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Chapter 11: Q8P (page 551)

Unlike ethylene glycol, propylene glycol (propane-1, 2-diol) is non toxic because it oxidizes to a common metabolic intermediate. Give the structures of the biological oxidation products of propylene glycol.

Short Answer

Expert verified

Propylene glycol come under the category of diols comprising the IUPAC name, propane-1,2-diol. It is miscible with several solvents like water and chloroform.Glycols comprise low volatility and are non-irritating.

Step by step solution

01

Propylene glycol

Propylene glycol come under the category of diols comprising the IUPAC name, propane-1,2-diol. It is miscible with several solvents like water and chloroform.Glycols comprise low volatility and are non-irritating.

02

Biological oxidation of alcohols

The liver creates an enzyme, alcohol dehydrogenase (ADH) to remove ethanol. The removal of hydrogen atom from the alcohol happens with the help of the enzyme ADH. Nicotinamide adenine dinucleotide (NAD)serves as the oxidizing agent in this particular reaction.

03

Structures of the biological oxidation products of glycol

Propylene glycol also known as propan-1, 2-diol is nontoxic as it oxidizes to a common metabolic intermediate.

The structures of the biological oxidation products of propylene glycol can be given as:

The biological oxidation products of propylene glycol

The products formed due to the oxidation of propan-1, 2-diol are pyruvaldehyde, pyruvic acid and water.

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Most popular questions from this chapter

We have covered several oxidants that use a multi-valent atom (Cr, Cl, S, or I) as their active species, going from a higher oxidation state before the oxidation to a lower oxidation state after oxidizing the alcohol. Draw the structure of the following atoms, before and after the oxidation of an alcohol to a ketone or aldehyde. How many bonds to oxygen does each atom have before and after the oxidation?

(a) the Cr in chromic acid

(b) the Cl in sodium hypochlorite

(c) the S in the Swern oxidation

(d) the I in the DMP reagent

(e)the carbinol C in the alcohol that is oxidized.

Predict the products of the following reactions.

(a) cyclohexylmethanol + TsCl / pyridine (b) product of (a) + LiAlH4

(c) 1- methylcyclohexanol + H2SO4, heat (d) product of (c) + H2, Pt

When 1-cyclohexylethanol is treated with concentrated aqueous, the major product is 1-bromo-1-ethylcyclohexane.

(a)Propose a mechanism for this reaction.

(b) How would you convert 1-cyclohexylethanol to (1-bromoethyl)cyclohexane in good yield?

A student wanted to use the Williamson ether synthesis to make (R)-2-ethoxybutane. He remembered that the Williamson synthesis involves an SN2 displacement, which takes place with inversion of configuration. He ordered a bottle of (S)-butan-2-ol for his chiral starting material. He also remembered that the SN2goes best on primary halides and tosylates, so he made ethyl tosylate and sodium (S)-but-2-oxide. After warming these reagents together, he obtained an excellent yield of 2-ethoxybutane.

(a) What enantiomer of 2-ethoxybutane did he obtain? Explain how this enantiomer results from the SN2 reaction of ethyl tosylate with sodium (S)-but-2-oxide.

(b) What would have been the best synthesis of (R)-2-ethoxybutane?

(c) How can this student convert the rest of his bottle of (S)-butan-2-ol to (R)-2-ethoxybutane?

Predict the major products (including stereochemistry) when trans-3-methylcyclohexanol reacts with thefollowingreagents.

(a) PBr3

(b) SOCl2

(c) Lucas reagent

(d) concentrated HBr

(e) TsCl/pyridine, then NaBr
See all solutions

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