?Predict the product of the reaction of propanal with each of the following:(a) Lithium

Chapter 18, Problem 18.27

(choose chapter or problem)

Predict the product of the reaction of propanal with each of the following:

(a) Lithium aluminum hydride, followed by water

(b) Sodium borohydride, methanol

(c) Hydrogen (nickel catalyst)

(d) Methylmagnesium iodide, followed by dilute acid

(e) Sodium acetylide, followed by dilute acid

(f) Phenyllithium, followed by dilute acid

(g) Methanol containing dissolved hydrogen chloride

(h) Ethylene glycol, p-toluenesulfonic acid, benzene

(i) Aniline (C6H5NH2)

( j) Dimethylamine, p-toluenesulfonic acid, benzene

(k) Hydroxylamine

(l) Hydrazine

(m) Product of part (l) heated in triethylene glycol with sodium hydroxide

(n) p-Nitrophenylhydrazine

(o) Semicarbazide

(p) Ethylidenetriphenylphosphorane \(\left[\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{3} \stackrel{+}{\mathrm{P}}-\overline{\ddot{\mathrm{C}}} \mathrm{HCH}_{3}\right]\)

(q) Sodium cyanide with addition of sulfuric acid

(r) Chromic acid

Text Transcription:

[(C_6H_5)_3 stackrel +P - overline ddot CHCH_3]