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Chapter 11: Q20P (page 562)

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.

Short Answer

Expert verified

(a)

(b) Due to the formation of two stable allylic carbocations, the upcoming chloride nucleophile ion attacks result in the formation of two products.

Step by step solution

01

Step 1: Mechanism of forming two products for the given reaction

In the first step, nonbonding electrons of the hydroxy oxygen atom attack the electrophilic sulfur atom of thionyl chloride. A chloride ion is expelled, and a proton is lost to give a chlorosulfite ester.

In the next step, leaving group SOCl leaves forming the stable allylic carbocation (two possibilities of forming allylic carbocation )

In the last step, the nucleophile (Cl- ) delivered to both allylic carbocations formed, resulting in the formation of the two products.

Mechanism of forming the two products

02

 Mechanism different from the usual mechanism of the reaction of  with alcohol

In the given reaction, there is the possibility of forming two intermediate allylic carbocations, which arevery stable and thus it is very long-lived. Ion pair is escaped here and becomes free carbocation, and the nucleophile chloride attack on the two possible allylic carbocations formed to form two products.

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Most popular questions from this chapter

Both cis- and trans-2-methylcyclohexanol undergo dehydration in warm sulfuric acid to give 1-methylcyclohexene as the major alkene product. These alcohols can also be converted to alkenes by tosylation usingand pyridine, followed by elimination using KOC(CH3)3as a strong base. Under these basic conditions, the tosylate of cis-2-methylcyclohexanol eliminates to give mostly 1-methylcyclohexene, but the tosylate of trans-2-methylcyclohexanol eliminates to give only 3-methylcyclohexene. Explain how this stereochemical difference in reactants controls a regiochemical difference in the products of the basic elimination, but not in the acid-catalyzed elimination.

Give the structures of the products you would expect when each alcohol reacts with

(1) HCl, ZnCl2; (2) HBr; (3) PBr3; (4) P/I2; and (5) SOCl2.

(a) butan-1-ol (b) 2-methylbutan-2-ol

(c) 2,2-dimethylbutan-1-ol (d) cis-3-methylcyclopentanol

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

Neopentyl alcohol, (CH3)3CCH2OH, reacts with concentrated HBr to give 2-bromo-2-methylbutane, a rearranged product. Propose a mechanism for the formation of this product.

Compound A is an optically active alcohol. Treatment with chromic acid converts A into a ketone, B. In a separate reaction, A is treated with PBr3, converting A into compound C. Compound C is purified, and then it is allowed to react with magnesium in ether to give a Grignard reagent, D. Compound B is added to the resulting solution of the Grignard reagent. After hydrolysis of the initial product (E), this solution is found to contain 3,4 dimethylhexan-3-ol. Propose structures for compounds A, B, C, D, and E.
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