Resistant to Base!

An organic chemistry-themed music video parodying Robert Palmer’s 1985 “Addicted to Love.“ Shot on Canon XL-1s (MiniDV) w/ Canon XL IS II 16X lens. Edited on Sony Vegas HD 6. ***LYRICS*** Your lights are on, but you’re not home You’re in the lab, working alone. Your synthesis is nearly done Just add a chain to that carbon. You can’t wait to alkylate But first you must deprotonate You add a mole of LDA To overcome that pKa Whoa, you like to think it will react with the stuff, oh yeah It’s closer to the truth to say you can’t add enough You know you’re gonna have to face it, it’s resistant to base. You check pH, it’s past fourteen Your stirring bar is dissolving The TLC shows no products Another mole and then reflux! With LDA, it won’t react Butyllithium just might abstract That hydrogen that won’t obey Le Chatelier’s communiqué Whoa, you like to think it will react with the stuff, oh yeah It’s closer to the truth to say you can’t add enough You know you’re gonna have to face it, it’s resistant to base. REFRAIN Might as well face it, it’s resistant to base. (x5) Your potassium t-butoxide And ammonium hydroxide Your KOH and hydrazine Push the pH beyond eighteen REFRAIN