Choose the best explanation for the proposed curved arrow mechanism for SN2 shown below. H : Br CH3 H H. :Br: .! 0 :S: CH3 :S: CH3 CH3 The strong polarity of the carbon-bromine bond A dipole attracts the negative sulfur; the sulfur repels the bromine atom and causes it to leave. B The partially positive carbon is attracted to the negatively charged sulfur, forming a carbon-sulfur bond. The bromide is forced to leave to avoid making an octet rule violation. The strongly electronegative bromine attracts the negatively charged sulfur ion. The sulfur's negative C charge is transferred to the bromine and the sulfur and carbon bond to each other to complete the octet on each atom. The strong polarity of the carbon-bromine bond dipole results in a partially positive carbon electrophile. The sulfur's negative charge is attracted to the electrophilic carbon of the C-Br bond. The electrons donated from the nucleophile become the new σ bond while displacing the C-Br bond breaks.
Choose the best explanation for the proposed curved arrow mechanism for SN2 shown below. H : Br CH3 H H. :Br: .! 0 :S: CH3 :S: CH3 CH3 The strong polarity of the carbon-bromine bond A dipole attracts the negative sulfur; the sulfur repels the bromine atom and causes it to leave. B The partially positive carbon is attracted to the negatively charged sulfur, forming a carbon-sulfur bond. The bromide is forced to leave to avoid making an octet rule violation. The strongly electronegative bromine attracts the negatively charged sulfur ion. The sulfur's negative C charge is transferred to the bromine and the sulfur and carbon bond to each other to complete the octet on each atom. The strong polarity of the carbon-bromine bond dipole results in a partially positive carbon electrophile. The sulfur's negative charge is attracted to the electrophilic carbon of the C-Br bond. The electrons donated from the nucleophile become the new σ bond while displacing the C-Br bond breaks.
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter12: Chirality
Section: Chapter Questions
Problem 25CTQ
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Transcribed Image Text:Choose the best explanation for the proposed curved arrow mechanism for SN2
shown below.
H
: Br
CH3
H
H.
:Br:
.! 0
:S:
CH3
:S:
CH3
CH3
The strong polarity of the carbon-bromine bond
A dipole attracts the negative sulfur; the sulfur repels
the bromine atom and causes it to leave.
B
The partially positive carbon is attracted to the
negatively charged sulfur, forming a carbon-sulfur
bond. The bromide is forced to leave to avoid
making an octet rule violation.
The strongly electronegative bromine attracts the
negatively charged sulfur ion. The sulfur's negative
C charge is transferred to the bromine and the sulfur
and carbon bond to each other to complete the octet
on each atom.
The strong polarity of the carbon-bromine bond
dipole results in a partially positive carbon
electrophile. The sulfur's negative charge is attracted
to the electrophilic carbon of the C-Br bond. The
electrons donated from the nucleophile become the
new σ bond while displacing the C-Br bond breaks.
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