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Furfuryl chloride can undergo substitution by both SN2 and

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 68SP Chapter 6

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 68SP

Furfuryl chloride can undergo substitution by both SN2 and SN1 mechanisms. Since it is a 1° alkyl halide, we expect SN2 but not SN1 reactions. Draw a mechanism for the SN1 reaction shown below, with careful attention to the structure of the intermediate. How can this primary halide undergo SN1 reactions? Why is there no competition with E2 or E1 mechanisms?

Step-by-Step Solution:

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.

Step 2:

Furfuryl chloride which is a primary alkyl halide has lone pair of electrons on the oxygen atom, which participates in the formation of bond when nucleophile attacks it and hence it undergoes SN1 reaction. This mechanism is explained below.

Step 3:

The mechanism for the given SN1 reaction is shown below :

         The C-Cl bond in the furfuryl chloride compound undergoes dissociation and the furanium ion is formed as product. This ion is cation and is stabilized by resonance as shown above. The formate ion of the sodium formate compound acts as nucleophile and attacks the substrate(substrate is the compound that is being attacked by the nucleophile. Hence, here furfuryl chloride is the substrate ). This nucleophilic attack is shown in the next step

Step 4 of 5

Chapter 6, Problem 68SP is Solved
Step 5 of 5

Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8. Organic Chemistry was written by and is associated to the ISBN: 9780321768414. The full step-by-step solution to problem: 68SP from chapter: 6 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM. Since the solution to 68SP from 6 chapter was answered, more than 1086 students have viewed the full step-by-step answer. This full solution covers the following key subjects: undergo, reactions, mechanisms, halide, Intermediate. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. The answer to “Furfuryl chloride can undergo substitution by both SN2 and SN1 mechanisms. Since it is a 1° alkyl halide, we expect SN2 but not SN1 reactions. Draw a mechanism for the SN1 reaction shown below, with careful attention to the structure of the intermediate. How can this primary halide undergo SN1 reactions? Why is there no competition with E2 or E1 mechanisms?” is broken down into a number of easy to follow steps, and 61 words.

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