Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 25, Problem 25.65P
Interpretation Introduction

(a)

Interpretation: The organic product that is formed in the given reaction is to be determined.

Concept introduction: The various organic reactions form different organic products with the help of the variety of reagents. Some of the organic compounds are formed by the characteristic action of the various functional groups present in them.

Expert Solution
Check Mark

Answer to Problem 25.65P

The product of the given reaction is,

Organic Chemistry, Chapter 25, Problem 25.65P , additional homework tip  1

Explanation of Solution

The product formed by the reaction of the given haloalkane with excess of ammonia is shown as,

Organic Chemistry, Chapter 25, Problem 25.65P , additional homework tip  2

Figure 1

In the given reaction, nitrogen present in ammonia acts as a nucleophile and attacks at carbon atom which is directly attached with electronegative chlorine atom. Chlorine ion being a good leaving group, leaves the reactant site simultaneously which results in the formation of a desired amine product.

Conclusion

The product of the given reaction is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation: The organic product that is formed in the given reaction is to be determined.

Concept introduction: The various organic reactions form different organic products with the help of the variety of reagents. Some of the organic compounds are formed by the characteristic action of the various functional groups present in them.

Expert Solution
Check Mark

Answer to Problem 25.65P

The product of the given reaction is (CH3)2CHCH2NH2.

Explanation of Solution

The product formed by the reaction of the given reactant with KOH and (CH3)2CHCH2Cl in the presence of a base is shown as,

Organic Chemistry, Chapter 25, Problem 25.65P , additional homework tip  3

Figure 2

In the given reaction, nitrogen present in the given reaction is firstly reacts with KOH to form an intermediate. The intermediate is then reacts with (CH3)2CHCH2Cl. Chlorine ion being a good leaving group, leaves the reactant site simultaneously which results in the formation of a desired amine product.

Conclusion

The product of the given reaction is (CH3)2CHCH2NH2.

Interpretation Introduction

(c)

Interpretation: The organic product that is formed in the given reaction is to be determined.

Concept introduction: The various organic reactions form different organic products with the help of the variety of reagents. Some of the organic compounds are formed by the characteristic action of the various functional groups present in them.

Expert Solution
Check Mark

Answer to Problem 25.65P

The product of the given reaction is,

Organic Chemistry, Chapter 25, Problem 25.65P , additional homework tip  4

Explanation of Solution

The product formed by the reaction of given nitro compound with tin in the presence of an acid is shown as,

Organic Chemistry, Chapter 25, Problem 25.65P , additional homework tip  5

Figure 3

In the given reaction, nitro group of the reactant reacts with Sn in the presence of hydrochloric acid to form a desired amine product.

Conclusion

The product of the given reaction is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation: The organic product that is formed in the given reaction is to be determined.

Concept introduction: The various organic reactions form different organic products with the help of the variety of reagents. Some of the organic compounds are formed by the characteristic action of the various functional groups present in them.

Expert Solution
Check Mark

Answer to Problem 25.65P

The product of the given reaction is,

Organic Chemistry, Chapter 25, Problem 25.65P , additional homework tip  6

Explanation of Solution

The product formed by the reaction of given cyano compound with LiAlH4 in the presence of water is shown as,

Organic Chemistry, Chapter 25, Problem 25.65P , additional homework tip  7

Figure 4

In the given reaction, cyano group of the reactant reacts with lithium aluminum hydride that results in the reduction of cyano group into an amino group in the presence of water. Thus, lithium aluminum hydride being a strong reducing agent forms a desired amine product.

Conclusion

The product of the given reaction is shown in Figure 4.

Interpretation Introduction

(e)

Interpretation: The organic product that is formed in the given reaction is to be determined.

Concept introduction: The various organic reactions form different organic products with the help of the variety of reagents. Some of the organic compounds are formed by the characteristic action of the various functional groups present in them.

Expert Solution
Check Mark

Answer to Problem 25.65P

The product of the given reaction is,

Organic Chemistry, Chapter 25, Problem 25.65P , additional homework tip  8

Explanation of Solution

The product formed by the reaction of given amide compound with LiAlH4 in the presence of water is shown as,

Organic Chemistry, Chapter 25, Problem 25.65P , additional homework tip  9

Figure 5

In the given reaction, amide group of the reactant reacts with lithium aluminum hydride that results in the reduction of amide group into an amino group in the presence of water. Thus, lithium aluminum hydride being a strong reducing agent forms a desired amine product.

