QUESTIONS 1. Two students were asked to obtain IR and NMR spectra before and after their experiment. One started with 2-chlorobenzaldehyde, the other started with 4chlorobenzaldehyde. They both obtained the corresponding carboxylic acids. They took their spectra together and forgot to label them and mixed them all up. a. Can 2-chlorobenzaldehyde and 4-chlorobenzaldehyde be differentiated using IR? b. Can 2-chlorobenzoic acid and 4-chlorobenzoic acid be differentiated using IR? c. How about differentiating 2-chlorobenzaldehyde and 2-chlorobenzoic acid using IR ? d. Can you differentiate the compounds using NMR? How many 1H NMR signals would you expect for: i. 2-chlorobenzaldehyde ii. 2-chlorobenzoic acid iii. 4-chlorobenzaldehyde iv. 4-chlorobenzoic acid