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Chapter 8: Q90P (page 379)

a. How could each of the following compounds be prepared from a hydrocarbon in a single step?

b. What other organic compound would be obtained from each synthesis?

Short Answer

Expert verified

Each of the following compounds be prepared from a hydrocarbon in a single step.

a) Cyclohexa-1,3-diene reacts with bromine molecule in the presence of water to get 4-bromocyclohex-2-en-1-ol.


Step by step solution

01

Step1:

Each of the following compounds be prepared from a hydrocarbon in a single step.

a) Cyclohexa-1,3-diene reacts with bromine molecule in the presence of water to get 4-bromocyclohex-2-en-1-ol.


02

Step 2:

a) 2-methylcyclohexa-1,3-diene reacts with bromine molecule to get 3-bromo-3-methylcyclohexa-1-ene.

b) 3-methylenecyclohex-1-ene reacts with hydrogen bromide to form 3-bromo-3-methylcyclohex-1-ene.


03

Step 3:

a)1-5, dimethylcyclohexa-1,3-diene reacts with water in the presence of sulphuric acid to form 3,5-dimethylcyclohex-2-en-1-ol.

b) 2,6-dimethylcyclohexa-1,3-diene reacts with water in the presence of sulphuric acid to get 3,5-dimethylcyclohex-2-en-1-ol.


04

Step 4

other organic compound would be obtained from each synthesis are as follows

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Most popular questions from this chapter

a. Draw resonance contributors for the following species, showing all the lone pairs:

1.CH2N2 2. N2O 3. NO2-

b. For each species, indicate the most stable resonance contributor.

Identify the kinetic and thermodynamic products of the following reaction:

Draw the resonance contributors for the following carbocation

Which compound in each set is aromatic? Explain your choice.

The heat of hydrogenation of 2,3-pentadiene, a cumulated diene, is 70.5 kcal/mol. What are the relative stabilities of cumulated, conjugated, and isolated dienes?
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