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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

Compound A is an optically active alcohol. Treatment with chromic acid converts A into a ketone, B. In a separate reaction, A is treated with PBr3, converting A into compound C. Compound C is purified, and then it is allowed to react with magnesium in ether to give a Grignard reagent, D. Compound B is added to the resulting solution of the Grignard reagent. After hydrolysis of the initial product (E), this solution is found to contain 3,4 dimethylhexan-3-ol. Propose structures for compounds A, B, C, D, and E.

Use resonance forms of the conjugate bases to explain why methanesulfonic acid (CH3SO3H,pKa= -2.6) is a much stronger acid than acetic acid (CH3COOH,pKa =4.8)

Show the alcohol and the acid chloride that combine to make the following esters.

(a)

(b)

(c)

(d)

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?
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