Predict the major products of the following reactions, including stereochemistry where appropriate.(a) (R)@butan@2@ol + TsCl in pyridine (b) (S)-2-butyl tosylate + NaBr(c) cyclooctanol + NaOCl>HOAc (d) cyclopentylmethanol + CrO3 # pyridine # HCl(e) cyclopentylmethanol + Na2Cr2O7>H2SO4 (f) cyclopentanol + HCl>ZnCl2(g) n@butanol + HBr (h) cyclooctylmethanol + CH3CH2MgBr(i) potassium tert@butoxide + methyl iodide (j) sodium methoxide + tert@butyl iodide(k) cyclopentanol + H2SO4>heat (l) product from (k) + OsO4>H2O2, then HIO4(m) sodium ethoxide + 1@bromobutane (n) sodium ethoxide + 2@methyl@2@bromobutane(o) octan-1-ol + DMSO + oxalyl chloride (p) 4-cyclopentylhexan-1-ol + DMP reagent
Predict the major products of the following reactions, including stereochemistry where appropriate.
(a) (R)@butan@2@ol + TsCl in pyridine (b) (S)-2-butyl tosylate + NaBr
(c) cyclooctanol + NaOCl>HOAc (d) cyclopentylmethanol + CrO3 # pyridine # HCl
(e) cyclopentylmethanol + Na2Cr2O7>H2SO4 (f) cyclopentanol + HCl>ZnCl2
(g) n@butanol + HBr (h) cyclooctylmethanol + CH3CH2MgBr
(i) potassium tert@butoxide + methyl iodide (j) sodium methoxide + tert@butyl iodide
(k) cyclopentanol + H2SO4>heat (l) product from (k) + OsO4>H2O2, then HIO4
(m) sodium ethoxide + 1@bromobutane (n) sodium ethoxide + 2@methyl@2@bromobutane
(o) octan-1-ol + DMSO + oxalyl chloride (p) 4-cyclopentylhexan-1-ol + DMP reagent
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