Orgo question

[riro2]

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Dimethylpropylamine (N,N-dimethyl-1-propanamine) will be LEAST soluble in which of the following?

a) dilute KOH(aq)
b) dilute HCl(aq)
c) dimethyl ether
d) benzene
e) concentrated H2SO4

Answer is: dilute KOH

Can someone please explain this to me?

Thanks in advance

 

[Jia7]

Dimethylpropylamine (N,N-dimethyl-1-propanamine) will be LEAST soluble in which of the following?

a) dilute KOH(aq)
b) dilute HCl(aq)
c) dimethyl ether
d) benzene
e) concentrated H2SO4

Answer is: dilute KOH

Can someone please explain this to me?

Thanks in advance

Hey dimethylpropanamine is non polar. From the answer choices KOH is the most polar molecule and thus will not dissolve the non polar solute well.

 

[CANgnome]

the species is nonpolar.

so you want a polar solution.

if you add acid, it protonates dimethypropylamine, making it charged, allowing it to dissolve.

what you want is a polar solution that will not protonate, KOH (aq)