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Chapter 22: 37P (page 868)

Devise a synthesis of each alcohol from organic alcohols having one or two carbons and any required reagents.

a.

b.

c.

d.

Short Answer

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Answer

The synthesis of each alcohol from organic alcohols having one or two carbons, and any required reagents are shown below:

Step by step solution

01

Step-by-Step Solution Step 1: Analysis of the retrosynthetic pathway

The retrosynthetic analysis obtains the required reagents and reactants.

The retrosynthetic approach of all the reactions are shown below

02

Final synthetic route

The final products are obtained by the stepwise methods using proper reagents and reactants.

By observing the retrosynthetic pathway, the synthesis of each alcohol from organic alcohols having one or two carbons, and any required reagents are shown below:

Product formation for c.

Product formation for d.

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Most popular questions from this chapter

stereochemistry of the products of reduction depends on the reagent used,as you learned in Sections 20.5 and 20.6. With this in mind, how would you convert3,3-dimethylbutan-2-one [CH3COC(CH3)3] to: (a) racemic 3,3-dimethylbutan-2-ol[CH3CH(OH)C (CH3)3] ;(b) only (R)-3,3-dimethylbutan-2-ol; (c) only (S)-3,3-dimethylbutan-2-ol?

Why can’t 1-methylcyclohexanol be prepared from a carbonyl compound by reduction?

Question: What products are formed when all of the amide and ester bonds are hydrolyzed in each of the following compounds? Tamiflu [part (a)] is the trade name of the antiviral agent oseltamivir, thought to be the most effective agent in treating influenza. Aspartame [part (b)] is the artificial sweetener used in Equal and many diet beverages. One of the products of this hydrolysis reaction is the amino acid phenylalanine. Infants afflicted with phenylketonuria cannot metabolize this amino acid, so it accumulates, causing mental retardation. When the affliction is identified early, a diet limiting the consumption of phenylalanine (and compounds like aspartame that are converted to it) can make a normal life possible

a.

b.

Question:(a) Propose an explanation for the difference in the frequency of the carbonyl absorptions of phenyl acetate (1765 cm-1 ) and cyclohexyl acetate (1738 cm-1).(b) Which carbonyl group is more effectively stabilized by resonance?(c) Which ester reacts faster when treated with aqueous base?

Draw the products of each reduction reaction.

a.

b.

c.

d.
See all solutions

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