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18. (2 pts.) The equations for organic reactions usually focus on the desired transformation from reactant to product, other possible products such as byproducts and/or side products are often not included, even though it is understood that these are also formed in almost every organic reaction. Shown below is a complete equation for the ester synthesis reaction for the case of 2-pentanol, that includes all possible products, including the desired product, side product(s) and in this case some byproducts (s). Assign each of the four provides products as a desired, side product or a byproduct o: H2SO4 cat. H H. Нас heat Н,с HEORH 19. (2 pts.) The boiling point of hexanol is around 155 °C and that for hexane is around 68'C. This is clearly due to strong hydrogen bonding in hexanol (indicated below) that must be overcome in order to separate the molecules in the liquid phase. In the structures below, clearly indicate which are the covalent O-H bond(s) and which are the O-H hydrogen bond(s). H hexane 68 °C hexanol 155 °C 20. (3 pts.) Using your infrared spectrum of the pure ester product, complete the table below for all peaks with frequencies greater than 1500 cm that can be assigned to vibrations of specific bonds. For each peak give the frequency, the specific bond that vibration frequency refers to and where appropriate the functional group that bond is part of specific bond vibration functional pure ester Peak % pure ester Peak cm group

Answer 1

Question 18.

(i) Ester (Pentan-2-yl acetate) is the desired product.

(ii) Ketone (2-Pentanone) and alkene (2-pentene) are the side-products.

(iii) water (H₂O) is the by-product.

Question 19.

detted Lime: o-H hydynbond NAmal Line o-H covalet nd -Hhydrogen bond Calent -H 6anda