Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Textbook Question
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Chapter 24, Problem 24.48P

Draw the organic products formed when butanal ( CH 3 CH 2 CH 2 CHO ) is treated with each reagent.

a. OH, H 2 O f. NaBH 4 , CH 3 OH k. CrO 3 , H 2 SO 4

b. OH, CH 2 = O, H 2 O g. H 2 , Pd-C l. Br 2 , CH 3 COOH

c. [ 1 ] LDA; [ 2 ] CH 3 CHO ; [ 3 ] H 2 O h. HOCH 2 CH 2 OH, TsOH m. Ph 3 P = CH 2

d. CH 2 ( CO 2 Et ) 2 , NaOEt, EtOH i. CH 3 NH 2 , mild acid n. NaCN, HCl

e. [ 1 ] CH 3 Li; [ 2 ] H 2 O j. ( CH 3 ) 2 NH , mild acid o. [ 1 ] LDA; [ 2 ] CH 3 I

Expert Solution
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Interpretation Introduction

(a)

Interpretation: The organic product formed when CH3CH2CH2CHO is treated with the given reagent is to be drawn.

Concept introduction: The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of products with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 24.48P

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is given below.

Organic Chemistry, Chapter 24, Problem 24.48P , additional homework tip  1

Explanation of Solution

The chemical equation when CH3CH2CH2CHO is treated with the given reagent is shown below.

Organic Chemistry, Chapter 24, Problem 24.48P , additional homework tip  2

Figure 1

The above equation shows that two equivalents of butanal is treated with OH and H2O to form a target molecule.

Conclusion

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is shown in Figure 1.

Expert Solution
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Interpretation Introduction

(b)

Interpretation: The organic product formed when CH3CH2CH2CHO is treated with the given reagent is to be drawn.

Concept introduction: The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of products with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 24.48P

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is given below.

Organic Chemistry, Chapter 24, Problem 24.48P , additional homework tip  3

Explanation of Solution

The chemical equation when CH3CH2CH2CHO is treated with the given reagent is shown below.

Organic Chemistry, Chapter 24, Problem 24.48P , additional homework tip  4

Figure 2

The above equation shows that butanal is treated with OH, CH2=O and H2O to form a target molecule.

Conclusion

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is shown in Figure 2.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The organic product formed when CH3CH2CH2CHO is treated with the given reagent is to be drawn.

Concept introduction: The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of products with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 24.48P

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is given below.

Organic Chemistry, Chapter 24, Problem 24.48P , additional homework tip  5

Explanation of Solution

The chemical equation when CH3CH2CH2CHO is treated with the given reagent is shown below.

Organic Chemistry, Chapter 24, Problem 24.48P , additional homework tip  6

Figure 3

The above equation shows that butanal is treated with LDA, CH3CHO and H2O to form a target molecule.

Conclusion

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is shown in Figure 3.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation: The organic product formed when CH3CH2CH2CHO is treated with the given reagent is to be drawn.

Concept introduction: The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of products with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 24.48P

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is given below.

Organic Chemistry, Chapter 24, Problem 24.48P , additional homework tip  7

Explanation of Solution

The chemical equation when CH3CH2CH2CHO is treated with the given reagent is shown below.

Organic Chemistry, Chapter 24, Problem 24.48P , additional homework tip  8

Figure 4

The above equation shows that butanal is treated with CH2(CO2Et)2, NaOEt and EtOH to form a target molecule.

Conclusion

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is shown in Figure 4.

Expert Solution
Check Mark
Interpretation Introduction

(e)

Interpretation: The organic product formed when CH3CH2CH2CHO is treated with the given reagent is to be drawn.

Concept introduction: The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of products with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 24.48P

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is given below.

Organic Chemistry, Chapter 24, Problem 24.48P , additional homework tip  9

Explanation of Solution

The chemical equation when CH3CH2CH2CHO is treated with the given reagent is shown below.

Organic Chemistry, Chapter 24, Problem 24.48P , additional homework tip  10

Figure 5

The above equation shows that butanal is treated with CH3Li and H2O to form a target molecule.

Conclusion

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is shown in Figure 5.

Expert Solution
Check Mark
Interpretation Introduction

(f)

Interpretation: The organic product formed when CH3CH2CH2CHO is treated with the given reagent is to be drawn.

Concept introduction: The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of products with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 24.48P

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is CH3CH2CH2CH2OH.

Explanation of Solution

The chemical equation when CH3CH2CH2CHO is treated with the given reagent is shown below.

CH3CH2CH2CHOCH3OHNaBH4CH3CH2CH2CH2OH

The above equation shows that butanal is treated with NaBH4 and CH3OH to form a target molecule. The products formed is CH3CH2CH2CH2OH.

