Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure

Bruice8th EditionOrganic ChemistryISBN: 9780135213711Not the one you use?Change textbook

Bruice 8th Edition

Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure

Problem 29e

Chapter 4, Problem 29e

Draw condensed and skeletal structures for each of the following amines:
e. N,N-dimethyl-3-pentanamine

Verified step by step guidance

Step 1: Understand the name of the compound. The name 'N,N-dimethyl-3-pentanamine' indicates that the molecule is an amine with a pentane backbone (5 carbon chain) and two methyl groups attached to the nitrogen atom. The '3-pentanamine' part specifies that the amine group (-NH2) is attached to the third carbon of the pentane chain.

Step 2: Begin by drawing the pentane backbone. Represent the 5 carbon atoms in a straight chain, labeling them as C1, C2, C3, C4, and C5.

Step 3: Place the amine group (-NH2) on the third carbon (C3). Since the name specifies 'N,N-dimethyl,' replace the two hydrogens on the nitrogen atom with two methyl groups (-CH3). This creates the N,N-dimethyl substitution.

Step 4: Draw the condensed structure. Write the molecular formula in a compact form, showing the connectivity of the atoms. For example, the condensed structure would look like CH3CH2CH(N(CH3)2)CH2CH3.

Step 5: Draw the skeletal structure. Use zigzag lines to represent the carbon chain, omitting hydrogens bonded to carbons for simplicity. Show the nitrogen atom bonded to the third carbon, with two methyl groups attached to the nitrogen. Ensure the skeletal structure clearly represents the connectivity and geometry of the molecule.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above.

Video duration:

Was this helpful?

Key Concepts

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

Amines

Amines are organic compounds derived from ammonia (NH3) by replacing one or more hydrogen atoms with alkyl or aryl groups. They can be classified as primary, secondary, or tertiary based on the number of carbon-containing groups attached to the nitrogen atom. Understanding the structure and classification of amines is essential for drawing their condensed and skeletal forms.

Condensed Structures

Condensed structures provide a simplified representation of a molecule, showing the connectivity of atoms without depicting all the bonds explicitly. In the case of amines, the condensed structure will indicate the nitrogen atom's connectivity to its substituents, allowing for a quick understanding of the molecular framework. This format is particularly useful for larger molecules where full structural formulas would be cumbersome.

Skeletal Structures

Skeletal structures, or line-angle formulas, represent organic molecules using lines to depict bonds between carbon atoms, with vertices representing carbon atoms and other elements (like nitrogen) shown explicitly. This method emphasizes the carbon backbone and is particularly useful for visualizing complex organic molecules, making it easier to identify functional groups and overall molecular geometry.

Recommended video:

Guided course

04:03

How bondline is different from Lewis Structures.

Related Practice

Textbook Question

For each of the following, give the systematic name and the common name (if it has one) and then indicate whether it is a primary, secondary, or tertiary amine:

1107

views

Textbook Question

For each of the following, give the systematic name and the common name (if it has one) and then indicate whether it is a primary, secondary, or tertiary amine:

1179

views

Textbook Question

Are the following compounds primary, secondary, or tertiary?

1909

views

Textbook Question

Draw condensed and skeletal structures for each of the following amines:

c. 5-methyl-1-hexanamine

986

views

Textbook Question