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Steps in the synthesis of compounds

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The professor wants us to do the following: Outline all steps in the possible synthesis of each of the following compounds from benzene and / or toluene, using any necessary aliphatic or inorganic reagents. Assume a pure para isomer that can be separated from an ortho/para mixture

a) ethylbenzene
b) phenyacetylene
c) isopropylbenzene
d) 2-phenylpropene
e) p-tertbutyltoluene
f) p-bromobenzylbromide
g) p-bromobenzoic acid
h) 1,2-diphenylethane
i) 1-phenylpropene (two ways)

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Solution Preview

For these questions, one must start with the basics of aromatic substitution reactions. For a) b) and c) starting with the appropriate reagents, a simple Friedel Crafts Alkylations should work just fine.

c) This can also be done by adding benzene and propene together in strong non-coordinating acids (H2SO4 or H3PO4).

d) The can be done by adding acetone to a grignard preparation of a benzene ring. (I am sure you can figure how to do this on your own), which will first result in ...

Solution Summary

This solution is provided in 339 words. It discusses Friedel Crafts Alkylations and what kinds of chemicals would react to give the final compound.

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Structural formulas, compounds, two-step synthesis

See the attached file for the full problems.

1. Write a structural formula for each of the following compounds:
a. 2,3-dimethyl-2-pentanol
b. 2-methyl-3-penten-1-ol
c. m-nitrophenol
d. potassium butoxide

2. Name each of the following compounds.

3. Arrange the following compounds in order of increasing acidity, and explain the reasons for your choice of order.
a. 2,4-dinitrophenol
b. phenol
c. 2,4-difluorocyclohexanol
d. cyclohexanol

4. Complete each of the following equations and name the products.

5. Show the structures of all possible acid-catalyzed dehydration products of the following. If more than one alkene is possible, predict which one will be formed in the largest amount.
a. 2-methyl-2-butanol
b. 1-methylcyclohexanol

6. Write an equation for each of the following reactions:
a. propanol + PBr3
b. 2-butanol + CrO3, H+
c. 2-methyl-1-pentanol + HCl
d. 1-butanol + SOCl2
e. 1-butanol + aqueous NaOH

7. Treatment of 3-hexene-2-ol with concentrated HCl gives a mixture of two products, 2-chloro-3-hexene and 4-chloro-2-hexene. Write a reaction mechanism that explains how both products are formed.

8. Write an equation for the two-step synthesis, 1-pentene to 2-pentanone.

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