The Influence of Branched Chains on Optical Activity. The Configuration of Propyl-t-butylcarbinol, with a Note on the Relation between Rotatory Power and Chemical Character

Abstract

The solid first dissolved, this was followed by the appearance of yellow colored needles. After cooling, the solution deposited a curdy yellow precipitate. The solid was recrystallized from ethyl acetate and melted at 209°; yield 0.12 g.

Rearrangement in Alkyl Groups during Substitution Reactions

“…Some secondary, and possibly primary chlorides, may also be been made between the effect on rotatory power of branched alkyl groups in various carbinols and their propensity to rearrangement in reactions with hydrogen chloride. At 25°the following percentage rearrangements to tertiary halides were observed (possible rearrangement to other secondary structures not being accounted for) (171). Optically active D-2,2-dimethylhexan-3-ol gave, with hydrogen chloride, a mixture of two inactive tertiary halides and a smaller amount of the unrearranged nsecondary chloride (170).…”