Predict the major product if the following reagents/reagents were used. Since this is a primary alcohol, there are some precautions necessary to avoid formation of the carboxyllic acid. (a) CrO3, H2SO4, H2O (b) Dess-Martin Periodinane (c) SOCl2 (d) NaH and 1-bromoethane (e) PBr3. Given that alcohols are relatively acidic and the protons transfer in solution, what would you expect to happen to the NMR spectrum if D2O was used as a solvent. –in phenols, —OH is connected to a benzene ring. Would the product be a racemic mixture or an enatiomerically pure product? No reaction is also a possible answer. OH a) H 2SO 4 heat OH CH 3-CH 2-CH-CH 2-CH 3 b) H 2SO 4 Stereochemistry 5. (Hint a rearrangement occurs). Assume no rearrangement for the first two product mechanisms. The following epoxide can be transformed into an alcohol using a grignard reagent, take for example allylmagnesium chloride. Organic Molecules and Chemical Bonding 2. Reactions, Mechanisms, Multiple Bonds 6. Given the following 1H NMR spectrum, draw the structure. Oxygen is more electronegative than carbon creating the polar bond. Name the compound, making sure to give the correct alkene geometry. Chapter 17: Alcohols and Phenols phenol (aromatic alcohol) pKa~ 10 alcohol pKa~ 16-18 O C H C O CC H enol keto chemistry dominated by the keto form CO H sp3 O H Alcohols contain an OH group connected to a saturated carbon (sp3) Phenols contain an OH group connected to a carbon of a benzene ring 77 O H H RO R' Starting with cyclohexanol, describe how you would prepare the following? Note how the carbocation after the rearrangement is resonance stabilized by the oxygen. Given the following alcohol, draw the structure from which it could be derived using only NaBH4. (a) 2 equivalents of RMgBr and H3O+ work-up (b) LiAlH4 and H3O+ work-up (c) NaBH4 and H3O+ work-up. Alkanes and Cycloalkanes 3. The integration values of each group of signals is given on the spectrum. Have questions or comments? NaBH4 is milder oxidant than LiAlH4. In the dehydration of this diol the resulting product is a ketone. This is also known as the Pinacol rearrangement. Normally: Oxidation is a loss of electrons; Reduction is a gain of electrons. Organic Chemistry by Robert C. Neuman, Jr. One common example of these are sugars, is the given the following sugar, allitol, also chiral? (a) (b) (c) No reaction. Chlorine, bromine, and iodine are common leaving groups used in organic chemistry. They can be prepared from many different types of compounds, and they can be converted into many different types of compounds. Draw the alcohol that the following ketones/aldehydes would have resulted from if oxidized. Note, NaBH4 is only a strong enough reducing agent to reduce ketones and aldehydes. Solutions. 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 Draw the product of the treatment of this epoxide with this grignard after being worked up with H2O. (sulfur is in the same column as oxygen)! Given the following 1H NMR spectrum, draw the structure. No reaction is also a possible answer. (a) (b) Indicate stereochemistry (c) (d), Draw and name all the alcohol isomers of C3H9O. Missed the LibreFest? What combination of carbonyl compound and grignard (use MgBr) reagent would yield the following alcohols (after workup)? In cyclohexanone, a ketone, indicate the polarity of the bond between oxygen and carbon. This compound actually has a plane of symmetry, the plane parallel to the carbon chain/backbone. –in alcohols, a hydroxyl group is connected to a carbon atom. Milder oxidants such as the Dess-Martin periodinane, and also PCC (there is no water to form the carboxyllic acid) would work. From mass spectroscopy analysis it was determined that a compound has the general formula C3H8O. Ch11 Reacns of Alcohols (landscape).docx Page 1 Reactions of Alcohols Alcohols are versatile organic compounds since they undergo a wide variety of transformations – the majority of which are either oxidation or reduction type reactions. Name each reactant and product. Haloalkanes, Alcohols, Ethers, and Amines 4. The more substituted alkene is favored, as more substituted alkenes are relatively lower in energy. Fill in the blanks of the following reaction scheme. We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. ORGANIC CHEMISTRY-II BCHCH-202 UTTARAKHAND OPEN UNIVERSITY Page 3 In some alcohols, the —OH group is attached to a sp 3 hybridised carbon next to the carbon-carbon double bond that is to an allylic carbon are known as allylic alcohols.


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