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Chapter 26: Q 27. (page 1070)

Draw the products (including stereoisomers) formed in each reaction.

Short Answer

Expert verified

Answer

Product of a

Product of b

d.Product of d

Step by step solution

01

Simmons-Smith reaction

The reaction involves the carbenoid formation that undergoes a cheletropic reaction, followed by the reaction with the C=C (alkene) to form a cyclopropane. This reaction is stereoselective.

02

Addition of dihalocarbenes to alkenes

The reaction takes place with syn-addition. The position of the substituted groups on alkene remains the same in cyclopropane.

03

Products of the given reaction

a. The stereoselective product is shown hereunder.

Product of a

b. The following reaction is the addition of dihalocarbenes to alkenes. The syn-addition product is shown hereunder.


c. The following reaction is the addition of dihalocarbenes to alkenes. The syn-addition product is shown hereunder.

Product of c

d. The following reaction is the addition of dihalocarbenes to alkenes. The syn-addition product is shown hereunder.

Product of d

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Most popular questions from this chapter

Draw the products formed in each reaction.

The reaction of cyclohexene with iodo-benzene under Heck conditions forms E, a coupling product with the new phenyl group on the allylic carbon, but none of the “expected” coupling product F with the phenyl group bonded directly to the carbon–carbon double bond.

a. Draw a stepwise mechanism that illustrates how E is formed.

b. Step [2] in Mechanism 26.2 proceeds with syn addition of Pd and R' to the double bond.What does the formation of E suggest about the stereochemistry of the elimination reaction depicted in Step [3] of Mechanism 26.2?

Draw the coupling product formed when each pair of compounds is treated with Pd(OAc)2, P(o-tolyl)3, and Et3N.

What product is formed by ring-closing metathesis of each compound?

a.

b.

Draw a stepwise mechanism for the following reaction.
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