CH3 NA "OH Primary and secondary alcohols can be converted to alkyl chlorides via treatment with thionyl chloride. The reaction proceeds via an SN2 mechanism with inversion of configuration at the chiral carbon. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions XT CH3 SOCI₂ "OH CH3 CH3 * -oh :0: 'O. CI:

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Chapter22: Carbonyl Alpha-substitution Reactions
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Problem 26MP: Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium...
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#7). Second picture shows how to use arrows correctly. 

CH3
NA
'OH
CH3
Primary and secondary alcohols can be converted to alkyl chlorides via treatment with thionyl chloride. The reaction proceeds via an SN2 mechanism with inversion of configuration at the chiral carbon.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
X
SOCI₂
"OH
CH3
:O:
CH3
H
:O:
S
Transcribed Image Text:CH3 NA 'OH CH3 Primary and secondary alcohols can be converted to alkyl chlorides via treatment with thionyl chloride. The reaction proceeds via an SN2 mechanism with inversion of configuration at the chiral carbon. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions X SOCI₂ "OH CH3 :O: CH3 H :O: S
Specifying Hotspot End Position Instructions
Make the ends of your curved arrows specify the destination of the reorganizing electron(s) as exactly as
possible. Keep in mind that not all hotspots are interchangeable; for example, an arrow starting/ending at the
interior of an atom (represented by an atomic symbol) is not the same as an arrow starting/ending at a lone pair.
correct
H-ti:
incorrect
correct
H
H₂CC+
incorrect
H
CH3
H₂C-C+
CH3
CH3
CH3
-H*
-H*
H*
H*
H₂C=
H₂C=C
CH3
CH3
CH3
CH3
Transcribed Image Text:Specifying Hotspot End Position Instructions Make the ends of your curved arrows specify the destination of the reorganizing electron(s) as exactly as possible. Keep in mind that not all hotspots are interchangeable; for example, an arrow starting/ending at the interior of an atom (represented by an atomic symbol) is not the same as an arrow starting/ending at a lone pair. correct H-ti: incorrect correct H H₂CC+ incorrect H CH3 H₂C-C+ CH3 CH3 CH3 -H* -H* H* H* H₂C= H₂C=C CH3 CH3 CH3 CH3
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