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

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

Short Answer

Expert verified

The reagent is the substance added to the organic compound called substrate, which gets changed by adding the particular reagent; as a result, a new organic compound as a product is formed.

Reagents are of the following types:

  • Free radical reagent
  • Electrophilic reagent

Nucleophilic reagent

Step by step solution

01

Reagent

The reagent is the substance added to the organic compound called substrate, which gets changed by adding the particular reagent; as a result, a new organic compound as a product is formed.

Reagents are of the following types:

  • Free radical reagent
  • Electrophilic reagent

Nucleophilic reagent

02

Predicting product of given reactant with the help of given reagent:

  1. Cyclohexyl methanol when reacted with tosyl chloride (TsCl) and pyridine from the product tosylate ester.

    Formation of tosylate ester
  2. Tosylate ester (product of (a) reaction) When reacted with lithium aluminum hydride (LiAIH4), forms toluene as a product.

    Formation of toluene
  3. 1- methyl cyclohexanol, when reacted with sulphuric acid in the presence of heat, has been reduced to the alkene; the mixture of an alkene-formed: major product is 1-methylcyclohex -1- ene, and the minor product is methylcyclohexane.

    Formation of 1-methylcyclohex -1- ene and methylcyclohexane
  4. 1-methylcyclohex -1- ene ( major product of (c) reaction ) When reduced with the help of H2/Pt form alkane toluene as a product.

    Formation of toluene

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.

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 a mechanism for each reaction.

(a)

(b)

Predict the products you expect when the following starting material undergoes oxidation with an excess of each of the reagents shown below.

(a)chromic acid

(b)PCC(pyridinium chlorochromate)

(c)sodium hypochlorite/ acetic acid

(d)DMSO and oxalyl chloride

(e)DMP(periodinane)reagent

Alcohols combine with ketones and aldehydes to form interesting derivatives, which we will discuss in Chapter 18. The following reactions show the hydrolysis of two such derivatives. Propose mechanisms for these reactions.

(a)

(b)

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.

Some alcohols undergo rearrangement or other unwanted side reactions when they dehydrate in acid. Alcohols may be dehydrated under mildly basic conditions using phosphorus oxy-chloride (POCl3) in pyridine. The alcohol reacts with phosphorus oxychlorides much like it reacts with tosyl chloride (Section 11-5), displacing a chloride ion from phosphorus to give an alkyl dichlorophosphate ester. The dichlorophosphate group is an outstanding leaving group. Pyridine reacts as a base with the dichlorophosphate ester to give an E2 elimination. Propose a mechanism for the dehydration of cyclohexanol by POCl3 in pyridine.

See all solutions

Recommended explanations on Chemistry Textbooks

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