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Alcohols, Phenols, Ethers, Aldehydes, and Ketones
Greg Evanson 7 March 2013
Transcript of Alcohols, Phenols, Ethers, Aldehydes, and Ketones
Alcohols, Phenols, Ethers, Aldehydes, and Ketones 12.1 - Alcohols and Phenols Rules for Naming Alcohols 12.2 - Names of Alcohols and Phenols Alcohols with short carbon chains are soluble in water, as the chains get longer they become less soluble. 12.3 - Properties of Alcohols and Phenols Just as hydrocarbons can undergo combustion reactions, so can alcohols. 12.4 - Reactions of Alcohols Many important organic compounds have a carbonyl group, a carbon joined to an oxygen with a double bond. 12.7 - Properties of Aldehydes and Ketones Phenols - the hydroxyl group is attached to a carbon atom of a benzene ring Formation of Alcohols Alkane can be produced by the hydration of an alkene in the presence of an acid. Ethyl alcohol is most often prepared by fermentation of sugars. Classification
of Alcohols Alcohols are classified based on the number of alkyl groups attached to the carbon atom bonded to the -OH. primary (1 ) alcohol - one alkyl group is attached o secondary (2 ) alcohol - two alkyl groups are attached tertiary (3 ) alcohol - three alkyl groups are attached o o also considered a primary alcohol select the parent chain containing the -OH group and replace the e in its name with an ol. ex. butane, butanol
number the parent chain starting with the end closest to the -OH
give the number for the position of the -OH in front of the parent name
give the name and numbers of any substituents Cycloalkanols are cyclic alcohols, numbered with the carbon atom bonded to the -OH as 1. 2 -OH = diol
3 -OH =triol alcohols with 1-4 C are very soluble
alcohols 5-7 C are much less soluble
alcohols with8 C are insoluble In shorter chains the electronegative oxygen makes the functional group very polar, in longer chains they behave more like the corresponding alkane. Properties of Phenols Phenols behave differently in water than alkyl alcohols.Phenol can slightly ionize to make a weak acid, used to be called carbolic acid. Thiols Family of sulfur containing organic compounds, but have an -SH functional group instead of -OH. Named by adding thiol to the name of the longest chain attached to the -SH functional group. used to be called mercaptan Thiols have strong, disagreeable odors. energy + + Alcohols can also undergo dehydration and oxidation reactions. Dehydration of Alcohols The addition of water to alkenes produces alcohol, so in a reverse reaction most alcohols can dehydrate when heated with an acid catalyst. During dehydration an H- and -OH are removed from adjacent carbon atoms of the same alcohol. A double bond then forms between those two carbons. The dehydration of a secondary alcohol can form a major and a minor product. For the major product to be produced the H- is removed from the C with the smallest number of hydrogen atoms. Oxidation of Alcohols In oxidation reactions hydrogen atoms are lost or oxygen atoms are gained by the alcohol. The level or oxidation is determined by the amount of multiple bonds or bonds to atoms other than C and H. The oxidation on primary alcohols to aldehydes and secondary alcohols to ketones both occurs because of the loss of H. Tertiary alcohols normally don't oxidize. All oxidized alcohols contain a C-O double bond. Oxidation of Primary Alcohols One H is removed from the carbon attached to the -OH, and the other H is taken from the -OH itself.This reaction produces an aldehyde and water. Aldehydes can further oxidize to form caboxylic acids. Oxidation of Secondary Alcohols The process is similar to that of the primary alcohol. The result is a C-O double bond attached to alkyl groups on both sides and water. 12.5 - Ether Contains an O attached by single bonds to two alkyl or aromatic groups. Dimethyl ether Ethyl methyl
ether Methyl phenyl
ether The general formula is: R O R 1 2 Formation of Ethers Formed from primary alcohols when dehydration occurs at lower temperatures in the presence of an acid catalyst. Naming Ethers Simple ethers are usually called by their common names.the groups attached to the oxygen are listed in alphabetical order followed by the name ether. IUPAC Naming Rules Find the longest carbon chain and select its alkane name.
Name the shorter carbon group and the oxygen as an alkoxy group, then number the parent chain starting from the alkoxy group.
Give the location of the alkoxy group on the parent chain. Solubility and Uses of Ethers less soluble in water than alcohols but more soluble than alkanes Ether is a very useful solvent which does not react with the substanceit dissolves.
Ether vapors however are highly flammable and react explosively with oxygen in the air. In aldehydes the carbonyl carbon is attached to a hydrogen atom. In ketones the carbonyl group is bonded to two alkyl or aromtic groups. Names of Aldehydes In the IUPAC system, replace the -e in the longest chain with -al. The the first four aldehydes have common names beginning with the prefixes form, acet, propion, and butyr followed by the word aldehyde. used in manufacturing of paper, insulation, cosmetics, and some shampoos carbonyl group is always the first carbon, substituents can be indicated by #'s or lowercase Greek letters Names of Ketones In the IUPAC system the -e is replaced with -one. The chain is numbered starting at the end containing the carbonyl group. If there are alkyl groups they are listed alphabetically, followed by ketone. the carbonyl bond is strongly polar, this bond determines how the aldehydes and ketones behave Compounds with 1-4 C are soluble in water. The carbonyl group makes ketones good solvents for many organic compounds. Because aldehydes oxidize easily and ketones do not, Tollens' Test can be performed to distinguish the two. Aldehydes and Ketones can be converted back into alcohols through a reduction reaction. A reduction reaction causes a hydrogen to be added and/or an oxygen to be lost.