Conclusion

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is CH3CH2CH2CH2OH.

Expert Solution
Check Mark
Interpretation Introduction

(g)

Interpretation: The organic product formed when CH3CH2CH2CHO is treated with the given reagent is to be drawn.

Concept introduction: The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of products with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 24.48P

The organic product does not form when butanal is treated with the given reagent.

Explanation of Solution

The chemical equation when CH3CH2CH2CHO is treated with the given reagent is shown below.

CH3CH2CH2CHOPd-CH2Noreaction

The above equation shows that butanal does not form any product when it is treated with hydrogen in the presence of PdC. The reaction does not take place because palladium does not reduce carbonyl compounds.

Conclusion

The reaction does not take place when butanal is treated with the given reagent.

Expert Solution
Check Mark
Interpretation Introduction

(h)

Interpretation: The organic product formed when CH3CH2CH2CHO is treated with the given reagent is to be drawn.

Concept introduction: The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of products with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 24.48P

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is given below.

Organic Chemistry, Chapter 24, Problem 24.48P , additional homework tip  11

Explanation of Solution

The chemical equation when CH3CH2CH2CHO is treated with the given reagent is shown below.

Organic Chemistry, Chapter 24, Problem 24.48P , additional homework tip  12

Figure 6

The above equation shows that butanal is treated with HOCH2CH2OH and TsOH to form a target molecule.

Conclusion

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is shown in Figure 6.

Expert Solution
Check Mark
Interpretation Introduction

(i)

Interpretation: The product formed when CH3CH2CH2MgBr is treated with the given compound is to be drawn.

Concept introduction: The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of products with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 24.48P

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is CH3CH2CH2CH=NCH3.

Explanation of Solution

The chemical equation when CH3CH2CH2CHO is treated with the given reagent is shown below.

CH3CH2CH2CHOMildacidCH3NH2CH3CH2CH2CH=NCH3

The above equation shows that butanalreacts with CH3NH2 in the presence of a mild acid to form a target molecule. The product formed is CH3CH2CH2CH=NCH3.

Conclusion

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is CH3CH2CH2CH=NCH3.

Expert Solution
Check Mark
Interpretation Introduction

(j)

Interpretation: The organic product formed when CH3CH2CH2CHO is treated with the given reagent is to be drawn.

Concept introduction: The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of products with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 24.48P

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is CH3CH2CH=CHN(CH3)2.

Explanation of Solution

The chemical equation when CH3CH2CH2CHO is treated with the given reagent is shown below.

CH3CH2CH2CHOMildacid(CH3)2NH2CH3CH2CH=CHN(CH3)2

The above equation shows that butanal reacts with (CH3)2NH2 in the presence of a mild acid to form a target molecule. The product formed is CH3CH2CH=CHN(CH3)2.

Conclusion

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is CH3CH2CH=CHN(CH3)2.

Expert Solution
Check Mark
Interpretation Introduction

(k)

Interpretation: The organic product formed when CH3CH2CH2CHO is treated with the given reagent is to be drawn.

Concept introduction: The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of products with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 24.48P

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is CH3CH2CH2COOH.

Explanation of Solution

The chemical equation when CH3CH2CH2CHO is treated with the given reagent is shown below.

CH3CH2CH2CHOH2SO4CrO3CH3CH2CH2COOH

The above equation shows that butanal reacts with CrO3 in the presence of sulphuric acid to form a target molecule. The product formed is CH3CH2CH2COOH.

Conclusion

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is CH3CH2CH2COOH.

Expert Solution
Check Mark
Interpretation Introduction

(l)

Interpretation: The organic product formed when CH3CH2CH2CHO is treated with the given reagent is to be drawn.

Concept introduction: The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of products with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 24.48P

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is given below.

Organic Chemistry, Chapter 24, Problem 24.48P , additional homework tip  13

Explanation of Solution

The chemical equation when CH3CH2CH2CHO is treated with the given reagent is shown below.

Organic Chemistry, Chapter 24, Problem 24.48P , additional homework tip  14

Figure 7

The above equation shows that butanal reacts with Br2 in the presence of acetic acid to form a target molecule.

Conclusion

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is shown in Figure 7.

Expert Solution
Check Mark
Interpretation Introduction

(m)

Interpretation: The organic product formed when CH3CH2CH2CHO is treated with the given reagent is to be drawn.

Concept introduction: The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of products with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 24.48P

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is CH3CH2CH2CH=CH2.

Explanation of Solution

The chemical equation when CH3CH2CH2CHO is treated with the given reagent is shown below.

CH3CH2CH2CHOPh3P=CH2CH3CH2CH2CH=CH2+Ph3P=O

Figure 8

The above equation shows that butanal reacts with Ph3P=CH2 to form a target molecule. The product formed is CH3CH2CH2CH=CH2.

