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Chapter 11: Q16P (page 559)

Explain the products observed in the following reaction of an alcohol with the Lucas reagent.

Short Answer

Expert verified

Lucas reagent differentiates the “primary, secondary and tertiary” alcohol present in any chemical sample.

Chemically Lucas reagent is the mixture of concentrated HCl andZnCl2.

Step by step solution

01

Step 1: Lucas Reagent

Lucas reagent differentiates the “primary, secondary and tertiary” alcohol present in any chemical sample.

Chemically Lucas reagent is the mixture of concentrated HCl andZnCl2.

02

Reaction of alcohol with the Lucas reagent

(1R,2R)-1,2-dimethyl cyclohexanol When reacted with Lucas reagent protonation of (1R,2R)-1,2-dimethyl cyclohexanol happen which convert hydroxy group to good leaving group water

Removal of water as an excellent leaving group leads to planar tertiary carbocation formation. The upcoming nucleophile (Cl- ) can approach from both top and bottom, giving cis (1R, 2R) 1-chloro-1,2-dimethylcyclohexane and trans (1S,1R)-1-chloro-1,2-dimethylcyclohexane isomers as products.

Reaction of alcohol with Lucas reagent

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Most popular questions from this chapter

Give the structure of the principal product(s) when each of the following alcohols reacts with (1) Na2Cr2O7/H2SO4 (2) PCC, (3) DMP, and (4) 1 equiv NaOCl-TEMPO.

(a)octan-1-ol (b)octan-3-ol

(c) 4-hydroxydecanal (d) 1-methylcyclohexan-1,4-diol

Predict the products of the reactions of the following compounds with:

(1) chromic acid or excess sodium hypochlorite with acetic acid.

(2)PCC or NaOCl (1 equivalent) with TEMPO.

(a)cyclohexanol (b)1-methylcyclohexanol

(c)cyclopentylmethanol (d)cyclohexanone

(e)cyclohexane (f)1-phenylpropan-1-ol

(g)hexan-1-ol (h)acetaldehyde, CH3CHO

The following reaction involves a starting material with a double bond and a hydroxyl group, yet its mechanism resembles a pinacol rearrangement. Propose a mechanism, and point out the part of your mechanism that resembles a pinacol rearrangement.

Two products are observed in the following reaction.

(a) Suggest a mechanism to explain how these two products are formed.

(b) Your mechanism for part (a) should be different from the usual mechanism of the reaction of SOCl2 with alcohols. Explain why the reaction follows a different mechanism in

this case.

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

(a)

(b)

(c)

(d)

See all solutions

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