16.Oh Grignard, the Beautiful
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(Sung to the tune of America the Beautiful)
The carbonyl is polarized;
The carbon end is plus.
A nucleophile will thus attack
The carbon nucleus.
A Grignard yields an alcohol
Of types there are but three.
It forms a bond to correspond
From C to shining C.
A secondary's synthesis
Requires an aldehyde.
For tertiary, a carbanion
And ketone may collide.
And Grignards add formaldehyde
The product's primary
They stick like glue to CO2
Join C to lonely C.
*Author unknown* Collected by Dr.Slime 1997
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17. Glory, Glory, It's Wolff-Kischner
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(to the tune of "The Battle Hymn of the Republic")
Take a ketone carbonyl and then react with hydrazine.
It forms a hydrazone, of course, and water leaves the scene.
An NH from the NH2, hydroxide will attack.
Resonance occurs and then the carbon grabs H back.
------
Glory, Glory, It's Wolff-Kischner!
Glory, Glory, It's Wolff-Kischner!
Glory, Glory, It's Wolff-Kischner!
Reduce the carbonyl and then the side-chain now is plain.
------
Hydroxide base is still present, it steals the last H plus.
Now add a little heat, the N2 leaves without a fuss.
The carbon gets a hydrogen producing an alkane.
Now the carbon chain is plain.
------
Glory, Glory, It's Wolff-Kischner!
Glory, Glory, It's Wolff-Kischner!
Glory, Glory, It's Wolff-Kischner!
Reduce the carbonyl and then the side-chain now is plain.
------
by Kristy Bruno, Val Stetts, Tracy Albrecht 6 May 1996 edited by Professor Casteel from Bucknell University, Lewisberg, Pa.
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18. Oh, My Ketone!
------
(Sung to the tune of "Oh, My Darling Clementine")
------
Oh, my ketone! Oh, my ketone!
And my primary amine.
You reacted, lost some water and
You formed a new imine.
------
Now the lone pair on the N then
Bonds with carbonyl C.
Pi electrons go to O, a
Proton shifts fast as can be.
------
Now the O is feeling greedy
Grabs an H from OH3.
Free electrons from the N then
Form a pi bond, water leaves.
------
Now the N is protonated
And a plus charge can be seen.
So the water yanks the H off
And we've formed a new imine.
------
Oh, my ketone! Oh, my ketone!
And my primary amine.
You reacted, lost some water and
You formed a new imine.
------
by William Evans 6 May 1997.Source: BucknellUniversity, Lewisberg, Pa.
19. The Aldol Reaction
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(Sung to the tune of the Hokey-Pokey)
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You put a strong base in,
It takes the alpha-H out:
This forms an enolate.
That's what this carbonyl's about.
The enolate will resonate,
The charge is shared by O.
That's what aldol's about.
------
The enolate attacks
Another carbonyl about.
A new bonds forms;
It's really neat without a doubt.
A beta-hydroxycarbonyl is the result.
That's what aldol's about.
------
by Patrick Costello and Graig Garrett, 6 May 1996 edited by Dee Casteel Source: BucknellUniversity, Lewisberg, Pa.
20. Oh, You Butadiene.
------
(Sung to the tune of Oh, You Beautiful Doll)
Oh, you butadiene, you great big butadiene
Times I love you, times I hate you
How, I'd love to brominate you
Oh, you butadiene, you great big butadiene
I would ozonize you, but I fear you'd break
If you polymerize, my heart will ache
Oh, oh, oh, oh, Oh you butadiene
(Your're double bonded) - < spoken with feeling>
Oh, you butadiene
(You're conjugated) - < spoken with feeling>
Oh, you butadiene
(Source: C. N. Peck Delta College Chemistry Dept. 1999)