Which product would be obtained if 3-methyl-2-butanol was used as the alcohol in the Electrophilic Aromatic Substitution: Friedel-Crafts Alkylation? Show the structure of the product. Explain briefly. Original reaction and more info is attached:

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter13: Substitution
Section: Chapter Questions
Problem 4E
icon
Related questions
icon
Concept explainers
Question

Which product would be obtained if 3-methyl-2-butanol was used as the alcohol in the Electrophilic Aromatic Substitution: Friedel-Crafts Alkylation? Show the structure of the product. Explain briefly.

Original reaction and more info is attached:

 

In this experiment, the tert.-butyl cation is produced by the reaction of tert. butanol and
concentrated sulfuric acid. A tert.-butyl cation will be used and since no carbocation rearrangement
can occur, any method can be used to produce this cation. Just remember that while anhydrous
AlCl3 is often used for Friedel-Craft reactions, this class of EAS simply requires a carbocation,
regardless of how it is generated.
In the current experiment, a different electrophile (the tert.-butyl cation) is used to alkylate
1,4-dimethoxybenzene. This is a Friedel-Crafts Alkylation reaction.
LOCH3
(H;C);C.
LOCH3
(CH3);COH
CH;COOH/H,SO4
H3CO
H3CO
`C(CH3)3
The primary difference between Friedel-Crafts EAS reactions and other EAS reactions
(i.e., nitration, halogenation, etc.) is that in a Friedel-Crafts reaction (alkylation or acylation), the
electrophile is a carbon atom (i.e., in this experiment it is a tert.-butyl carbocation). In many cases,
the Friedel-Crafts electrophile is generated using a chlorine-containing molecule (i.e., an acyl
[acid] chloride or an alkyl chloride) and an appropriate Lewis acid (i.e., AIC13, BF3) catalyst
Transcribed Image Text:In this experiment, the tert.-butyl cation is produced by the reaction of tert. butanol and concentrated sulfuric acid. A tert.-butyl cation will be used and since no carbocation rearrangement can occur, any method can be used to produce this cation. Just remember that while anhydrous AlCl3 is often used for Friedel-Craft reactions, this class of EAS simply requires a carbocation, regardless of how it is generated. In the current experiment, a different electrophile (the tert.-butyl cation) is used to alkylate 1,4-dimethoxybenzene. This is a Friedel-Crafts Alkylation reaction. LOCH3 (H;C);C. LOCH3 (CH3);COH CH;COOH/H,SO4 H3CO H3CO `C(CH3)3 The primary difference between Friedel-Crafts EAS reactions and other EAS reactions (i.e., nitration, halogenation, etc.) is that in a Friedel-Crafts reaction (alkylation or acylation), the electrophile is a carbon atom (i.e., in this experiment it is a tert.-butyl carbocation). In many cases, the Friedel-Crafts electrophile is generated using a chlorine-containing molecule (i.e., an acyl [acid] chloride or an alkyl chloride) and an appropriate Lewis acid (i.e., AIC13, BF3) catalyst
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 3 steps with 2 images

Blurred answer
Knowledge Booster
Ethers
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: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:
9780618974122
Author:
Andrei Straumanis
Publisher:
Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC L
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:
9781305446021
Author:
Lampman
Publisher:
CENGAGE LEARNING - CONSIGNMENT
Macroscale and Microscale Organic Experiments
Macroscale and Microscale Organic Experiments
Chemistry
ISBN:
9781305577190
Author:
Kenneth L. Williamson, Katherine M. Masters
Publisher:
Brooks Cole