Chapter 10, Problem 10.60AP

Interpretation Introduction

(a)

Interpretation:

The step which is rate-limiting due to which the primary isotope effect is observed while the oxidation of deuterated isopropyl alcohol is to be stated.

Concept introduction:

Primary and secondary alcohols can be oxidized into aldehydes and ketones using Cr(VI) compounds as they are very good oxidizing agents. Few forms of chromium used to oxidize are chromate ${\text{CrO}}_{\text{4}}^{\text{2-}}$ and dichromate ${\text{Cr}}_2{\text{O}}_7^{\text{2-}}$ and chromium trioxide (${\text{CrO}}_3$). Primary alcohols are oxidized into aldehydes and secondary alcohols are oxidized into ketones.

Interpretation Introduction

(b)

Interpretation:

An explanation as to why the deuterated aldehyde is the major product when either (S) or (R)-1-deuterioethanol is oxidized with PCC in CH₂Cl₂ is to be stated.

Concept introduction:

Primary and secondary alcohols can be oxidized into aldehydes and ketones using Cr(VI) compounds as they are very good oxidizing agents. Few forms of chromium used to oxidize are chromate ${\text{CrO}}_{\text{4}}^{\text{2-}}$ and dichromate ${\text{Cr}}_2{\text{O}}_7^{\text{2-}}$ and chromium trioxide (${\text{CrO}}_3$). Primary alcohols are oxidized into aldehydes and secondary alcohols are oxidized into ketones.

Interpretation Introduction

(c)

Interpretation:

An explanation as to why no deuterated aldehyde product is obtained on oxidation of with alcohol dehydrogenase and NAD⁺ is to be stated.

Concept introduction:

The two hydrogens of ethanol are enantiotopic in nature. That is substitution of one hydrogen by another group will lead to R-isomer while for the other will lead to S-isomer. The alcohol dehydrogenase reaction of isotopically substituted ethanol can be carried out in order to distinguish them as the reaction is stereospecific in nature.