Draw the major organic product of each reaction. Indicate the stereochemistry at the stereogenic center. Omit byprodu...

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Draw the major organic product of each reaction. Indicate the stereochemistry at the stereogenic center. Omit byprodu...

Draw the major organic product of each reaction. I

Draw the major organic product of each reaction. Indicate the stereochemistry at the stereogenic center. Omit byproducts such as salts. If applicable, expand octets to minimize formal charges.

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Answer 1

Answer #1

Concepts and reason

The concept is draw the major organic products, when chlorination of alcohol with thionyl chloride and TsCl, followed by nucleophilic attack of ${\rm{C}}{{\rm{H}}_3}{{\rm{S}}^ - }$ .

Fundamentals

Alcohols reacts with thionyl chloride ${\rm{(SOC}}{{\rm{l}}_{\rm{2}}})$ to form alkyl chloride. This reaction proceeds through ${\rm{S}}{{\rm{N}}_{\rm{2}}}$ mechanism.

Alcohols reacts with tosyl chloride ${\rm{(TsCl}})$ to form alkyl chloride. This reaction proceeds through ${\rm{S}}{{\rm{N}}_1}$ mechanism.

The reaction is,

CH3
SOCI2
Stereochemistry is
inverted.
Pyridine
HIS
Н.
OH
SN2
SN2 CH3S
CH3
Hindi)
SCH

The reaction is,

Tsci
Honnis
Hilmis
OH
Pyridine
SN
SN2
CH3S
CH3
SCH

Ans:

Thus, the major organic products are,

CH3
CH3
L
Hoy
llll
SOCl2
Pyridine
Tsci
Pyridine
ID OTS
CH3
CHzs
CH3S
Hill
OH
CH3
H111111
Olly
SCH;
SCH

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Answer 2

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