Question

Consider the Wednesday July 29 Breakout Problem 2. Outline briefly the synthesis of DEET including the synthesis of both the amine and the aromatic ring. Comment on how (if at all) the presence of the nitrogen will show up in spectroscopy (IR, Mass Spec and NMR)

Answer 1

Synthesis -OH Ansi- CH3 KMnO4 Coxidation) toluene CH₂-C1 (Bengene) Anny Allaz [Freidal-Chaft's alkylation benzoic acid J CH₂U Anky Adela 10 CH₂ -OH Lug 4 0 (_d NH -4 Base [NaoH) - (N,N-diethyl meta-toluamide)

¹HNMR spectra

7.59 7.58 7.58 7.46 7.46 7.45 7.45 -7.45 7.44 7.38 -7.37 7.37 7.36 7.35 -7.34 3.74 -3.73 3.71 3.70 -2.42 1.25 1.23 -1.21 094 9 нс . ** B (m) 745 A (m) 7.58 F(t) 3.72 2.42 1323 c(m) 7.36 11 12 W 4.00-1 2.95- 601-1 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 5.0 4.5 f1 (ppm)

Īn the IR spectra peak for C-N bond would appear in the range 1080-1360 cm^-1

^{For mass, peak for following fragment would appear}

^{ན་བཅད་པ་དུ་ མ་དང་མི་ དང་པ་ C8H30 C4H10N" ༢ 195 72.UB13}