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Chapter 22: Problem 24

Provide a structural formula for each of the following compounds: (a) 2-Ethyl-1-butanamine (f) \(N\) -Allylcyclohexylamine (b) \(N\) -Ethyl-1-butanamine (g) \(N\) -Allylpiperidine (c) Dibenzylamine (h) Benzyl 2-aminopropanoate (d) Tribenzylamine (i) \(4-(N, N\) -Dimethylamino) cyclohexanone (e) Tetraethylammonium hydroxide (j) 2,2 -Dimethyl-1, 3 -propanediamine

Short Answer

Expert verified
Draw structural formulas using the given nomenclature and verify correctness.

Step by step solution

01

Understanding the Nomenclature

For each compound name provided, break down the naming components: any prefix or suffix gives insight into the molecular structure. This includes identifying numbers indicative of chain length, position of molecular branches, and functional groups like amines, ester, etc.
02

Building the Carbon Backbone

Identify the main carbon chain or ring from the name: - For (a), the main chain is butane, substituted at the 2-position by an ethyl group. - For (f), cyclohexyl indicates a ring structure, etc. Draw the backbone structure for each compound.
03

Adding Branches and Functional Groups

Add any substituents like alkyl groups or amines to the carbon backbone as indicated by the compound name. - For (a) and (b), place the ethyl group at the specified position. - For amines, attach the NH or NHR group because they're primary, secondary, or tertiary amines.
04

Incorporating Double Bonds and Rings

For structures with pi bonds or rings, include these in desired positions: - For (f), place an allyl group on nitrogen by adding the double-bonded structure. - For (g), integrate the piperidine ring by drawing a six-membered ring with one nitrogen atom.
05

Finalizing and Verifying Structures

Double-check each structural formula to ensure that halogens, functional groups, and connectors (like chains and rings) are correctly placed and conform to their naming in IUPAC or common terminology. Ensure each compound has the correct number of hydrogens to satisfy each carbon's four-bond requirement.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Amines
Amines are an important class of organic compounds that serve as the nitrogen-containing counterparts to alcohols and ethers. They are characterized by the presence of a nitrogen atom bonded to one or more alkyl or aromatic groups. Depending on how many carbon chains are attached to the nitrogen atom, amines can be classified as:
  • Primary Amines: These have one carbon group attached to the nitrogen. An example from our exercise is 2-Ethyl-1-butanamine.
  • Secondary Amines: This type has two carbon groups. Dibenzylamine is an example, where two benzyl groups are connected to the nitrogen.
  • Tertiary Amines: If three carbon chains are attached, like in Tribenzylamine, it is a tertiary amine.
Each type has unique properties and chemical reactivity patterns, making them versatile in creating complex molecules.
Functional Groups
Functional groups are specific groups of atoms responsible for the characteristic reactions of a particular compound. They play a crucial role in determining the properties and reactions of organic molecules. In the context of the exercise:
  • Amino Group (鈭扤H2): Found in amines, it is a key functional group that defines their chemical nature.
  • Ester Group: Present in compounds like benzyl 2-aminopropanoate, consisting of a carbon double-bonded to oxygen ( C=O and bonded to another oxygen atom, further bonded to carbon.
  • Ketone Group: This group is present in cyclohexanone, part of the 4-(N,N-Dimethylamino) cyclohexanone structure, featuring a carbonyl group (C=O) bonded to two carbon groups.
Recognizing these groups helps predict the behavior of molecules in chemical reactions and syntheses.
IUPAC Naming
The IUPAC naming system provides a standardized way to name organic chemical compounds. This ensures each compound has a unique descriptive name, reflecting its structure. Key to naming amines and the compounds in our exercise is identifying:
  • Main Chain: The longest continuous carbon chain, which dictates the root name.
  • Substituents: Function groups or branches attached that modify the base name.
  • Numbering the Chain: Number the carbon atoms so that the key functional groups receive the lowest possible numbers.
  • Special Prefixes & Suffixes: Indicate types of functional groups or amines, like 'N-' for nitrogen substituents or '-amine' for amino groups.
This precise system reduces confusion and ensures clear communication in the scientific community.
Carbon Chain Structures
Carbon chain structures form the backbone of organic molecules. The length and branching of these chains dramatically affect the molecule's properties and reactivity. In the context of the exercise:
  • Straight Chains: Simple unbranched carbon chains as in the butane part of 2-Ethyl-1-butanamine.
  • Branched Chains: Include alkyl branches attached to the main chain, such as ethyl groups in N-Ethyl-1-butanamine.
  • Cyclic Structures: These are circular, like the cyclohexyl ring in N-Allylcyclohexylamine, offering distinct geometric and chemical properties.
Understanding the structure helps in grasping how molecules behave and interact with other chemicals.
Structural Formulas
Structural formulas provide a visual representation of a molecule, showing how atoms are arranged and bonded together. They are valuable in understanding the geometry and functionality of a compound:
  • Line Drawings: Use lines to represent bonds between atoms, often omitting hydrogen atoms for simplicity.
  • Condensed Formulas: This format displays repetitive units as groups, saving space and simplifying complex molecules' representation.
  • Expanded Formulas: Highlight every atom and bond, useful for exploring reactions and functionality intimately.
By expressing the relationship between atoms in a clear, structured way, structural formulas enable chemists to predict physical and chemical properties and reactivity patterns.

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Most popular questions from this chapter

Arrange the members of each group in order of decreasing basicity: (a) Ammonia, aniline, methylamine (b) Acetanilide, aniline, \(N\) -methylaniline (c) 2,4 -Dichloroaniline, 2,4 -dimethylaniline, 2,4 -dinitroaniline (d) 3,4-Dichloroaniline, 4-chloro-2-nitroaniline, 4 -chloro-3-nitroaniline (e) Dimethylamine, diphenylamine, \(N\) -methylaniline

Many naturally occurring nitrogen compounds and many nitrogen-containing drugs are better known by common names than by their systematic names. A few of these follow. Write a structural formula for each one. (a) trans-2-Phenylcyclopropylamine, better known as tranylcypromine an antidepressant drug (b) \(N\) -Benzyl- \(N\) -methyl-2-propynylamine, better known as pargyline a drug used to treat high blood pressure (c) 1-Phenyl-2-propanamine, better known as amphetamine a stimulant (d) 1-(m-Hydroxyphenyl)-2-(methylamino)ethanol: better known as phenylephrine a nasal decongestant

Write the structure of the product formed on reaction of aniline with each of the following: (a) Hydrogen bromide (b) Excess methyl iodide (c) Acetaldehyde (d) Acetaldehyde and hydrogen (nickel catalyst) (e) Acetic anhydride (f) Benzoyl chloride (g) Sodium nitrite, aqueous sulfuric acid, \(0-5 \mathrm{C}\)

Each of the following compounds has been prepared from \(p\) -nitroaniline. Outline a reasonable series of steps leading to each one. (a) \(p\) -Nitrobenzonitrile (b) \(3,4,5\) -Trichloroaniline (c) 1,3 -Dibromo-5-nitrobenzene (d) 3 ,5-Dibromoaniline (c) \(p\) -Acetamidophenol +acetaminophen)

Outline syntheses of each of the following from aniline and any necessary organic or inorganic reagents. (a) \(p\) -Nitroaniline (b) 2,4 -Dinitroaniline (c) \(p\) -Aminoacetanilide
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