BackPredict the products of the reactions of the following compounds with:
1. chromic acid or excess sodium hypochlorite with acetic acid.
2. PCC or NaOCl (1 equivalent) with TEMPO.
a. cyclohexanol
b. 1-methylcyclohexanol
c. cyclopentylmethanol
Predict the major products of the following reactions, including stereochemistry where appropriate.
(n) sodium ethoxide + 2-methyl-2-bromobutane
(o) octan-1-ol + DMSO + oxalyl chloride
(p) 4-cyclopentylhexan-1-ol + DMP reagent
Give the structure of the principal product(s) when each of the following alcohols reacts with (1) Na2Cr2O7/H2SO4, (2) PCC, (3) DMP, and (4) 1 equiv NaOCl-TEMPO.
a. octan-1-ol
b. octan-3-ol
Predict the products you expect when the following starting material undergoes oxidation with an excess of each of the reagents shown below.
a. chromic acid
b. PCC (pyridinium chlorochromate)
c. sodium hypochlorite/acetic acid
Predict the products formed by periodic acid cleavage of the following diols.
(a) CH3CH(OH)CH(OH)CH3
(b)
Predict the product of the oxidation reactions shown.
(a)
Every oxidation is accompanied by a reduction. Identify the species that is reduced in the Swern oxidation in Assessment 13.48.
Although trans-diols in rings cannot be cleaved using HIO₄ acyclic trans-diols can. Explain this discrepancy.
Predict the product of the following oxidation reactions.
(b)
δ-Hydroxyaldehydes are in equilibrium with their hemiacetal form. Predict the product that would form upon treatment of the hemiacetal with Dess–Martin periodinane.
Tertiary (3°)alcohols are not oxidized by chromic acid. Why?
Fill in the missing reactant, reagent, or product for each of the following oxidation reactions. react similarly to chromic acid
(d)
Predict the product of the following reactions.
(a)
Draw a mechanism for the following oxidation reactions.
(a)
Predict the product of the following oxidation reactions.
(a)