R, CH2 „R2 C=C C=C H `H H R3 C=C CH,. ‚CH2 c=C н `H H H H R4 C=C

Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Linoleic acid is an essential fatty acid found in many veg-etable oils, such as soy, peanut, and cottonseed. A key structural feature of the molecule is the c is orientation around its two dou-ble bonds, where R1and R2 represent two different groups thatform the rest of the molecule. (a) How many different compounds are possible, changing onlythe cis-trans arrangements around these two double bonds?(b) How many are possible for a similar compound with three double bonds?

R,
CH2
„R2
C=C
C=C
H
`H H
Transcribed Image Text:R, CH2 „R2 C=C C=C H `H H
R3
C=C
CH,.
‚CH2
c=C
н
`H H
H H
R4
C=C
Transcribed Image Text:R3 C=C CH,. ‚CH2 c=C н `H H H H R4 C=C
Expert Solution
Step 1
  • Each carbon in the pi bond is attached to two substituents. For each carbon, these two substituents are ranked (1 or 2) according to the atomic numbers of the atom directly attached to the carbon. (e.g. Cl > F )
  • If both substituents ranked 1 are on the same side of the pi bond, the bond is given the descriptor Z (short for German Zusammen, which means “together”).
  • If both substituents ranked 1 are on the opposite side of the pi bond, the bond is given the descriptor (short for German Entgegen, which means “opposite”).

So Z resembles “cis” and E resembles “trans”  .  (Note:  they are not necessarily the same and do not always correlate) .The E/Z system is comprehensive for all alkenes capable of geometric isomerism, including the cis/trans alkene . We often use cis/trans for convenience, but E/Z is the “official”, IUPAC approved way to name alkene stereoisomers

 

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