Organic Chemistry (8th Edition)

Published by Pearson
ISBN 10: 0321768418
ISBN 13: 978-0-32176-841-4

Chapter 5 - Stereochemistry - Problems - Page 197: Problem 5-15 a

Answer

First draw the allene (C=C=C), which is linear because the double bonds on with side result in sp hybridization for the central carbon. Then, add the H's and chlorine to the 1st and 3rd carbons of the propadiene. Notice that for 1 of the carbons, dash and wedge are used while the other carbon does not use it. This is because the p-orbitals of these end carbons are perpendicular; they are not in the same plane. Therefore, their substituents are also in different planes.

Work Step by Step

This molecule has no asymmetric carbon but is still chiral. See image.
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