Both cis- and trans-2-methylcyclohexanol undergo dehydration in warm sulfuric acid to give 1-methylcyclohexene as the major alkene product. These alcohols can also be converted to
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- An unknown alcohol with a molecular formula of C7H14O was oxidized to an aldehyde with HOCl. When an acidic solution of the alcohol was distilled,two alkenes were obtained. The alkene formed in greater yield was determined to be 1-methylcyclohexene. The other alkene formed the original unknown alcohol when treated with BH3/THF followed by H2O2, HO-, and H2O. Identify the unknown alcohol.arrow_forwardCompound X has molecular formula C5H10. In the presence of a metal catalyst, compound X reacts with one equivalent of molecular hydrogen to yield 2-methylbutane. (1) Suggest three possible structures for compound X. (2) Hydroboration-oxidation of compound X yields a product with no chirality centers. Identify the structure of compound X.arrow_forwardWrite structural formulas for all ketones with the molecular formula C6H12O and give each its IUPAC name. Which of these ketones are chiral?arrow_forward
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- 1. Deduce the structure of each compound from the information given. All unknowns in this problem have molecular formula C8H12. (a) Upon catalytic hydrogenation, unknown W gives cyclooctane. Ozonolysis of W, followed by reduction with dimethylsulfide, gives octanedioic acid, HOOC—(CH2)6—COOH. Draw the structure of W. (b) Upon catalytic hydrogenation, unknown X gives cyclooctane. Ozonolysis of X, followed by reduction with dimethyl sulfide, gives two equivalents of butanedial, O=CH—CH2CH2—CH=O. Draw the structure of X.arrow_forwardCompound A and compound B are different alcohols with the same molecular formula of C4H10O. When reacted with chromic acid (H2CrO4), compound A and compound B produce compound C and compound D, respectively. Compound C has a molecular formula of C4H8O2. Compound E is obtained when compound A reacts with pyridinium chlorochromate (PCC) in a solvent such as dichloromethane (CH2Cl2). Draw the structure of compound A, B, C, D and E.arrow_forwardAn optically active monoterpene (compound A) with molecular formula C10H18O undergoes catalytic hydrogenation to form an optically inactive compound with molecular formula C10H20O (compound B). When compound B is heated with acid, followed by reaction with O3 and then with dimethyl sulfide, one of the products obtained is 4-methylcyclohexanone. Give possible structures for compounds A and B.arrow_forward