Can someone explain the slide please, what does it mean Polyalkylation is often oberved?? only disubstituted product can be major product ? can trisubsituted also exist in this reaction? I am confused .

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter9: Alkynes: An Introduction To Organic Synthesis
Section9.SE: Something Extra
Problem 46AP: A hydrocarbon of unknown structure has the formula C8H10. On catalytic hydrogenation over the...
icon
Related questions
Question

Can someone explain the slide please, what does it mean Polyalkylation is often oberved??  only disubstituted product can be major product ? can trisubsituted also exist in this reaction? I am confused .

12
Chapter 16.
FRIE DEL
3. It is often
substitution.
RA
ALCE
4. Skeletal
a
sometimes
primary
CH₂ CH₂ CH₂ CL
AlCl3
CH3 CH CH₂
GH 3
сна-лесна с
CH 3
Ala 3
EAS
CRAFTS ALKYLATION
4
LIMITS
difficult to stop alkylation after a single
Polyalkylation is often observed.
R
R
L
+
rearrangement of the alkyl carbocation electrophile
occurs during reaction, especially when
(10) alkyl halide
(10) alkyl halide is used.
CH3
CH-CH3
CH₂ CH₂ CH₂
minor
major
11
monosubstituted
product
+
hydride
shift Снзен сна
CH 3
•C-CH₂
+
1
CH₂ CH3
R major
disubstituted
product
minor
CH3
alkyl
+
CH ₂ -C- CH₂ + shift > CH₂-C-CH₂CH₂
CH3
1
CH3
3
Transcribed Image Text:12 Chapter 16. FRIE DEL 3. It is often substitution. RA ALCE 4. Skeletal a sometimes primary CH₂ CH₂ CH₂ CL AlCl3 CH3 CH CH₂ GH 3 сна-лесна с CH 3 Ala 3 EAS CRAFTS ALKYLATION 4 LIMITS difficult to stop alkylation after a single Polyalkylation is often observed. R R L + rearrangement of the alkyl carbocation electrophile occurs during reaction, especially when (10) alkyl halide (10) alkyl halide is used. CH3 CH-CH3 CH₂ CH₂ CH₂ minor major 11 monosubstituted product + hydride shift Снзен сна CH 3 •C-CH₂ + 1 CH₂ CH3 R major disubstituted product minor CH3 alkyl + CH ₂ -C- CH₂ + shift > CH₂-C-CH₂CH₂ CH3 1 CH3 3
Expert Solution
steps

Step by step

Solved in 2 steps with 2 images

Blurred answer
Knowledge Booster
Designing a Synthesis
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
Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:
9780618974122
Author:
Andrei Straumanis
Publisher:
Cengage Learning