Conclusion

The product of the given reaction is shown in Figure 5.

Interpretation Introduction

(f)

Interpretation: The organic product that is formed in the given reaction is to be determined.

Concept introduction: The various organic reactions form different organic products with the help of the variety of reagents. Some of the organic compounds are formed by the characteristic action of the various functional groups present in them.

Expert Solution
Check Mark

Answer to Problem 25.65P

The product of the given reaction is,

Organic Chemistry, Chapter 25, Problem 25.65P , additional homework tip  10

Explanation of Solution

The product formed by the reaction of given amine compound with an anhydride is shown as,

Organic Chemistry, Chapter 25, Problem 25.65P , additional homework tip  11

Figure 6

In the given reaction, amine group of the reactant reacts with the anhydride to form a desired amide product. This amide product is a secondary amide.

Conclusion

The product of the given reaction is shown in Figure 6.

Interpretation Introduction

(g)

Interpretation: The organic product that is formed in the given reaction is to be determined.

Concept introduction: The various organic reactions form different organic products with the help of the variety of reagents. Some of the organic compounds are formed by the characteristic action of the various functional groups present in them.

Expert Solution
Check Mark

Answer to Problem 25.65P

The product of the given reaction is,

Organic Chemistry, Chapter 25, Problem 25.65P , additional homework tip  12

Explanation of Solution

The product formed by the reaction of given cyclic secondary amine with sodium nitrite in the presence of an acid is shown as,

Organic Chemistry, Chapter 25, Problem 25.65P , additional homework tip  13

Figure 7

In the given reaction, amine group of the reactant reacts with NaNO2 in the presence of hydrochloric acid to form a desired N-nitrosoamine product.

Conclusion

The product of the given reaction is shown in Figure 7.

Interpretation Introduction

(h)

Interpretation: The organic product that is formed in the given reaction is to be determined.

Concept introduction: The various organic reactions form different organic products with the help of the variety of reagents. Some of the organic compounds are formed by the characteristic action of the various functional groups present in them.

Expert Solution
Check Mark

Answer to Problem 25.65P

The product of the given reaction is,

Organic Chemistry, Chapter 25, Problem 25.65P , additional homework tip  14

Explanation of Solution

The product formed by the reaction of given cyclic secondary amine with an aldehyde in the presence of NaBH3CN is shown as,

Organic Chemistry, Chapter 25, Problem 25.65P , additional homework tip  15

Figure 8

In the given reaction, amine group of the reactant reacts with benzaldehyde in the presence of NaBH3CN to form a desired N-substituted amine product.

Conclusion

The product of the given reaction is shown in Figure 8.

Interpretation Introduction

(i)

Interpretation: The organic product that is formed in the given reaction is to be determined.

Concept introduction: The various organic reactions form different organic products with the help of the variety of reagents. Some of the organic compounds are formed by the characteristic action of the various functional groups present in them.

Expert Solution
Check Mark

Answer to Problem 25.65P

The product of the given reaction is,

Organic Chemistry, Chapter 25, Problem 25.65P , additional homework tip  16

Explanation of Solution

The product formed by the reaction of given cyclic amine compound with an cyclic ketonic compound is shown as,

Organic Chemistry, Chapter 25, Problem 25.65P , additional homework tip  17

Figure 9

In the given reaction, amine group of the reactant reacts with a cyclic ketonic compound to form a desired product.

Conclusion

The product of the given reaction is shown in Figure 9.

Interpretation Introduction

(j)

Interpretation: The organic product that is formed in the given reaction is to be determined.

Concept introduction: The various organic reactions form different organic products with the help of the variety of reagents. Some of the organic compounds are formed by the characteristic action of the various functional groups present in them.

Expert Solution
Check Mark

Answer to Problem 25.65P

The product of the given reaction is CH3CH=CH2.

Explanation of Solution

The product formed by the reaction of given secondary amine compound with methyl iodide in the presence of Ag2O and deuterium is shown as,

Organic Chemistry, Chapter 25, Problem 25.65P , additional homework tip  18

Figure 10

In the given reaction, amine group of the reactant reacts with CH3I in the presence of silver oxide followed by the heating. This reaction results in the formation of an alkene as a desired product and release of a quaternary ammonium salt.

