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Furfuryl chloride can undergo substitution by both SN2 and
Chapter 8, Problem 68SP(choose chapter or problem)
Furfuryl chloride can undergo substitution by both \(S_{N} 2 \text { and } S_{N} 1\) mechanisms. Since it is a \(1^{\circ}\) alkyl halide, we expect \(S_{N} 2\) but not \(S_{N} 1\) reactions. Draw a mechanism for the \(S_{N} 1\) reaction shown below, with careful attention to the structure of the intermediate. How can this primary halide undergo \(S_{N} 1\) reactions? Why is there no competition with \(E 2 \text { or } E 1\) mechanisms?
Equation Transcription:
Text Transcription:
SN2 and SN1
1°
SN2
SN1
SN1
SN1
E2 or E1
NaOCHO
NaCl
Questions & Answers
QUESTION:
Furfuryl chloride can undergo substitution by both \(S_{N} 2 \text { and } S_{N} 1\) mechanisms. Since it is a \(1^{\circ}\) alkyl halide, we expect \(S_{N} 2\) but not \(S_{N} 1\) reactions. Draw a mechanism for the \(S_{N} 1\) reaction shown below, with careful attention to the structure of the intermediate. How can this primary halide undergo \(S_{N} 1\) reactions? Why is there no competition with \(E 2 \text { or } E 1\) mechanisms?
Equation Transcription:
Text Transcription:
SN2 and SN1
1°
SN2
SN1
SN1
SN1
E2 or E1
NaOCHO
NaCl
ANSWER:
Solution 68SP :
Step 1:
Here, we have to draw a mechanism for the SN1 reaction shown below, and state how can this primary halide undergo SN1 reactions. And also mention why is there no competition with E2 or E1 mechanisms.
Primary halides usually undergo SN2 reactions as they have less steric hindrance(it is prevention of chemical reaction by large groups present in a molecule) to the nucleophilic attack and also they are less stable.