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Structural formulas, compounds, two-step synthesis

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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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Solutions
1. A)

B)

C)

D)

2. A) p-nitrophenol
B) 2-methoxy-3-cyclopenten-1-ol
C)Sodium methoxide
D) 3-methyl-1,2-butanediol

3. The order should be d<c<b<a. Acidities are dependent on stability of the conjugate base. So draw the ...

Solution Summary

Structural formulas, compounds and two-step synthesis is examined.

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Organic Compounds, Synthesis of 2-hexanone, Grignard reagent, Aldol condensation reaction ...

Please see the attached file for the full problems.

1. Name each of the following compounds.

2. Write a structural formula for each of the following compounds.

a. benzyl methyl ketone
b. 2-pentenal
c. 2-chloro-3-hexanone
d. 2,3-dimethylpentanal

3. Write an equation for the synthesis of 2-hexanone by
a. oxidation of an alcohol
b. hydration of an alkyne

4. Write an equation for the reaction of propanal with each of the following reagents, and name the organic product.
a. cyanide ion
b. sodium borohydride
c. phenylmagnesium bromide, then H3O+

5. Using a Grignard reagent and the appropriate aldehyde or ketone, show how each of the following can be prepared.
a. 2-phenyl-2-butanol
b. 2-hexanol
c. 1-pentene-3-ol

6. Complete the equation for the reaction of

7. Give the structure of each product.

8. Write out the steps for the aldol condensation reaction between the enolate anion of propanal with pentanal.

9. Using Figure 16.1 on page 462 of your textbook, draw the Fisher projection formulas for the following:
a. L-ribose
b. L-arabinose
c. L-glucose
d. L-talose

10. Using Figure 16.1 on page 462 of your textbook, draw the Fisher projection formulas for the following and then convert them to three-dimensional representations.
a. L-threose
b. L-erythrose

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