Williamson ether synthesis reaction of metal alkoxides with alkyl halides or tosylates to give ethers. The williamson ether synthesis, alkoxymercuration of alkenes, and also the acid catalyzed substitution. Objectives alcohols, phenols and ethers are the basic compounds for the formation of detergents, antiseptics and fragrances, respectively. Naoch 3 typical ethers are unreactive towards nucleophiles epoxides are severely strained, they therefore react with nucleophiles in order to open the ring and release the strain since this is a version of an sn2 reaction, reaction typically occurs at the less substituted carbon atom 2. The alcohol produced reacts to generate a second molecule of alkyl halide. Reactions of alcohols, ethers, epoxides, amine, and. This low reactivity makes them useful as solvents, e. Another method is the williamson ether synthesis, which involves a reaction between a metal alkoxide and an alkyl halide. Alcohols, ethers, epoxides, sulfides organic chemistry.
Alcohols, ethers, epoxides, sulfides organic chemistry khan. Epoxides are more reactive than simple ethers due to the inherent ring strain and react with nucleophiles resulting in ring opening. Inert to a wide range of reaction conditions good solvents synthesis of ethers. Reaction of metal alkoxides with alkyl halides or tosylates to. If the epoxide reacts with a biological macromolecule, the result is potentially devastating. Ether c from problem 26 can also be prepared from an alkene and an alcohol, draw these two. We also acknowledge previous national science foundation support under grant numbers 1246120, 1525057. Alcohols, ether, and epoxides are 3 functional groups that contain c. Remember the approximate pka values for alcohols, water, and hydronium ion. Physical properties of ethers the oh group of alcohols act as both an. Because the o atom is much more electronegative than carbon or hydrogen, the co and oh bonds are all polar. Reactions of alcohols, ethers, epoxides, amines, and thiols chapter 11 reactions of alcohols, ethers, epoxides, amines, and thiols paula yurkanis bruice university of california, santa barbara protonating an amine does not. These processes were carried out at room temperature and rely on the usefulness of commercial copper tetrafluoroborate as catalyst.
Physical properties of ethers the oh group of alcohols act as both an hbond. Part a the focus of this chapter can be thought of as the organic version of water. Ethers ethers are organic compounds with two alkyl groups. Reactions of ethers although ethers are relatively inert toward reaction, they usually show good solvent properties for many nonpolar organic compounds. Epoxides that are formed in the liver by cytochrome p450 undergo ringopening reactions. Alcohol and thiol groups are important functional groups for applications ranging from enzyme reactions to making flexible contact lenses. Ethers ethers are organic compounds with two alkyl groups attached.
We also acknowledge previous national science foundation support under grant numbers 1246120, 1525057, and 14739. In chapter 9, we take the principles learned in chapters 7 and 8 about leaving groups, nucleo philes, and bases, and apply them to alcohols, ethers, and epoxides, three new functional groups that contain polar c o bonds. In contrast to alcohols, ethers are fairly unreactive except to very strong acids such as hi or hbr. Alkoxides are prepared by the reaction of an alcohol with a strong base such as sodium hydride nah. Ethers have two hydrocarbon groups groups bonded to an oxygen atom. Janice gorzynski smith university of hawaii chapter 9. Aldehydes and ketones undergo reactions in which and alcohol molecule is added across the carbonyl group co double bond. Boiling point of ethers is lower than alcohols since there is no hydrogen bonding. Science organic chemistry alcohols, ethers, epoxides. Ppt ethers powerpoint presentation free to download. Dimethyl ether and ethyl methyl ether is gas at ordinary temperature while the other lower homologues of ethers are colourless liquid with characteristic ether smell. Module 5 alcohols, amines, ethers and epoxides lecture 10. Alcohols are capable of intermolecular hydrogen bonding. In general, the co bonds of ethers have low reactivity.
Alcohols contain a hydroxy group oh bonded to an sp3 hybridized carbon. Their inert nature and the fact that most organic compounds are ether soluble makes them excellent solvents for organic reactions. Describe the physical properties of alcohols, amines and ethers. Learn vocabulary, terms, and more with flashcards, games, and other study tools. Then we will be ready to learn about some reactions that involve alcohols, ethers, epoxides, thiols, and sulfides as both reactants and products. The libretexts libraries are powered by mindtouch and are supported by the department of education open textbook pilot project, the uc davis office of the provost, the uc davis library, the california state university affordable learning solutions program, and merlot. Alcohols, ethers and phenols article pdf available in journal of the chemical society perkin transactions 1 116. Reactions of alcohols, amines, ethers, and epoxides learning objectives. When h 2o has one or both of its hydrogens replaced by an r group we get alcohols and ethers. Given the starting materials and reaction conditions, predict the products of the following reactions involving alcohols and ethers. After three alkene units have added the intermediate is treated with basic hydrogen peroxide to form the alcohol. Primary ether or methyl alkyl halide alkoxide nucleophile bond formed bond broken note that c. Nomenclature of ethers, epoxides, and sulfides please read 16.
Using any of the above reactions, propose syntheses of compounds that can be made using alcohols as starting materials or intermediates. They do not react with metallic sodium unlike alcohols. Nomenclature and preparation of epoxides video khan. Provide the correct common and iupac name of the following alcohols. Formation of secondary alcohols reaction of an aldehyde with a grignard reagent generates a secondary alcohol. Ethers, epoxides, glycols, and sulfides solutions to intext problems 11.
Solvents is usually the conjugate acid of the alkoxide. The naming of epoxides can either be from the starting alkene used to. Draw the electron arrow pushing mechanism for the formation of diethyl ether in the previous problem. Alcohols, ethers and epoxides complete the equations for the following reactions.
Ethers, epoxides, sulfides ethers are much less reactive than alcohols but epoxides threemembered ring ethers are very reactive as we saw in the last chapter. This organic chemistry video describes the intermolecular forces and physical properties of alcohols, ethers, and epoxides. Ethers as solvents ethers are relatively inert compounds. Structure and bonding in ethers and epoxides the ether oxygen is sp3hybridized and tetrahedral. Show all organic products if two or more products form, indicate. Synthesizing ethers and epoxides as mentioned previously, we have already studied the acidcatalyzed synthesis of ethers from alcohols. Provide both iupac and common when applicable names for alcohols and ethers. Be able to predict the relative acidities of phenols, alcohols, and thiols. Revision notes on alcohols, phenols and ether askiitians. Using similar reactions, tetrahydropyranyl ethers are used as protective groups for alcohols. The boron atom adds to the least substituted carbon atom. The chemistry of ethers, epoxides, glycols, and sulfides. The oxygen of the epoxide comes from molecular oxygen. They do no usually react with dilute acids or bases or common oxidizing and reducing agents.
The bond angle around the o atom in an alcohol or ether is similar to the tetrahedral bond angle of 109. Often, mercury trifluoroacetate hgococf 3 2 is used as a catalyst for the reaction generating an ether with markovnikov regiochemistry. Nomenclature in substitutive iupac nomenclature ethers are named as alkoxy derivative derivatives of alkanes. This strong dissolving power coupled with low reactivity makes ethers good solvents in which to run reactions. Thus, alcohols are more polar than ethers and epoxides. The reaction stops at the phenol stage since the sp2 carbon of the coh bond does not allow the required s n 1 or s n 2 reactions to generate the second molecule of aryl halide. Unlike straight chain ethers, epoxides react readily with good nucleophiles. Alcohols, ethers, and epoxides exhibit dipoledipole interactions because they have a bent structure with two polar bonds. Ethers are inert and make excellent solvents for organic reactions. Mgbr o oh ether o oh lah ether oh grignard reaction.
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