MCAT Organic Chemistry Review 2018-2019

(singke) #1

Let’s go through the steps again.


Therefore, the primary product of this reaction will be ethanoic acid.


Reaction 3


Determine the product of a reaction between 2-amino-3-hydroxypropanoic acid and 2,6-
diaminohexanoic acid in aqueous solution.


Let’s go through the steps one last time.


First,  let’s   draw    out our molecules.

This    molecule    has an  alkane  backbone    and a   primary alcohol.    Alcohols    make    good
nucleophiles and can also be oxidized. The hydroxyl group can also act as a leaving group,
especially if it gets protonated.

Next,   the reagents.   Dichromate  is  a   good    oxidizing   agent.

The alcohol carbon  is  most    likely  to  react   because it  is  the most    oxidized.

The primary product of  a   primary alcohol with    a   strong  oxidant like    dichromate  will    be  a
carboxylic acid. One other possible product could have been an aldehyde, so this could trip us up!
Remember, however, that primary alcohols can only be oxidized to aldehydes by reagents
specifically designated for this purpose, like pyridinium chlorochromate (PCC). If we start with
ethanol, we’ll obtain ethanoic acid (acetic acid) after reaction with dichromate.

Stereospecificity   again   isn’t   a   consideration   and won’t   change  the outcome in  this    reaction.

First,  let’s   draw    out both    molecules.
Free download pdf