Question

CHE351NMRQuiz3 Fall2019 CHE 351-03 Organic Chem I Fall 2019 NMR Quiz 3 Name t-Butylbenzene was reacted with 1-bromopropane in the presence of AlCl as a catalyst. AC The product was believed to be one of the following isomers. single product was isolated from the reaction mixture and the C-NMR spectrum of the compound was obtained. Which of the candidate product structures is most consistent with the spectrum? 140 120 80 PPM 160 40 100 60

Answer 1

+ na Alcz. t-butyl benzene Above reaction is an example for friedel coapt-alkylation reaction. from the given 13 C-NMR spectra it is confirms the formation of B. Because there are 8 peaks are present in the given spectrum Hence compound - haves 9 peats ®-gives & peaks © - gives 10 peaks - gives il pears Therefore sloucture B is correct answer. 0 Gehoo Double bond equivalence - 2172-H - 2x8+2-10-4 (DBE) DBE is 4 indicates three double bonds and one ring from the IR spectra it is clear that, -OH group is present in the given molecule. UV-ves spectrum : dmax -223 om indicate extented conjugation is absent .. from the above fact the structure can be derived as OH