Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 22, Problem 22.55AP
Interpretation Introduction

(a)

Interpretation:

The principal organic product expected when 3-buten-2-one reacts with HBr is to be stated.

Concept introduction:

The α,β- unsaturated carbonyl compounds undergo a variety of addition reactions. The addition occurs either at the unsaturated part, at carbonyl group or at the position that involves both the parts. Such type of addition reaction of α,β- unsaturated carbonyl compounds that involves conjugated addition is known as Michael addition.

Expert Solution
Check Mark

Answer to Problem 22.55AP

The principal organic product obtained when 3-buten-2-one reacts with HBr is shown below.

Organic Chemistry, Chapter 22, Problem 22.55AP , additional homework tip  1

Explanation of Solution

The principal organic product obtained when 3-buten-2-one reacts with HBr is shown below.

Organic Chemistry, Chapter 22, Problem 22.55AP , additional homework tip  2

Figure 1

In this reaction, the addition of HBr occurs only on the carbon-carbon double bond. This reaction is a simple addition to the double bond. The addition product here does not follow the Markonikov’s rule. In the product, hydrogen will add to that carbon of the double bond that has the least number of hydrogens.

Conclusion

The principal organic product obtained when 3-buten-2-one reacts with HBr is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation:

The principal organic product expected when 3-buten-2-one reacts with H2,Pt(cat.) is to be stated.

Concept introduction:

The α,β- unsaturated carbonyl compounds undergo a variety of addition reactions. The addition occurs either at the unsaturated part, at carbonyl group or at the position that involves both the parts. Such type of addition reaction of α,β- unsaturated carbonyl compounds that involves conjugated addition is known as Michael addition.

Expert Solution
Check Mark

Answer to Problem 22.55AP

The principal organic product obtained when 3-buten-2-one reacts with H2,Pt(cat.) is shown below.

Organic Chemistry, Chapter 22, Problem 22.55AP , additional homework tip  3

Explanation of Solution

The principal organic product obtained when 3-buten-2-one reacts with H2,Pt(cat.) is shown below.

Organic Chemistry, Chapter 22, Problem 22.55AP , additional homework tip  4

Figure 2

In this reaction, the addition of H2 occurs only on the carbon-carbon double bond. This reaction is a simple addition to the double bond. This reaction is the selective reduction of the double bond in the presence of the carbonyl group.

Conclusion

The principal organic product obtained when 3-buten-2-one reacts with H2,Pt(cat.) is shown in Figure 2.

Interpretation Introduction

(c)

Interpretation:

The principal organic product expected when 3-buten-2-one reacts with LiAlH4, then H2O is to be stated.

Concept introduction:

The α,β- unsaturated carbonyl compounds undergo a variety of addition reactions. The addition occurs either at the unsaturated part, at carbonyl group or at the position that involves both the parts. Such type of addition reaction of α,β- unsaturated carbonyl compounds that involves conjugated addition is known as Michael addition.

Expert Solution
Check Mark

Answer to Problem 22.55AP

The principal organic product obtained when 3-buten-2-one reacts with LiAlH4, then H2O is shown below.

Organic Chemistry, Chapter 22, Problem 22.55AP , additional homework tip  5

Explanation of Solution

The principal organic product obtained when 3-buten-2-one reacts with LiAlH4, then H2O is shown below.

Organic Chemistry, Chapter 22, Problem 22.55AP , additional homework tip  6

Figure 3

In this reaction, the addition of H2 occurs only on the carbonyl group. This reaction is the selective reduction of the carbonyl group in the presence of the double bond. The reduction of carbonyl groups leads to the formation of a secondary alcohol.

Conclusion

The principal organic product obtained when 3-buten-2-one reacts with LiAlH4, then H2O is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation:

The principal organic product expected when 3-buten-2-one reacts with HCN in water, pH10 is to be stated.

Concept introduction:

The α,β- unsaturated carbonyl compounds undergo a variety of addition reactions. The addition occurs either at the unsaturated part, at carbonyl group or at the position that involves both the parts. Such type of addition reaction of α,β- unsaturated carbonyl compounds that involves conjugated addition is known as Michael addition.

Expert Solution
Check Mark

Answer to Problem 22.55AP

The principal organic product obtained when 3-buten-2-one reacts with HCN in water, pH10 is shown below.

Organic Chemistry, Chapter 22, Problem 22.55AP , additional homework tip  7

Explanation of Solution

The principal organic product obtained when 3-buten-2-one reacts with HCN in water, pH10 is shown below.

Organic Chemistry, Chapter 22, Problem 22.55AP , additional homework tip  8

Figure 4

In this reaction, the addition of HCN occurs only on the carbon-carbon double bond. The addition product here does not follow the Markonikov’s rule.

