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Organic Structures: Reactions and Nomenclature

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Write the structural formula for the compounds cited below. Be sure to include all carbon and hydrogen!

(a) Ethylpropyl ether (b) 2 ethyl 2,4,4-trimethylpentanoic acid (c) methyl pentanoate

(d) hexachlorobenzene (e) 2,4,6-trichloro-3,5-dimethylphenol (f) Propylamine

Esterification is the reaction of a carboxylic acid and alcohol in the presence of an acid catalyst to produce an ester. Volatile esters often have a pleasant smell and are found in perfumes, essential oils, and pheromones, and give many fruits their scent.

(a) Draw the alcohol and the carboxylic acid from which the following ester can be made:

(b) Give the IUPAC name for the alcohol used in part (6a). __________________________

(c) Give the IUPAC name for the carboxylic acid used in part (6a). ___________________

(d) Draw the ester that is formed from the following reaction:

Give the IUPAC name for the ester formed in part (6d). ___________________________

Which of the reactants used in part (6d) has the higher boiling point, the alcohol or the carboxylic acid?

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The solution examines organic structures, reactions and nomenclature.

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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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