Conclusion

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is CH3CH2CH2CH=CH2.

Expert Solution
Check Mark
Interpretation Introduction

(n)

Interpretation: The organic product formed when CH3CH2CH2CHO is treated with the given reagent is to be drawn.

Concept introduction: The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of products with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 24.48P

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is given below.

Organic Chemistry, Chapter 24, Problem 24.48P , additional homework tip  15

Explanation of Solution

The chemical equation when CH3CH2CH2CHO is treated with the given reagent is shown below.

Organic Chemistry, Chapter 24, Problem 24.48P , additional homework tip  16

Figure 8

The above equation shows that butanal reacts with NaCN in the presence of HCl to form a target molecule.

Conclusion

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is shown in Figure 8.

Expert Solution
Check Mark
Interpretation Introduction

(o)

Interpretation: The organic product formed when CH3CH2CH2CHO is treated with the given reagent is to be drawn.

Concept introduction: The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of products with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 24.48P

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is given below.

Organic Chemistry, Chapter 24, Problem 24.48P , additional homework tip  17

Explanation of Solution

The chemical equation when CH3CH2CH2CHO is treated with the given reagent is shown below.

Organic Chemistry, Chapter 24, Problem 24.48P , additional homework tip  18

Figure 9

The above equation shows that butanal reacts with LDA in the presence of CH3I to form a target molecule.

Conclusion

The organic product formed when CH3CH2CH2CHO is treated with the given reagent is shown in Figure 9.

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Chapter 24 Solutions

Organic Chemistry

Ch. 24 - Prob. 24.11PCh. 24 - Prob. 24.12PCh. 24 - Prob. 24.13PCh. 24 - Prob. 24.14PCh. 24 - Problem 24.16 What ester is formed when each...Ch. 24 - What crossed Claisen product is formed from each...Ch. 24 - Prob. 24.17PCh. 24 - Draw the products of each reaction. a. b. Ch. 24 - Problem 24.20 Two steps in a synthesis of the...Ch. 24 - Prob. 24.20PCh. 24 - Problem 24.22 Which of the following compounds can...Ch. 24 - What product is formed when each pair of compounds...Ch. 24 - Problem 24.24 What starting materials are needed...Ch. 24 - Problem 24.25 Draw the products when each pair of...Ch. 24 - Problem 24.27 What starting materials are needed...Ch. 24 - Prob. 24.26PCh. 24 - 24.29 What steps are needed to convert A to B? Ch. 24 - Prob. 24.28PCh. 24 - Prob. 24.29PCh. 24 - 24.31 Draw the product formed in each directed...Ch. 24 - Prob. 24.31PCh. 24 - What starting materials are needed to synthesize...Ch. 24 - Prob. 24.33PCh. 24 - Prob. 24.34PCh. 24 - Prob. 24.35PCh. 24 - 24.36 Identify the structures of C and D in the...Ch. 24 - Prob. 24.37PCh. 24 - Prob. 24.38PCh. 24 - Prob. 24.39PCh. 24 - Draw the product formed from a Claisen reaction...Ch. 24 - Prob. 24.41PCh. 24 - 24.41 Even though B contains three ester groups, a...Ch. 24 - Prob. 24.43PCh. 24 - What starting materials are needed to prepare each...Ch. 24 - 24.44 Vetivone is isolated from vetiver, a...Ch. 24 - Draw the product of each Robinson annulation from...Ch. 24 - Prob. 24.47PCh. 24 - Draw the organic products formed when butanal...Ch. 24 - 24.47 Draw the organic products formed in each...Ch. 24 - 24.48 Fill in the lettered reagents needed for...Ch. 24 - Prob. 24.51PCh. 24 - Prob. 24.52PCh. 24 - Prob. 24.53PCh. 24 - Draw a stepwise mechanism for the following...Ch. 24 - Prob. 24.55PCh. 24 - Prob. 24.56PCh. 24 - Prob. 24.57PCh. 24 - Prob. 24.58PCh. 24 - Prob. 24.59PCh. 24 - Prob. 24.60PCh. 24 - Prob. 24.61PCh. 24 - Prob. 24.62PCh. 24 - Devise a synthesis of each compound from...Ch. 24 - Prob. 24.64PCh. 24 - Prob. 24.65PCh. 24 - Prob. 24.66PCh. 24 - 24.65 Answer the following questions about...Ch. 24 - Prob. 24.68PCh. 24 - Prob. 24.69PCh. 24 - Prob. 24.70PCh. 24 - Prob. 24.71PCh. 24 - 24.70 Draw a stepwise mechanism for the following...Ch. 24 - Prob. 24.73PCh. 24 - Prob. 24.74PCh. 24 - Prob. 24.75P
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