CHAIN REACTION
Based on, er, "Chain Reaction" by Diana Ross
Original Words and Music by the Bee Gees

(Pay attention, this one's quite hard to follow)

 

BROMINE RADICAL TO PROPENE
Sp2 hybridised and double-bonded -
You’ve got electron density, I want it!
I had my hydrogen nicked - I’m unstable -
(It’s what peroxides do
Best)

PROPENE TO BROMINE RADICAL
You’re dodgy with your hydrogen fallen off -
Reactive, ‘cos of your unpaired electron,
You need to break my pi-system, bond with me! -
A spare electron:
I’ll be just like you;

PEROXIDE RADICAL TO HBr                             HBr
I’m the beginning of a chain reaction -              (Chain reaction!)
I start it off with hydrogen abstraction;                (Abstract my H - )
I need to stick you where I can nick your H -            (Unpaired electron…)   
I’ll be stable then;

  PEROXIDE RADICAL TO PROPENE                    PROPENE                 
I’ve undergone a homolytic fission -                  (…lytic fission!)
I’ve started off free radical addition! We                    (Break my pi-bond - )
Need you to have an unpaired e too                    (I’ll be unstable…)
So it can start again -

ALL
To form more radical-al-als, to form more radicals;
To form more radical-al-als, to form more radicals.

  PROPENE                                                            PEROXIDE RADICAL     
We’ll swap electrons round in propagation -                   (Oooh, electrons…)
One day we might just get to termination:                      (Oooh, electrons…)
The mechanism’s regi-oselective,
Unexpected, too -
‘Cos

HBr
The final product’s anti-Markovnikov:
To carbon with the most H, bromine adds on,
You’ll always get 1-bromopropane with me
With peroxides:
All we’ve got to do is -

(PEROXIDE RADICAL abstracts HBr’s hydrogen; resulting BROMINE RADICAL attacks PROPENE)

BROMOPROPANE RADICAL  (As it now is)             PEROXIDE RADICAL/PEROXIDE
Get in the middle of a chain reaction!                             (A chain reaction!)
It’s just repeated electron transaction;                         (I’m homolysed!)
You need to homolyse those weak single bonds - it’s          (Unpaired electron…)
Initiation (uv radiation!)
You get free radical regeneration                            (Regeneration!)
(They’re like a catalyst) in propagation, they                (Oooh, break my bond…)
Need to pair that electron that’s spare,                       (I’ll be unstable…)
With whatever’s in their way -

ALL
They form more radical-al-als, they form more radicals.

PEROXIDE RADICAL
You get free radical regeneration - need to pair that electron -
All you’ve got to do -

BROMOPROPANE RADICAL                           PEROXIDE RADICAL/PEROXIDE        
Get in the middle of a chain reaction                                         A chain reaction!
It’s just repeated electron transaction                                       I’m homolysed!
You need to homolyse those weak single bonds -                       I’ll be unstable…
Initiation -
uv radiation!                                                                      uv radiation!  
You get free radical regeneration                                         Regeneration!  
(They’re like a catalyst) in propagation                              Ooooh, break my bond…
Need to pair that electron that’s spare, with                     Unpaired electron…

ALL
Whatever’s in their way,   
                                                                                         All you’ve got to do is…

BROMOPROPANE RADICAL
Get in the middle of a chain reaction…   A chain reaction…


©
Aimee Hartnell, September 2001