Sigma and Pi Bonds

Chemistry Level 1

2,2,5,5-tetramethyl-3-hexene 2,2,5,5-tetramethyl-3-hexene

Which bond would you expect to break first in this molecule?

Sigma bond in C-H single bond Pi bond in C-C double bond Sigma bond in C-C double bond

Jordan Calmes by Jordan Calmes , 33, USA

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6 solutions

Soham Sen
Dec 14, 2017

The Carbon-Carbon double bond is made of 1 sigma and 1 pi bond (because, double bond includes a pi bond). Sigma bonds are strongest. So, pi bonds will break first. Other bonds are only 1 sigma, whereas the Carbon-Carbon double bond is is 1 sigma + 1 pi. This makes it the strongest. In this, the pi bond will break first.

15 Helpful 1 Interesting 0 Brilliant 0 Confused
Jordan Calmes
Apr 18, 2016

Relevant wiki: Sigma and Pi Bonds

The carbon-carbon and carbon-hydrogen bonds are sigma bonds, while the carbon-carbon double bond includes a pi bond.

10 Helpful 0 Interesting 0 Brilliant 1 Confused

I selected the: Pi bond in C-C double bond and it said it was incorrect?

A Former Brilliant Member - 2 years ago
Dulce Soto
Nov 21, 2018

Pi bonds are weaker than sigma bonds. Therefore, Pi bonds will break before a sigma bond.

3 Helpful 1 Interesting 0 Brilliant 0 Confused
Brad Muya
Apr 22, 2019

Pi bonds are the weakest type of bond, there exists one pi bond between the Carbon-Carbon, double bond. Since this is the only Pi bond and knowing pi bonds are weaker than sigma bonds, this has the highest chance of breaking compared to the other sigma bonds.

1 Helpful 0 Interesting 0 Brilliant 0 Confused

So is the answer: "Pi bond in C-C double bond"? Because I selected this and it said it was incorrect.

A Former Brilliant Member - 2 years ago
Gafanhoto Rosa
Nov 27, 2020

Pi bonds are weaker than sigma bonds.

0 Helpful 0 Interesting 0 Brilliant 0 Confused
Hana Aria
Jan 19, 2020

Sigma bonds are stronger than pi bonds. Sigma ponds are low in energy.

0 Helpful 0 Interesting 0 Brilliant 0 Confused

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