Draw the products formed in each reaction.

a.

b.

c.

d.

e.

f.

g.

h.

Short Answer

Expert verified

Answer

a.

b.

c.

d.

e.

f.

g.

h.

Step by step solution

01

Coupling reactions

The coupling of an organic halide with an organometallic reagent or alkene results in new carbon-carbon (C-C) bond formation.

02

Types of coupling reactions

Numerous coupling reactions are present, and the important ones are mentioned below

  • The reaction of organic halide with organocuprate reagent
  • Suzuki reaction
  • Heck reaction
03

Predicting the product formed in the reaction

a.The reaction of chlorocyclohexene with the given organocuprate reagent results in the formation of 1-propylcyclohex-1-ene. The reaction can be given as:

Product formed from compound a

b.This reaction is a Suzuki reaction and is carried in the presence of a base. The reaction product is 3-m-tolylpyridine and the reaction can be given as:


Product formed from compound b

c.The given reaction is a Heck reaction. A substituted alkene is formed as the product in this reaction. The reaction product is 3-2-(furan-2-yl)vinyl)pyridine and the reaction can be given as:

Product formed from compound c

d.This reaction involves organocuprate reagents. The product formed in the reaction contains new C-C bonds. The product is (E)-undec-2-ene and the reaction can be given as:

Produ

Product formed from compound d

e.This is a Suzuki reaction and is carried out in the presence of a base. The product of the reaction is (2E, 4E)-hexa-2,4-diene. The reaction can be given as:

Product formed from compound e

f. This is a heck reaction and involves the formation of a substituted alkene. The reaction product is (Z)-methyl-3-(4-methoxyphenyl)acrylate. The reaction can be given as:

Product formed from compound f

g. This reaction is a Suzuki reaction and the alkyl halide is reacted with the organoborane to form the product. The reaction product is (E)-prop-1-enylbenzene and the reaction can be given as:

Product formed from compound g

h. The reaction is a Suzuki reaction. The organoborane reacts with the alkyl halide to form hex-1-enylbenzene and the reaction can be given as:

Product formed from compound h

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Most popular questions from this chapter

Draw the product formed from the ring-closing metathesis of each compound. Then, devisea synthesis of each metathesis starting material using any of the following compounds: CH2(CO2Et)2, alcohols with less than five carbons, and any needed organic and inorganicreagents.

a.

b.

Many variations of ring-closing metathesis have now been reported. Tandem ring-opening– ring-closing metathesis can occur with cyclic alkenes that contain two additional carbon– carbon double bonds. In this reaction, the cycloalkene is cleaved, and two new rings are formed. [1] What compounds are formed in this tandem reaction with the following substrates? [2] Devise a synthesis of the substrate in part (b) that uses a Diels–Alder reaction with diethyl maleate as the dienophile.

a.

b.

What steps are needed to convert but-1-ene CH3CH2CH=CH2 to octane role="math" localid="1649049664153" [CH3CH26CH3]using a coupling reaction with an organocuprate reagent? All carbon atoms in octane must come from but-1-ene.

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?

Devise a synthesis of each of the following compounds. Besides inorganic reagents, you may use hydrocarbons and halides having C’s, and CH2CHCOOCH3as starting materials. Each synthesis must use at least one of the carbon–carbon bond-forming reactions in this chapter.


b.

c.

d.

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