Logout Open In App
Open In App
Warning: foreach() argument must be of type array|object, bool given in /var/www/html/web/app/themes/studypress-core-theme/template-parts/header/mobile-offcanvas.php on line 20

Chapter 18: Q65E (page 594)

How would you prepare o-Hydroxyphenylacetaldehyde from phenol? More than one step is required.

o-Hydroxyphenylacetaldehyde

Short Answer

Expert verified

The answer is

Step by step solution

01

o-Hydroxyphenylaldehyde

The o-Hydroxyphenylacetaldehyde is an aromatic compound containing alcohol and an aldehyde functional group. It can undergo nucleophilic substitution reactions.

02

Explanation

The reaction for the synthesis of o-Hydroxyphenylacetaldehyde from phenol is shown below.

The hydroxyl group in phenol is protected using beta-methoxy ethoxy methyl ether (MEM). It is then treated with an ethane dial to give the substituted product. The product obtained then undergoes a reaction with tosyl hydroxide (TsOH) and Lithium aluminum hydride (LAH) to give the reduced product. It is then treated with acid to remove the protection of the hydroxyl group.

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Start your free trial

Over 30 million students worldwide already upgrade their learning with Vaia!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

Propose structures for compounds that have the following 1H NMR spectra:

(a) \({C_5}{H_{12}}S\) (An โ€“SH proton absorbs near 1.6 \(\delta \) )

(b) \({C_9}{H_{11}}BrO\)

(c) \({C_5}{H_{12}}{O_2}\)

The Zeisel method is an old analytical procedure for determining the number of methoxyl groups in a compound. A weighed amount of the compound is heated with concentrated HI, ether cleavage occurs, and the iodomethane product is distilled off and passed into an alcohol solution ofAgNO3 , where it reacts to form a precipitate of silver iodide. The AgI is then collected and weighed, and the percentage of methoxyl groups in the sample is thereby determined. For example, 1.06 g of vanillin, the material responsible for the characteristic odour of vanilla, yields 1.60 g of AgI. If vanillin has a molecular weight of 152, how many methoxyl groups does it contain?

When 2-methyl-2,5-pentanediol is treated with sulfuric acid, dehydration occurs and 2,2 dimethyltetrahydrofuran is formed. Suggest amechanism for this reaction. Which of the two oxygen atoms is mostlikely to be eliminated, and why?

Aldehydes and ketones undergo acid-catalyzed reaction with alcoholsto yield hemiacetals,compounds that have one alcohol-like oxygenand one ether-like oxygen bonded to the same carbon. Further reactionof a hemiacetal with alcohol then yields an acetal,a compound that hastwo ether-like oxygens bonded to the same carbon.

(a)Show the structures of the hemiacetal and acetal you would obtainby reaction of cyclohexanone with ethanol.

(b)Propose a mechanism for the conversion of a hemiacetal into anacetal.

Propose structures for compounds that have the following 1H NMR spectra:

(a) C5H12S (An โ€“SH proton absorbs near 1.6ฮด)

(b)C9H11BRO

(c)C5H12O2
See all solutions

Recommended explanations on Chemistry Textbooks

Inorganic Chemistry

Read Explanation

Physical Chemistry

Read Explanation

The Earths Atmosphere

Read Explanation

Kinetics

Read Explanation

Making Measurements

Read Explanation

Chemistry Branches

Read Explanation
View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.

Sign-up for free