P8.5: Predict the organic products of the following nucleophilic substitution reactions, all of which are carried out in polar aprotic solvent. Show stereochemistry at chiral carbons. Hints:

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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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P8.5: Predict the organic products of the following nucleophilic substitution reactions, all of
which are carried out in polar aprotic solvent. Show stereochemistry at chiral carbons. Hints:
Na2CO3, sodium carbonate, is a weak base. For part (f): What is the conjugate acid of NH
? What is the pKa of this conjugate acid, and what is the pK, of a terminal alkyne?
a.
NaⓇ
OTS
b.
C.
N
H
Na₂CO2
+
CH31
-ОН
d.
H3C Z
Br
NaH
CH3SNa
OTS
e.
H3C
N
Br., H
Na₂CO2
N
f.
H3C-C=C-H
Br
NaNH2
Transcribed Image Text:P8.5: Predict the organic products of the following nucleophilic substitution reactions, all of which are carried out in polar aprotic solvent. Show stereochemistry at chiral carbons. Hints: Na2CO3, sodium carbonate, is a weak base. For part (f): What is the conjugate acid of NH ? What is the pKa of this conjugate acid, and what is the pK, of a terminal alkyne? a. NaⓇ OTS b. C. N H Na₂CO2 + CH31 -ОН d. H3C Z Br NaH CH3SNa OTS e. H3C N Br., H Na₂CO2 N f. H3C-C=C-H Br NaNH2
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