quaternary amines chiral/light polarizing?

[thebillsfan]

---

Members do not see this ad.

are quaternary amines chiral? can they rotate plane of polarized light? what about a tertiary amine with a lone pair? i'd say no to the tertiary amine because it can undergo pyramidal inversion, but just thought id check

 

[loveoforganic]

Exactly right

 

[Hemichordate]

I also heard that NH4+ is a good leaving group. Is that true? If so, does the + charge affect its leaving group ability? (I have only seen about neutral and negatively charged leaving groups before)

 

[thebillsfan]

I also heard that NH4+ is a good leaving group. Is that true? If so, does the + charge affect its leaving group ability? (I have only seen about neutral and negatively charged leaving groups before)

i believe that is true. for example, tertiary amines cannot form an amide, because when the lone pair attacks the carbonyl carbon to form a quaternary amine, it gets kicked right back off.

 

[loveoforganic]

I also heard that NH4+ is a good leaving group. Is that true? If so, does the + charge affect its leaving group ability? (I have only seen about neutral and negatively charged leaving groups before)

It's impossible to have NH4+ as a leaving group, given that nitrogen can only form 4 bonds. NR4+ on the other hand, is a good leaving group - hoffman elimination.