Conclusion

The product of the given reaction is CH3CH=CH2.

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Chapter 25 Solutions

Organic Chemistry

Ch. 25 - Prob. 25.11PCh. 25 - Prob. 25.12PCh. 25 - Prob. 25.13PCh. 25 - Prob. 25.14PCh. 25 - Prob. 25.15PCh. 25 - Prob. 25.16PCh. 25 - Prob. 25.17PCh. 25 - Prob. 25.18PCh. 25 - Draw the products of each acidbase reaction....Ch. 25 - Prob. 25.20PCh. 25 - Prob. 25.21PCh. 25 - Prob. 25.22PCh. 25 - Prob. 25.23PCh. 25 - Problem 25.22 Which nitrogen atom in each compound...Ch. 25 - Which N atom in each drug is more basic? a. b. c.Ch. 25 - Prob. 25.26PCh. 25 - Prob. 25.27PCh. 25 - Prob. 25.28PCh. 25 - Prob. 25.29PCh. 25 - Prob. 25.30PCh. 25 - Problem 25.28 Draw the major product formed in...Ch. 25 - Prob. 25.32PCh. 25 - Prob. 25.33PCh. 25 - Problem 25.31 Devise a synthesis of each compound...Ch. 25 - Prob. 25.35PCh. 25 - Problem 25.33 What starting materials are needed...Ch. 25 - Problem 25.34 (a) What two components are needed...Ch. 25 - Prob. 25.38PCh. 25 - Prob. 25.39PCh. 25 - Prob. 25.40PCh. 25 - 25.37 Varenicline (trade name Chantix) is a drug...Ch. 25 - Prob. 25.42PCh. 25 - Prob. 25.43PCh. 25 - Prob. 25.44PCh. 25 - Prob. 25.45PCh. 25 - Prob. 25.46PCh. 25 - Prob. 25.47PCh. 25 - Prob. 25.48PCh. 25 - Decide which N atom in each molecule is most basic...Ch. 25 - 25.44 Rank the nitrogen atoms in each compound in...Ch. 25 - 25.45 Explain why nitroaniline is a stronger base...Ch. 25 - 25.46 Explain the observed difference in the...Ch. 25 - 25.47 Why is pyrrole more acidic than...Ch. 25 - How would you prepare 3-phenyl-1-propanamine...Ch. 25 - Prob. 25.55PCh. 25 - Prob. 25.56PCh. 25 - Prob. 25.57PCh. 25 - Prob. 25.58PCh. 25 - 25.51 How would you separate toluene , benzoic...Ch. 25 - 25.52 Draw the products formed when methylaniline ...Ch. 25 - Prob. 25.61PCh. 25 - Prob. 25.62PCh. 25 - Prob. 25.63PCh. 25 - Prob. 25.64PCh. 25 - Prob. 25.65PCh. 25 - Prob. 25.66PCh. 25 - Prob. 25.67PCh. 25 - Prob. 25.68PCh. 25 - 25.60 A chiral amine A having the configuration...Ch. 25 - 25.61 Draw a stepwise mechanism for each...Ch. 25 - 25.62 Draw a stepwise mechanism for the following...Ch. 25 - Prob. 25.72PCh. 25 - Tertiary (3) aromatic amines react with NaNO2 and...Ch. 25 - Prob. 25.74PCh. 25 - Devise a synthesis of each compound from benzene....Ch. 25 - Prob. 25.76PCh. 25 - Prob. 25.77PCh. 25 - Prob. 25.78PCh. 25 - Prob. 25.79PCh. 25 - Synthesize each compound from benzene. Use a...Ch. 25 - Prob. 25.81PCh. 25 - Devise a synthesis of each compound from benzene,...Ch. 25 - Prob. 25.83PCh. 25 - 25.72 Three isomeric compounds A, B, and C, all...Ch. 25 - 25.73 Treatment of compound D with LiAlH4 followed...Ch. 25 - Prob. 25.86PCh. 25 - 25.75 Rank the following compounds in order of...Ch. 25 - Prob. 25.88PCh. 25 - Prob. 25.89PCh. 25 - Prob. 25.90P
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