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Aldol Condensation - Introduction to Organic Chemistry - Quiz - Document's extract

Exams, Organic Chemistry

Post: January 1st, 2013
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CHEM Part I. Multiple Choice- Circle the correct answer for each question below (30 points). 1. What is the product of this reaction?
O O 1. NaOEt 2. H3O+

OCH3

Li, tBuOH NH3

O

O

a.

O O

b.
O

a.

OCH3

b.
Li

H

O

c.
O O

OCH3

d.

OCH3

c.

O O

O

d.
O

7.
O O H

What type of reaction is shown below?
O Cl O H

2.

Which best represents a step in the mechanism for the aldol condensation?
a.
H3C O + H
+ H3C H H2C H H3C

O H2C
O

H
O H

H3C
O H

b.

O

c.
H3C

O + H2C

O H H3C

O

O H

d.

O + H3C H H2C H

O H H3C

8.

a. Oxidation b. Reduction c. Nucleophilic Aromatic Substitution d. Electrophilic Aromatic Substitution What is the product of this reaction?
O O CH3 1. NaOMe 2. HCl
O OCH3 O CH3 O

O

O H

H3CO
OH O

3.

Rank the following in increasing order of acidity (least to most).
O CO2H CHO CO2CH3

a.
O

b.

c.
I II III IV

O

d.

OCH3

4.

a. II, III, I, IV b. III, I, II, IV c. IV, I, III, II d. IV, III, I, II Which is the best way to accomplish this synthesis?
O O O O Ph

9.

Which group would undergo migration the fastest in the following reaction?
O R CF3CO3H O O R

a.

NaOEt

PhCH2Br

H3O+

a. R = Ph c. R = CH2CH3

b. R = t-butyl d. R = H

b.
c.

PhCH2MgBr
NaOH, H2O

H3O+
H3O
+

NaOH, H2O
PhCH2MgBr H3O
+

10.

What is the product of this reaction?
O CH3 NO2 Fe, HCl

d.

Ph3P=CHPh

H2, Pt

NaOH, H2O

H3O

+
O
O

5.

Which of the following is an example of a reduction reaction? a. Alkene to epoxide b. Alkane to alkyl halide c. Acid chloride to aldehyde d. Alkene to diol 6. What is the product of this reaction?

a.

H2N

b.

H2N

c.

H2N

d.

H2N

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Part II. 1. Rank the following in order of increasing acidity (least to most) (7 points):
H OHC H O OCH3 H H O H OH O H O

2.

Alkylation of unsymmetrical ketones is a very important reaction. One can easily predict the type of product formed by careful control of the reaction conditions. Using the following example, explain how you would obtain both products (your explanation should include the
reason why each product is formed) (10 points).
O CH3 1. LDA, THF 2. CH3I O CH3 CH3 O + H3C CH3

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3.

The following reaction is an example of a Stork Enamine reaction. When running the reaction on an unsymmetrical ketone only one product is formed. Predict the sole product for the following reaction and provide reasoning for this observation (6 points).
O + N H 1. HOAc ? 2. CH3I 3. HCl, H2O

4.

Predict the major products for the following reactions including relative stereochemistry where appropriate. If no reaction occurs, write NR (15 points).

O

a.

CH3 Br

NaOCH3 CH3OH, 25 °C

O

b.

1. CF3CO3H H 2. LAH

O

c.

NaOH, Br2 CH3 excess

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5.

Determine the major product for the following reactions. Include a complete reaction mechanism with all appropriate stereochemistry (12 points)
O O

a.
NaOH

b.

1. O3, -78 °C 2. H2O2

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6.

Show how you would synthesize the following compounds from the indicated starting materials (20 points).
O O OEt O

a.

EtO

O

b.

O

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Bonus 1. In chapter 19, we discussed a variety of condensation reactions (aldol, claisen, etc.). These reactions are powerful in that they form carbon-carbon bonds fairly easily. The Knoevenagel condensation is a related reaction to those other condensation reactions. The reaction involves the condensation of a β-dicarbonyl compound and an aldehyde. Predict the product of the following series of reactions where the second step is a Knoevenagel condensation (15 points).
O O + Ph OCH3 1. NaOCH3 2. benzaldehyde, H+

2.

The Mannich reaction is a reaction that substitutes the α-carbon of a ketone with an amine. Propose a mechanism for the following Mannich reaction (10 points)
O + H O H + H N HOAc O N

3.

Provide three different ways to carry out the following transformation (9 points).
O

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