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Organic Chemistry: Aldol Condensation and Reduction of Carbonyl

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ALDOL CONDENSATION: PREPARATION OF TRANS-p-ANISALACETOPHENONE
(Post Lab Questions: pp. 622-623, Problems 2, 5, 10)

2. Explain why the main reaction between acetophenone and p-anisaldehyde is the mixed-aldol reaction rather than (a) self-condensation of acetophenone or (b) the Cannizzaro reaction of p-anisaldehyde.

5. Propose a synthesis of cinnamaldehyde using a mixed-aldol condensation reaction.

10. Consider the spectral data for acetophenone.
a. In the functional group region of the IR spectrum, specify the absorptions associated with the carbonyl group and the aromatic ring.
b. In the 1H NMR spectrum, assign the various resonances to the hydrogen nuclei responsible for them.
c. For the 13C NMR data, assign the various resonances to the carbon nuclei responsible for them.

REDUCTION OF CARBONYL COMPOUNDS: PREPARATION OF FLUORENOL (Preparative)
(Post Lab Questions: pp. 584-585, Problems 2, 3, 6, 11)

2. After the reaction between sodium borohydride and the ketone is complete, the reaction mixture is treated with water and acid to produce the desired secondary alcohol. Explain this reaction by indicating the source of the hydrogen atom that ends up on the oxygen atom.
3. Sodium borohydride is fairly unreactive toward methanol, but adding a mineral acid to this solution results in the rapid destruction of the sodium borohydride. Explain.
6. Suggest a structure for the white precipitate formed in the reaction of 9-fluorenone with sodium borohydride.
11. A nitro group, a carbon-carbon double bond, a carbon-nitrogen double bond, and an aromatic ring may each be reduced under certain conditions. Rank these functional groups in order of increasing reactivity.

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The solution discusses aldol condensation and reduction carbonyl. Discussion for the post lab questions are included in the attached PDF file.

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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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