CHEM 210 [CHAPTER 10: REACTIONS AND SYNTHESIS 10 Fall 2016 Chapter 11: Alcohols, Ethers and Epoxides - KEY Complete the equations for the following reactions. dehydration, oxidation, and esterification. Describe the result of the oxidation of a primary alcohol. (Ethers are discussed in elsewhere) Thus, depending on conditions, one can prepare either alkenes or ethers by the dehydration of alcohols. Chemical reactions in alcohols occur mainly at the functional group, but some involve hydrogen atoms attached to the OH-bearing carbon atom or to an adjacent carbon atom. We saw earlier how methanol and ethanol are oxidized by liver enzymes to form aldehydes. This alcohol has the OH group on a carbon atom that is attached to two other carbon atoms, so it is a secondary alcohol; oxidation gives a ketone. (C). Can a tertiary alcohol undergo dehydration? Secondary alcohols are oxidized to ketones. [ "article:topic", "showtoc:no", "license:ccbyncsa" ], \(\mathrm{CH_3CHOHCH_3\underset{180^\circ C,\: excess\: acid}{\xrightarrow{conc\: H_2SO_4}} CH_3COCH_3+H_2O}\), \(\mathrm{2CH_3CHOHCH_3 \underset{180^\circ C,\: excess\: acid}{\xrightarrow{conc\: H_2SO_4}}(CH_3)_2CHOCH(CH_3)_2+H_2O}\). The oxidation of isopropyl alcohol by potassium dichromate (K2Cr2O7) gives acetone, the simplest ketone: Unlike aldehydes, ketones are relatively resistant to further oxidation, so no special precautions are required to isolate them as they form. Register now! Draw the structure of the alkene formed by the dehydration of cyclohexanol. Distinguish 1°, 2°, and 3° alcohols. This can be seen as a transesterification, acid and some other ester would be needed to form cyclohexylacetate; First, oxidize the alcohol to a ketone, take for example Dess-Martin Periodinane, then use an allyl grignard to form 1-allylcyclohexan-1-ol Of the three major kinds of alcohol reactions, which are summarized in Figure \(\PageIndex{1}\), two—dehydration and oxidation—are considered here. We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. Both dehydration and hydration reactions occur continuously in cellular metabolism, with enzymes serving as catalysts and at a temperature of about 37°C. Name each reactant and product. The third reaction type—esterification—is covered elsewhere. No reaction occurs. Alcohols can be dehydrated to form either alkenes (higher temperature, excess acid) or ethers (lower temperature, excess alcohol). In a reaction, compound W with the molecular formula C4H10O is converted to compound X with the formula C4H8O. This alcohol has the OH group on a carbon atom that is attached to three other carbon atoms, so it is a tertiary alcohol. The oxidation reactions we have described involve the formation of a carbon-to-oxygen double bond. 3. Tertiary alcohols are not readily oxidized. The overall type of reaction is the same as that in the conversion of isopropyl alcohol to acetone. Thus, the carbon atom bearing the OH group must be able to release one of its attached atoms to form the double bond. Is Y oxidized, reduced, or neither? The idea is that if you know the chemistry of a particular functional group, you know the chemistry of hundreds of different compounds. The first step is to recognize the class of each alcohol as primary, secondary, or tertiary. Describe the nucleophilic substitution reactions that can be used to prepare alcohols, ethers, thiols, and sulfides. Look at conjugated base stability. Solutions. ANSWERS 1) I 2) Br + CN CN + Br 3) H2O < CH3CO2-< HO-< CH3S- 4) H CN R 5) This is an Sn2 reaction. Show all organic products – if two or more products form, indicate These reactions can also be carried out in the laboratory with chemical oxidizing agents. organic chemistry i – practice exercise alkene reactions and mechanisms for questions 1-24, give the major organic product of the reaction, paying particular attention to regio- and stereochemical outcomes. Free LibreFest conference on November 4-6! Cl withdraws electron density. 4. This alcohol has the OH group on a carbon atom that is attached to only. Because a variety of oxidizing agents can bring about oxidation, we can indicate an oxidizing agent without specifying a particular one by writing an equation with the symbol [O] above the arrow. 3. The reaction removes the OH group from the alcohol carbon atom and a hydrogen atom from an adjacent carbon atom in the same molecule: Under the proper conditions, it is possible for the dehydration to occur between two alcohol molecules.
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