Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
Question
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Chapter 25, Problem 25.1P
Interpretation Introduction

(a)

Interpretation: The primary, secondary or tertiary amine in the given compound is to be classified.

Concept introduction: Amines are nitrogen-containing organic compounds. The general formula of amines is RNH2. Amines can be classified as primary amine, secondary amine, and tertiary amine. In Primary amines, one of the hydrogen atoms of ammonia is replaced by alkyl or aryl group.

In secondary amines, two of the hydrogen atoms of ammonia are replaced by alkyl or aryl group.

In tertiary amines, all hydrogen atoms of ammonia are replaced by alkyl or aryl group.

Expert Solution
Check Mark

Answer to Problem 25.1P

Each amine in the given compound is classified as,

Organic Chemistry, Chapter 25, Problem 25.1P , additional homework tip  1

Explanation of Solution

The given compound is shown below.

Organic Chemistry, Chapter 25, Problem 25.1P , additional homework tip  2

Figure 1

In spermine, four nitrogen atoms are present. Among these four nitrogen atoms, two are primary amines that contain one alkyl group on nitrogen atom and two are secondary amines that contain two alkyl groups on nitrogen atom as shown below.

Organic Chemistry, Chapter 25, Problem 25.1P , additional homework tip  3

Figure 2

Conclusion

In spermine, primary and secondary amines are present as shown in Figure 2.

Interpretation Introduction

(b)

Interpretation: The primary, secondary or tertiary amine in the given compound is to be classified.

Concept introduction: Amines are nitrogen-containing organic compounds. The general formula of amines is RNH2. Amines can be classified as primary amine, secondary amine, and tertiary amine. In Primary amines, one of the hydrogen atoms of ammonia is replaced by alkyl or aryl group.

In secondary amines, two of the hydrogen atoms of ammonia are replaced by alkyl or aryl group.

In tertiary amines, all hydrogen atoms of ammonia are replaced by alkyl or aryl group.

Expert Solution
Check Mark

Answer to Problem 25.1P

Each amine in the given compound is classified as,

Organic Chemistry, Chapter 25, Problem 25.1P , additional homework tip  4

Explanation of Solution

The given compound is shown below.

Organic Chemistry, Chapter 25, Problem 25.1P , additional homework tip  5

Figure 3

Meperidine contains one nitrogen atom bonded to three alkyl groups. Hence, it is a tertiary amine as shown below.

Organic Chemistry, Chapter 25, Problem 25.1P , additional homework tip  6

Figure 4

Conclusion

In meperidine, tertiary amine is present as shown in Figure 4.

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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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