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Chapter 11: A49P (page 588)

Predict the major products (including stereochemistry) when trans-3-methylcyclohexanol reacts with thefollowingreagents.

(a) PBr3

(b) SOCl2

(c) Lucas reagent

(d) concentrated HBr

(e) TsCl/pyridine, then NaBr

Short Answer

Expert verified

a.

b.

c.

d.

e.

Step by step solution

01

a. Reagent and Reaction

Phosphorous tribromide (PBr3 ) used in a reaction to convert alcohols to bromides. These reagent is used when the alcohol is primary/secondary.

When trans-3-methylcyclohexanol reacts with phosphorous tribromide forms 3-methyl-1-bromocyclohexane.

02

b. Reagent and Reaction

b. Thionyl chloride (SOCl2) used as chlorinating reagent to form aryl/alkyl chloride. When trans-3-methylcyclohexanol reacts with thionyl chloride to form 3-methyl-1-chlorocyclohexane.

03

c. Lucas Reagent and Reaction

Lucas reagent is used to differentiate/classify different types of alcohols (primary, secondary, tertiary).

When trans-3-methylcyclohexanol reacts with Lucas reagent form cis and trans-3-methyl-1-chlorocyclohexane.

04

d. Reagent and Reaction

HBr used in these reaction to form halo cyclohexane. It undergoes nucleophilic substitution reaction.

When trans-3-methylcyclohexanol reacts with concentrated form cis and trans-3-methyl-1-bromocyclohexane.

05

e. Reagent and Reaction

TsCl Used in these reaction as an activating group and pyridine neutralizes that generated by the reaction. Trans-3-methylcyclohexanol reacted with is reagent to form major product.

When trans-3-methylcyclohexanol reacted with and then with form 3-methyl-1-bromocyclohexane.

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Most popular questions from this chapter

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.

Under normal circumstances, tertiary alcohols are not oxidized. However, when the tertiary alcohol is allylic, it can undergo a migration of the double bond (called an allylic shift) and subsequent oxidation of the alcohol. A particularly effective reagent for this reaction is Bobbitt鈥檚 reagent, similar to TEMPO used in many oxidations. (M. Shibuya et al., J. Org. Chem., 2008, 73, 4750.)

Show the expected product when each of these 3掳 allylic alcohols is oxidized by Bobbitt鈥檚 reagent.

(a)

(b)

(c)

(d)

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)

The compound shown below has three different types of OH groups, all with different acidities. Show the structure produced after this compound is treated with different amounts of NaH followed by a methylating reagent. Add a brief explanation.

(a)1 equivalent of NaH, followed by 1 equivalent of CH3l and heat

(b)2 equivalents of NaH, followed by 2 equivalents of CH3l and heat

(c) 3 equivalents of NaH, followed by 3 equivalents of CH3l and heat

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
See all solutions

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