Question

Due 462 CHAPTER 1O Stracture and Symthesis of Alcohols mercaptan (thiol) The sulfur analogse of an alcobol, R-SH. (p 455) futually sobuble in any proportions. (p 432 An organiietallic peapont of the form R-Li. Ip.44n organometallic reagents) Compounds containing metal atoms carbon. (p. 440) organolithium reagent Raney nickel with a hydeosyl group bonded directly to an aromatic ring. up. 426) A finely divided nickel/aluminum alloy that has been treated with N a0H to dissoive out 451ed as a catalyst for the hydrogenaticn of ketones and aldehydes to alcohols. (p. Propan-2-ol. isopropyl alcohol. (p. 434) (noun) A plantigrade omnivorous quadruped that prevent from scoring in a game or contest (p. 453) rubbing alcohol thiols: (verb) o effectively synthesines sulfonie acid io tn aidic compound of formula R-SO,H, formed by vigoross oxidation of a t thiol thiolate lon wood alcohol (p. 460) (mercaptan) The sulfur [mercaptide) The R-Si analogue of an alcobol, R-SH.(p. 458) anion, formed by deprotonation of a thiol.(p 459) Methanol, methyl alcobol. (p. 433) STUDY PROBLEMS brormobenzene and any other reagents and solvents you neod, show how you would syntbesize the following compounds. Amy of these products (a) I-phenylpropan-1-o (d) 3-phenylprop-2-en-1-ol may be used as starting materials in subsequent parts of this problem. (b) 1-phemy propene (e) 2-phenylbutan-2-ol (c) 1-phenylpropan-2-ol 2-pheny lbut-2-ene 10-3リ Give a systematic (IUPAC) name for each alcohol. Classify each as primary, secondary, or tertiary Br- CHCH fe) CH2OH (el (0 10-32 Give systematic (aUPAC) names for the following diols and phenols OH OH OH CI Br Draw the structures of the following compounds (Inclades both new and old nanes.) (a) triphenylmethanol (d) 3-cyclopentylhexan-3-o (e) 2-cyclohexen-I-ol (b) 4 chlorornethyl heptan-3-1 (e) meso-2,4 pentanediol (h) (2R.3R)-2.3-hexanedio (k) 3-methylhex-4-yn-2-ol ( D cyelopentene glycol i) cyclopent-3-ene-1-thiol ) 3-tiodomethyl )phenol j) dimethyl disultide Predict which member of each pair has the higher boiling point, and explain the reasons for your predictions. (a) hexan-1-ol or 3.3-dimethylbutan-I-o (c) hexan-2-ol or hexane-1,5-diol (b) hexan-2-one or hexan-2-o (d) pentan-2-ol or hexan-2-o 10-35 Predict which member of each pair is more acidic, and explain the reasons for your predictions. (a) cyclopentanol or 3-chlorophenol (c) cyclohexanol or cyclohexanccarboxylic acid (b) cyclohexanol or cyclohexanethiol (d) butan-l-ol or 2.2-dichlorobutan-1-ol

Answer 1

10-31 он он 5-methyl-4-propylheptan-2.ol (Secondary) 4-(1-bromoethyl)heptan-3-ol 6-chloro.3-phenyloctan-3-ol (Secondary) (tertiary) он он он CH2OH cyclopent 1 en-1 ylmethanol (primary) .bromocyclohex.3 en-1 ol (1R,4S)-4-chlorocyclohex 2 en-1-ol (E)-4,5-dimethylhex-3-en-1-ol (Secondary,) (Secondary) (primary) 10-32 a) OH он b) 0 chloro 1 phenylhexane-1,5 diol1S,2S)-cyclohexane 1,2 diol c OH d) OH NO2 3-nitrophendol 4-bromo-2-chlorophenol 10-33 triphenylmethanol 4 (chloromethyl)heptan 3-ol 2-cyclohexen 1-ol CI он он meso-2,4-pentanediol cyclopentene glycol 3-cyclopentylhexan-3-ol он OH OH он 3-(iodomethyl)phenol (2R,3R)-2,3-hexanediol cyclopent-3 ene 1-thiol он SH но dimethyl disulfide 3-methylhex 4.yn-2-ol