1. Orbitals and stereochemistry in the E2 reaction a. Add the orbitals and missing substituent labels to the starting material drawings below, showing orbital shading on the reactants that corresponds to the new bonds being formed (show only o* shading, although o is reacting too), then translate the alkene product perspective drawings into the corresponding flat alkene drawings. н-он он nb O(sp3) R Br Me H tBu E2 o*CH Et o*CBr Br flat drawing of alkene product Br Add Me, Et, R, and tBu labels to match the first structure add orbitals for the alkene product pi bond Add Me, Et, R, and tBu labels to match the first structure add orbitals for E2 reaction (hydroxide as base) н-он OH nb O(sp3) R Br Me H. tBu Ét E2 o*CH o*CBr Br flat drawing of alkene product Br Add Me, Et, R, and tBu labels to match the first structure add orbitals for the alkene product pi bond Add Me, Et, R, and tBu labels to match the first structure add orbitals for E2 reaction (hydroxide as base)

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter14: Elimination
Section: Chapter Questions
Problem 36CTQ
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1. Orbitals and stereochemistry in the E2 reaction
a. Add the orbitals and missing substituent labels to the starting material drawings below, showing orbital
shading on the reactants that corresponds to the new bonds being formed (show only o* shading,
although o is reacting too), then translate the alkene product perspective drawings into the corresponding
flat alkene drawings.
н-он
OH
nb O(sp3)
R Br
Me
H.
E2
tBu
o*CH
Et
o*CBr
Br
flat drawing of
alkene product
Br
add orbitals for the
Add Me, Et, R, and tBu labels
to match the first structure
alkene product pi bond
Add Me, Et, R, and tBu labels
to match the first structure
add orbitals for E2 reaction
(hydroxide as base)
H-OH
OH
nb O(sp3)
R Br
Me
H.
tBu'
E2
O*CH
Et
o*CBr
Br
flat drawing of
alkene product
Br
Add Me, Et, R, and tBu labels
to match the first structure
add orbitals for the
alkene product pi bond
add orbitals for E2 reaction
(hydroxide as base)
Add Me, Et, R, and tBu labels
to match the first structure
b. Compare and contrast the examples on this page with the ones in Worksheet M, Question 2:
i. Each stereoisomer of bromoalkane leads to
E2 examples on this page.
Each stereoisomer of bromoalkane leads to
El examples on worksheet E, question 2.
Comment on other similarities/differences you notice between the two different worksheet
examples:
_(how many) stereoisomer(s) of product in the
ii.
_(how many) stereoisomer(s) of product in the
iii.
Transcribed Image Text:1. Orbitals and stereochemistry in the E2 reaction a. Add the orbitals and missing substituent labels to the starting material drawings below, showing orbital shading on the reactants that corresponds to the new bonds being formed (show only o* shading, although o is reacting too), then translate the alkene product perspective drawings into the corresponding flat alkene drawings. н-он OH nb O(sp3) R Br Me H. E2 tBu o*CH Et o*CBr Br flat drawing of alkene product Br add orbitals for the Add Me, Et, R, and tBu labels to match the first structure alkene product pi bond Add Me, Et, R, and tBu labels to match the first structure add orbitals for E2 reaction (hydroxide as base) H-OH OH nb O(sp3) R Br Me H. tBu' E2 O*CH Et o*CBr Br flat drawing of alkene product Br Add Me, Et, R, and tBu labels to match the first structure add orbitals for the alkene product pi bond add orbitals for E2 reaction (hydroxide as base) Add Me, Et, R, and tBu labels to match the first structure b. Compare and contrast the examples on this page with the ones in Worksheet M, Question 2: i. Each stereoisomer of bromoalkane leads to E2 examples on this page. Each stereoisomer of bromoalkane leads to El examples on worksheet E, question 2. Comment on other similarities/differences you notice between the two different worksheet examples: _(how many) stereoisomer(s) of product in the ii. _(how many) stereoisomer(s) of product in the iii.
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