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Chapter 14: 27Ea (page 447)

What product (s) would you expect to obtain from reaction of 1,3-cyclohexadiene with each of the following?

(a) 1 mol Br2inCH2Cl2

Short Answer

Expert verified

1,3 cyclohexadiene is a an unsaturated six member ring where two conjugated double bonds are present. When conventional alkenes undergo halogenation (chlorination and bromination), vicinal di halides (halogen atoms on adjacent carbon atoms) are obtained. But dienes react differently with halogens (Br2).Reaction of 1,3-cyclohexadiene with 1 mol of Br2inCH2Cl2gives to isomeric products (dibromo derivatives).

Reaction

Step by step solution

01

Reaction of 1,3-cyclohexadiene with 1 mol of Br2in CH2Cl2

1,3 cyclohexadiene is a an unsaturated six member ring where two conjugated double bonds are present. When conventional alkenes undergo halogenation (chlorination and bromination), vicinal di halides (halogen atoms on adjacent carbon atoms) are obtained. But dienes react differently with halogens (Br2).Reaction of 1,3-cyclohexadiene with 1 mol of Br2inCH2Cl2gives to isomeric products (dibromo derivatives).

Reaction

02

Explanation

The reason for the formation of two isomeric products is that, the carbocation formed during the reaction is resonance stablised, leading to the formtation of two products.

Reaction

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Most popular questions from this chapter

An extremely useful diene in the synthesis of many natural products is

known as Danishefsky’s diene. This compound is useful because after

the Diels–Alder reaction it can be converted into a product that could

not be accessed by a typical Diels–Alder reaction. Show the Diels–Alder

adduct and propose a mechanism that accounts for the final products.

How could you use Diels-Alder reactions to prepare the following products ? Show the starting diene and dienophile in each case.

a)

Question:βOcimene is a pleasant-smelling hydrocarbon found in the leaves of

certain herbs. It has the molecular formula and a UV absorption

maximum at 232 nm. On hydrogenation with a palladium catalyst,

2,6-dimethyloctane is obtained. Ozonolysis of βOcimene, followed by

treatment with zinc and acetic acid, produces the following four

fragments:

(a)How many double bonds does βocimene have?

(b)Is βocimene conjugated or non-conjugated?

(c)Propose a structure for βocimene.

(d)Write the reactions, showing starting material and products.

Show the product of the Diels–Alder reaction of the following dienewith 3-buten-2-one, H2C=CHCOCH3. Make sure you show the fullstereochemistry of the reaction product.

Ergosterol, a precursor of vitamin D, has λmax=282nm and molar absorptivity ε= 11900. What is the concentration of ergosterol in a solution whose absorbance A=0.065 with a sample pathlength l=1.0cm?
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