohols do not oxidize Hemiacetal 1. Alcohol and aldehyde produce hemiacetal 2. Left rxn, so hemiacetal is hard to obtain ethanal methanol hemiacetal Hemiketal 1. Alcohol and ketone produce hemiketal 2. Left rxn, so hemiketal is hard to obtain propanone methanol hemiketal
