Question

We performed a synthesis of methyl diantilis lab. The first step involved a Sodium Borohydride Reduction of 3-Ethoxy-4-hydroxybenzaldehyde (Ethylvanillin) shown below.

он OR NaBH4 ROH NaOH Amberlyst-15 он он он Ethylvanilin R- CH3 (Methyl Diantilis) CH2CH3 CH(CH3)2 CH2CH2CH3

The next step of the experiment involved Etherification of 3-ethoxy-4-hydroxylbenzyl Alcohol using one of four alcohols (methanol, ethanol, 1-propanol, or 2-propanol). The alcohol I used was methanol. The reaction is predicted below.

Below is the NMR sample for my product with the integration and ppm for each peak displayed.  

Based on this information, answer the following questions.

a. Check to see if my predicted reaction and product is accurate. Please draw one yourself so I can compare.

b. Label each peak on the NMR spectrum as best as possible. (note: when I attempted to do this, I was confused as I counted 16 hydrogens. however, my nmr data seems to display less)

c. If the NMR spectrum is missing peaks, please note where those missing peaks should belong.

d. If there are impurities, please identify where and what impurity (water, diethyl ether, etc). Calculate the molar ratio of each impurity to the desired product.

e. Please explain any errors with my NMR and what experimental errors may have caused this.

Answer 1