Textbook Question
Draw Newman projections of the following molecules viewed from the direction of the blue arrows.
(b)
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Ch.3 - Structure and Stereochemistry of Alkanes
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 3, Problem 11c
Draw Newman projections of the following molecules viewed from the direction of the blue arrows.
(c) 
Verified step by step guidance1
Identify the molecule and the specific bond you are viewing along the direction of the blue arrow. Newman projections are typically used to visualize the conformation around a single bond, so it's crucial to know which bond you are focusing on.
Determine the front and back carbon atoms along the bond you are viewing. The front carbon is the one closest to you, and the back carbon is the one further away.
Draw a circle to represent the back carbon atom. This circle will help you visualize the spatial arrangement of the substituents attached to the back carbon.
Draw three lines radiating from the center of the circle to represent the substituents attached to the back carbon. These lines should be evenly spaced at 120 degrees apart, forming a 'Y' shape within the circle.
Draw the front carbon atom as a point in front of the circle. From this point, draw three lines radiating outward to represent the substituents attached to the front carbon. These lines should also be spaced at 120 degrees apart, forming a 'Y' shape. Ensure that the substituents on the front carbon do not overlap with those on the back carbon, as this will help visualize the staggered or eclipsed conformation.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Newman Projection
A Newman projection is a way of drawing a molecule to show the conformation of a carbon-carbon bond. It is viewed along the axis of the bond, with the front carbon represented by a dot and the back carbon by a circle. This perspective helps visualize the spatial arrangement of substituents around the bond, which is crucial for understanding steric interactions and conformational isomerism.
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00:34
Introduction to Drawing Newman Projections
Conformational Isomerism
Conformational isomerism refers to the different spatial arrangements of atoms that result from rotation around a single bond. These isomers, or conformers, can interconvert through such rotations, affecting the molecule's energy and stability. Understanding conformational isomerism is essential for predicting the most stable conformation of a molecule, which is often depicted using Newman projections.
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03:29Understanding what a conformer is.
Steric Hindrance
Steric hindrance occurs when atoms or groups within a molecule are positioned in such a way that they physically impede each other's space, leading to increased energy and decreased stability. In Newman projections, steric hindrance is visualized by the proximity of substituents on adjacent carbons, influencing the preferred conformation of the molecule.
Recommended video:
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02:53Understanding steric effects.
Related Practice
Textbook Question
List each set of compounds in order of increasing boiling point.
b. Octane, (CH3)3C—C(CH3)3 and CH3CH2C(CH3)2CH2CH2CH3
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Textbook Question
Draw a graph, similar to Figure 3-9, of the torsional strain of 2-methylpropane as it rotates about the bond between C1 and C2. Show the dihedral angle and draw a Newman projection for each staggered and eclipsed conformation.
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Textbook Question
Draw a perspective representation of the most stable conformation of 3-methylhexane.
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Textbook Question
Draw Newman projections of the following molecules viewed from the direction of the blue arrows.
(a)
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Textbook Question
Draw a graph, similar to Figure 3-11, of the torsional energy of 2-methylbutane as it rotates about the C2—C3 bond.
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