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Ch. 19 - Amines
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook
All textbooksWade 9th EditionCh. 19 - AminesProblem 51c
Chapter 19, Problem 51c

Using any necessary reagents, show how you can accomplish the following multistep syntheses.
(c)

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1
Step 1: Begin by identifying the target molecule and the starting material. The starting material is biphenyl, and the target molecule has two functional groups added: an ethyl group (-CH2CH3) and an aminomethyl group (-CH2NH2).
Step 2: Introduce the ethyl group onto one of the benzene rings of biphenyl. This can be achieved through Friedel-Crafts alkylation using ethyl chloride (CH3CH2Cl) and a Lewis acid catalyst such as AlCl3. This reaction selectively adds the ethyl group to the benzene ring.
Step 3: Introduce the aminomethyl group (-CH2NH2) onto the other benzene ring. This can be done by first performing a chloromethylation reaction using formaldehyde (HCHO) and hydrochloric acid (HCl) to add a chloromethyl group (-CH2Cl).
Step 4: Convert the chloromethyl group (-CH2Cl) into an aminomethyl group (-CH2NH2) by treating the intermediate with ammonia (NH3) in a nucleophilic substitution reaction. This replaces the chlorine atom with an amino group.
Step 5: Verify the structure of the final product to ensure that the ethyl group and aminomethyl group are correctly positioned on the biphenyl framework. This completes the synthesis.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Multistep Synthesis

Multistep synthesis involves a series of chemical reactions that transform starting materials into a desired product through intermediate compounds. Each step typically requires specific reagents and conditions, and understanding the sequence of reactions is crucial for successful synthesis. This concept is fundamental in organic chemistry for constructing complex molecules from simpler ones.
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Reduction Reactions

Reduction reactions involve the gain of electrons or hydrogen, or the loss of oxygen, resulting in the conversion of a compound to a more reduced state. In organic chemistry, this often refers to the transformation of carbonyl groups to alcohols or the reduction of nitro groups to amines. Recognizing the appropriate reducing agents, such as lithium aluminum hydride or hydrogen gas with a catalyst, is essential for executing these reactions.
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Functional Group Transformation

Functional group transformation refers to the process of converting one functional group into another, which is a key aspect of organic synthesis. In the provided reaction, an aromatic compound is transformed to introduce an ethyl group and an amine group. Understanding how different functional groups react and the conditions required for their transformation is vital for designing effective synthetic pathways.
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Related Practice
Textbook Question

Pyrrole undergoes electrophilic aromatic substitution more readily than benzene, and mild reagents and conditions are sufficient. These reactions normally occur at the 2-position rather than the 3-position, as shown in the following example.

b. Explain why pyrrole reacts more readily than benzene, and also why substitution occurs primarily at the 2-position rather than the 3-position.

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Textbook Question

Show how you can synthesize the following compounds starting with benzene, toluene, and alcohols containing no more than four carbon atoms as your organic starting materials. Assume that para is the major product (and separable from ortho) in ortho, para mixtures.

(d) N-benzylpropan-1-amine

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Textbook Question

The following spectra for A and B correspond to two structural isomers. The NMR singlet at δ1.16 in spectrum A disappears when the sample is shaken with D2O. The singlet at δ0.6 ppm in the spectrum of B disappears on shaking with D2O. Propose structures for these isomers, and show how your structures correspond to the spectra. Show what cleavage is responsible for the base peak at m/z 44 in the mass spectrum of A and the prominent peak at m/z 58 in the mass spectrum of B.

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Textbook Question

Using any necessary reagents, show how you can accomplish the following multistep syntheses.

(b)

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Textbook Question

Show how you can synthesize the following compounds starting with benzene, toluene, and alcohols containing no more than four carbon atoms as your organic starting materials. Assume that para is the major product (and separable from ortho) in ortho, para mixtures.

(g) 4-isobutylaniline

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Textbook Question

Pyrrole undergoes electrophilic aromatic substitution more readily than benzene, and mild reagents and conditions are sufficient. These reactions normally occur at the 2-position rather than the 3-position, as shown in the following example.

a. Propose a mechanism for the acetylation of pyrrole just shown. You may begin with pyrrole and the acylium ion, CH3C≡O+. Be careful to draw all the resonance structures of the intermediate.

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