In the product, hydrogen will add to that carbon of the double bond that has the least number of hydrogens.

Conclusion

The principal organic product obtained when 3-buten-2-one reacts with HCN in water, pH10 is shown in Figure 4.

Interpretation Introduction

(e)

Interpretation:

The principal organic product expected when 3-buten-2-one reacts with Et2CuLi, then H3O+ is to be stated.

Concept introduction:

The α,β- unsaturated carbonyl compounds undergo a variety of addition reactions. The addition occurs either at the unsaturated part, at carbonyl group or at the position that involves both the parts. Such type of addition reaction of α,β- unsaturated carbonyl compounds that involves conjugated addition is known as Michael addition.

Expert Solution
Check Mark

Answer to Problem 22.55AP

The principal organic product obtained when 3-buten-2-one reacts with Et2CuLi, then H3O+ is shown below.

Organic Chemistry, Chapter 22, Problem 22.55AP , additional homework tip  9

Explanation of Solution

The principal organic product obtained when 3-buten-2-one reacts with Et2CuLi, then H3O+ is shown below.

Organic Chemistry, Chapter 22, Problem 22.55AP , additional homework tip  10

Figure 5

The reaction of α,β- unsaturated carbonyl compounds with R2CuLi leads to the conjugate addition of alkane molecule on the double bond. In the first step of the reaction, ethyl anion attack on the double-bonded carbons and leads to the formation of enolate ions. The enolate ion on acidic workup gives enol which on tautomerism gives ketone, hexan-2-one as a product.

Conclusion

The principal organic product obtained when 3-buten-2-one reacts with Et2CuLi, then H3O+ is shown in Figure 5.

Interpretation Introduction

(f)

Interpretation:

The principal organic product expected when 3-buten-2-one reacts with diethyl malonate and NaOEt, then H3O+ is to be stated.

Concept introduction:

The α,β- unsaturated carbonyl compounds undergo a variety of addition reactions. The addition occurs either at the unsaturated part, at carbonyl group or at the position that involves both the parts. Such type of addition reaction of α,β- unsaturated carbonyl compounds that involves conjugated addition is known as Michael addition.

Expert Solution
Check Mark

Answer to Problem 22.55AP

The principal organic product obtained when 3-buten-2-one reacts with diethyl malonate and NaOEt, then H3O+ is shown below.

Organic Chemistry, Chapter 22, Problem 22.55AP , additional homework tip  11

Explanation of Solution

The principal organic product obtained when 3-buten-2-one reacts with diethyl malonate and NaOEt, then H3O+ is shown below.

Organic Chemistry, Chapter 22, Problem 22.55AP , additional homework tip  12

Figure 6

The reaction of α,β- unsaturated carbonyl compounds with diethyl malonate leads to the conjugate addition of diethyl malonate molecule on the double bond. In the first step, acidic proton is abstracted by NaOEt from diethyl malonate. This then attacks in a conjugated manner at the double bond. The final product is obtained after the hydrolysis.

Conclusion

The principal organic product obtained when 3-buten-2-one reacts with diethyl malonate and NaOEt, then H3O+ is shown in Figure 6.

Interpretation Introduction

(g)

Interpretation:

The principal organic product expected when 3-buten-2-one reacts with ethylene glycol, HCl(cat.) is to be stated.

Concept introduction:

The α,β- unsaturated carbonyl compounds undergo a variety of addition reactions. The addition occurs either at the unsaturated part, at carbonyl group or at the position that involves both the parts. Such type of addition reaction of α,β- unsaturated carbonyl compounds that involves conjugated addition is known as Michael addition.

Expert Solution
Check Mark

Answer to Problem 22.55AP

The principal organic product obtained when 3-buten-2-one reacts with ethylene glycol, HCl(cat.) is shown below.

Organic Chemistry, Chapter 22, Problem 22.55AP , additional homework tip  13

Explanation of Solution

The principal organic product obtained when 3-buten-2-one reacts with ethylene glycol, HCl(cat.) is shown below.

Organic Chemistry, Chapter 22, Problem 22.55AP , additional homework tip  14

Figure 7

The reaction of 3-buten-2-one with ethylene glycol leads to the addition of ethylene glycol molecule on the carbonyl group. This reaction is the protection of the carbonyl group so that reaction can be done on the rest of the molecule. The end product of the reaction is a ketal.

Conclusion

The principal organic product obtained when 3-buten-2-one reacts with ethylene glycol, HCl(cat.) is shown in Figure 7.

Interpretation Introduction

(h)

Interpretation:

The principal organic product expected when 3-buten-2-one reacts with 1, 3-butadiene is to be stated.

