Three Organic Name Reaction Songs



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.

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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.

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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.

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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.

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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!

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(Sung to the tune of "Oh, My Darling Clementine")

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Oh, my ketone! Oh, my ketone!

And my primary amine.

You reacted, lost some water and

You formed a new imine.

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Now the lone pair on the N then

Bonds with carbonyl C.

Pi electrons go to O, a

Proton shifts fast as can be.

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Now the O is feeling greedy

Grabs an H from OH3.

Free electrons from the N then

Form a pi bond, water leaves.

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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.

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Oh, my ketone! Oh, my ketone!

And my primary amine.

You reacted, lost some water and

You formed a new imine.

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by William Evans 6 May 1997.Source: Bucknell University, 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.

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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.

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by Patrick Costello and Graig Garrett, 6 May 1996 edited by Dee Casteel Source: Bucknell University, Lewisberg, Pa.

20. Oh, You Butadiene.

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(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)

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