Br NINH, DMSO 45 °C NaOCH₂ CH₂OH reflux H₂O A

Chemistry
10th Edition
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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1. Predicting the product of a chemical reaction is a valuable skill to learn so the time does not have to be taken to write
the full mechanism of each reaction. Each type of reaction has a slightly different approach to predicting the product
due to the different mechanism. Here is a plan of action for predicting the outcome of elimination reactions.
E2 predicting the products:
a. Identify the ß-hydrogens and leaving group.
i. If the base is small, use the B-hydrogen in the more substituted position.
ii. If the base is bulky, use the B-hydrogen in the less substituted position.
LG
CI
b Orient the B-hydrogen anti to the leaving group.
E1 predicting the products:
H
c. Remove the B-hydrogen and leaving group, replacing it with a x-bond between a and B.
Br
Br
H
HHH
B-hydrogens
BuOH
reflux
a. Remove the leaving group to form a carbocation and investigate for carbocation rearrangements.
NaNH,
DMSO
45 °C
b. Identify the ß-hydrogens and leaving group.
i. If the base is small, use the B-hydrogen in the more substituted position.
ii. If the base is bulky, use the B-hydrogen in the less substituted position.
NaOCH3
CH₂OH
reflux
H₂O
A
small base
NaOH
heat
Liox
acetone
E
LG
CI
Br
major organic product
d. Remove the B-hydrogen, replacing it with a -bond between a (where the carbocation is located) and B. If E or Z
alkenes could be made, E is preferred.
DBU
acetonitrile
bulky base
Using the method noted on the previous page, predict the major organic product of the following elimination
reactions. Think through if they are unimolecular or bimolecular based on the a-carbon, base strength, and
solvent.
HHHH
major organic product
H
H
B-hydrogens
H
Transcribed Image Text:1. Predicting the product of a chemical reaction is a valuable skill to learn so the time does not have to be taken to write the full mechanism of each reaction. Each type of reaction has a slightly different approach to predicting the product due to the different mechanism. Here is a plan of action for predicting the outcome of elimination reactions. E2 predicting the products: a. Identify the ß-hydrogens and leaving group. i. If the base is small, use the B-hydrogen in the more substituted position. ii. If the base is bulky, use the B-hydrogen in the less substituted position. LG CI b Orient the B-hydrogen anti to the leaving group. E1 predicting the products: H c. Remove the B-hydrogen and leaving group, replacing it with a x-bond between a and B. Br Br H HHH B-hydrogens BuOH reflux a. Remove the leaving group to form a carbocation and investigate for carbocation rearrangements. NaNH, DMSO 45 °C b. Identify the ß-hydrogens and leaving group. i. If the base is small, use the B-hydrogen in the more substituted position. ii. If the base is bulky, use the B-hydrogen in the less substituted position. NaOCH3 CH₂OH reflux H₂O A small base NaOH heat Liox acetone E LG CI Br major organic product d. Remove the B-hydrogen, replacing it with a -bond between a (where the carbocation is located) and B. If E or Z alkenes could be made, E is preferred. DBU acetonitrile bulky base Using the method noted on the previous page, predict the major organic product of the following elimination reactions. Think through if they are unimolecular or bimolecular based on the a-carbon, base strength, and solvent. HHHH major organic product H H B-hydrogens H
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