Concept introduction:

Diels-Alder reaction is a cycloaddition reaction. The reaction is known as a [4+2] cycloaddition reaction in which a cis-diene and a dienophile react with each other in the presence of heat and a give a six-membered ring.

Expert Solution
Check Mark

Answer to Problem 22.55AP

The principal organic product obtained when 3-buten-2-one reacts with 1, 3-butadiene is shown below.

Organic Chemistry, Chapter 22, Problem 22.55AP , additional homework tip  15

Explanation of Solution

The principal organic product obtained when 3-buten-2-one reacts with 1, 3-butadiene is shown below.

Organic Chemistry, Chapter 22, Problem 22.55AP , additional homework tip  16

Figure 8

The reaction of 3-buten-2-one with 1, 3-butadiene is diels-alder reaction. The [4+2] cycloaddition of diene, 1, 3-butadiene and dienophile, 3-buten-2-one takes place. The double bond present in the 3-buten-2-one undergoes the addition reaction with 1, 3-butadiene to give six-membered ring product.

Conclusion

The principal organic product obtained when 3-buten-2-one reacts with 1, 3-butadiene is shown in Figure 8.

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Chapter 22 Solutions

Organic Chemistry

Ch. 22 - Prob. 22.11PCh. 22 - Prob. 22.12PCh. 22 - Prob. 22.13PCh. 22 - Prob. 22.14PCh. 22 - Prob. 22.15PCh. 22 - Prob. 22.16PCh. 22 - Prob. 22.17PCh. 22 - Prob. 22.18PCh. 22 - Prob. 22.19PCh. 22 - Prob. 22.20PCh. 22 - Prob. 22.21PCh. 22 - Prob. 22.22PCh. 22 - Prob. 22.23PCh. 22 - Prob. 22.24PCh. 22 - Prob. 22.25PCh. 22 - Prob. 22.26PCh. 22 - Prob. 22.27PCh. 22 - Prob. 22.28PCh. 22 - Prob. 22.29PCh. 22 - Prob. 22.30PCh. 22 - Prob. 22.31PCh. 22 - Prob. 22.32PCh. 22 - Prob. 22.33PCh. 22 - Prob. 22.34PCh. 22 - Prob. 22.35PCh. 22 - Prob. 22.36PCh. 22 - Prob. 22.37PCh. 22 - Prob. 22.38PCh. 22 - Prob. 22.39PCh. 22 - Prob. 22.40PCh. 22 - Prob. 22.41PCh. 22 - Prob. 22.42PCh. 22 - Prob. 22.43PCh. 22 - Prob. 22.44PCh. 22 - Prob. 22.45PCh. 22 - Prob. 22.46PCh. 22 - Prob. 22.47PCh. 22 - Prob. 22.48PCh. 22 - Prob. 22.49PCh. 22 - Prob. 22.50PCh. 22 - Prob. 22.51PCh. 22 - Prob. 22.52PCh. 22 - Prob. 22.53PCh. 22 - Prob. 22.54PCh. 22 - Prob. 22.55APCh. 22 - Prob. 22.56APCh. 22 - Prob. 22.57APCh. 22 - Prob. 22.58APCh. 22 - Prob. 22.59APCh. 22 - Prob. 22.60APCh. 22 - Prob. 22.61APCh. 22 - Prob. 22.62APCh. 22 - Prob. 22.63APCh. 22 - Prob. 22.64APCh. 22 - Prob. 22.65APCh. 22 - Prob. 22.66APCh. 22 - Prob. 22.67APCh. 22 - Prob. 22.68APCh. 22 - Prob. 22.69APCh. 22 - Prob. 22.70APCh. 22 - Prob. 22.71APCh. 22 - Prob. 22.72APCh. 22 - Prob. 22.73APCh. 22 - Prob. 22.74APCh. 22 - Prob. 22.75APCh. 22 - Prob. 22.76APCh. 22 - Prob. 22.77APCh. 22 - Prob. 22.78APCh. 22 - Prob. 22.79APCh. 22 - Prob. 22.80APCh. 22 - Prob. 22.81APCh. 22 - Prob. 22.82APCh. 22 - Prob. 22.83APCh. 22 - Prob. 22.84APCh. 22 - Prob. 22.85APCh. 22 - Prob. 22.86APCh. 22 - Prob. 22.87APCh. 22 - Prob. 22.88APCh. 22 - Prob. 22.89APCh. 22 - Prob. 22.90APCh. 22 - Prob. 22.91APCh. 22 - Prob. 22.92APCh. 22 - Prob. 22.93APCh. 22 - Prob. 22.94APCh. 22 - Prob. 22.95APCh. 22 - Prob. 22.96APCh. 22 - Prob. 22.97APCh. 22 - Prob. 22.98AP
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