explanation that is easy to follow

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter17: Alcohols And Phenols
Section17.SE: Something Extra
Problem 54AP: The 1HNMR spectrum shown is that of 3-methyl-3-buten-1-ol. Assign all the observed resonance peaks...
icon
Related questions
icon
Concept explainers
Question

Please include steps and an explanation that is easy to follow

Rosalind carried out the reaction below in the lab, with a slight excess of methyl iodide.
She expected to obtain a pristine ¹H NMR spectrum given her usual success in the lab!
She noticed however that in addition to the expected peaks, there were unexpected
peaks in the alkyl and aromatic regions. In the aromatic region, one additional signal
with no splitting was observed and in the alkyl region, one additional signal with no
splitting was also observed.
CH3CI
AICI 3
CH3
a. How many unique signals were expected in the ¹H NMR of Cameron's expected
product?
b. Draw a side product that is consistent with the additional signals observed by
Rosalind.
c. Using your knowledge of electrophilic aromatic substitutions, explain why a
noticeable amount of this side product formed, and why it can be difficult to avoid!
Transcribed Image Text:Rosalind carried out the reaction below in the lab, with a slight excess of methyl iodide. She expected to obtain a pristine ¹H NMR spectrum given her usual success in the lab! She noticed however that in addition to the expected peaks, there were unexpected peaks in the alkyl and aromatic regions. In the aromatic region, one additional signal with no splitting was observed and in the alkyl region, one additional signal with no splitting was also observed. CH3CI AICI 3 CH3 a. How many unique signals were expected in the ¹H NMR of Cameron's expected product? b. Draw a side product that is consistent with the additional signals observed by Rosalind. c. Using your knowledge of electrophilic aromatic substitutions, explain why a noticeable amount of this side product formed, and why it can be difficult to avoid!
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 2 images

Blurred answer
Knowledge Booster
Electronic Effects
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305080485
Author:
John E. McMurry
Publisher:
Cengage Learning