Chapter 11: Problem 17
Draw Newman projections of the staggered and eclipsed conformations of propane. Rank them in stability.
Short Answer
Expert verified
The staggered conformation of propane, when viewed using Newman projections, is more stable than the eclipsed conformation. The ranking in terms of stability is: Staggered > Eclipsed.
Step by step solution
01
Understanding the Concept of Conformations
In the context of organic chemistry, different conformations of a molecule are achieved by rotating around a single bond. For propane, which is a linear three carbon compound, there are mainly two types of conformations - staggered and eclipsed. In the staggered conformation, the hydrogen atoms of adjacent carbons are as far apart as possible, whereas in the eclipsed conformation, they are as close as possible.
02
Drawing Newman Projections of Propane
Newman projections are a way to view a molecule from a certain angle, usually straight down a specific bond. In the case of propane, start by looking down the C1-C2 bond. For staggered conformation, one hydrogen atom on C1 aligns with a hydrogen atom on C2 in the front view, then the three hydrogen atoms on C2 are placed so that they fall between and not behind the hydrogens in the front view. For eclipsed conformation, the three hydrogen atoms on C2 are placed exactly behind the hydrogens in the front view.
03
Ranking Stabilities of Conformations
The stabilities of different conformations are determined by their potential energy. The staggered conformation of propane is the most stable because it minimizes electron repulsion among hydrogen atoms. On the other hand, the eclipsed conformation is less stable because the hydrogen atoms are closer to each other leading to more electron repulsion. So the stability ranking from most stable to least stable is: Staggered > Eclipsed.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Conformations in Organic Chemistry
In organic chemistry, the spatial arrangement of atoms within a molecule can vary without breaking any chemical bonds, resulting in different conformations. Each conformation is like a snapshot of the molecule's shape at a particular moment as it rotates around its bonds. These subtle changes in orientation can have a significant impact on the molecule's chemical properties and reactions. For example, when analyzing propane, a simple alkane with three carbon atoms, the carbon-carbon single bonds allow rotation, leading to multiple conformations. Understanding these conformations is key to predicting reaction outcomes and physical properties of organic compounds. The study of molecular conformations is crucial for students as it lays the foundation for comprehending more complex molecular structures and reaction mechanisms.
Staggered and Eclipsed Conformations
Focusing on the Newman projections of propane required for this problem, there are two principal conformations to consider: staggered and eclipsed. When visualizing these conformations, imagine yourself looking down the bond between two carbon atoms. In the staggered conformation, the hydrogen atoms attached to the adjacent carbon atoms are positioned at angles to each other, minimizing repulsion; it's akin to runners on a track staying in their lanes. Conversely, the eclipsed conformation aligns the hydrogens directly behind each other, as if the runners were all scrambling in a single line - this proximity leads to increased repulsion between electron clouds.
In drawing the Newman projections, it's essential to place the hydrogen atoms correctly relative to each other to represent each conformation accurately. Students often find it helpful to imagine turning a two-bladed propeller where the blades represent hydrogen atoms: in a staggered position, the blades are in their most separated state, while in an eclipsed position, they cover each other's silhouette.
In drawing the Newman projections, it's essential to place the hydrogen atoms correctly relative to each other to represent each conformation accurately. Students often find it helpful to imagine turning a two-bladed propeller where the blades represent hydrogen atoms: in a staggered position, the blades are in their most separated state, while in an eclipsed position, they cover each other's silhouette.
Stability Ranking of Conformations
The concept of stability in molecular conformations hinges on the potential energy of each conformation. Energy is a currency molecules use, preferring to save rather than spend. Thus, the staggered conformation, where hydrogens are spaced out, leads to lower energy expenditure due to reduced electron cloud repulsion. This configuration is the molecular equivalent of relaxation. In contrast, the eclipsed conformation resembles a state of tension, with hydrogens closely facing each other, which increases potential energy due to the higher repulsive forces involved.
As a rule, lower potential energy corresponds to greater stability. Therefore, when ranking the conformations, the staggered conformation stands as the more stable arrangement for propane, followed by the eclipsed conformation. This hierarchy of stability is integral to understanding molecular dynamics and factors in the outcomes of chemical reactions. It’s a cornerstone for any student delving into organic chemistry.
As a rule, lower potential energy corresponds to greater stability. Therefore, when ranking the conformations, the staggered conformation stands as the more stable arrangement for propane, followed by the eclipsed conformation. This hierarchy of stability is integral to understanding molecular dynamics and factors in the outcomes of chemical reactions. It’s a cornerstone for any student delving into organic chemistry.