Determine a structure that corresponds to the NMR data given format: chemical shift (multiplicity, integration) s=singlet, d=doublet, t=triplet, q=quartet (a) C4H10O δ 1.28 (s, 9H), 1.35 (s, 1H) (b) C3H7Br δ 1.71 (d, 6H), 4.32 (septet, 1H) (c) C4H8O δ 1.05 (t, 3H), 2.13 (s, 3H), 2.47 (q, 2H) IR: 1720 cm-1 (d) C7H8O δ 2.43 (s, 1H), 4.58 (s, 2H), 7.28 (m, 5H) IR: broad 3200-3550 cm-1 (e) C4H9Cl δ 1.04 (d, 6H), 1.95 (m, 1H), 3.35 (d, 2H) (f) C15H14O δ 2.20 (s, 3H), 5.08 (s, 1H), 7.25 (m, 10H) IR: 1720 cm-1 (g) C4H7BrO2 δ 21.08 (t, 3H), 2.07 (m, 2H), 4.23 ( t, 1H), 10.97 (s, 1H) IR: broad peak 2500-3000 cm-1, 1715 cm-1 (h) C8H10 δ 1.25 (t, 3H), 2.68 (q, 2H), 7.23 (m, 5H) (i) C4H8O3 δ 1.27 (t, 3H), 3.66 (q, 2H), 4.13 (s, 2H), 10.95 (s, 1H) IR: broad peak 2500-3000 cm-1, 1715 cm-1 (j) C3H7NO2 δ 1.55 (d, 6H), 4.67 (septet, 1H) (k) C4H10O2 δ 3.25 (s, 6H), 3.45 (s, 4H) (l) C5H10O δ 1.10 (d, 6H), 2,10 ( s, 3H), 2.50 (septet, 1H) IR: 1720 cm-1 (m) C8H9Br δ 2.0 (d, 3H), 5.15 (q, 1H), 7.35 (m, 5H) (n) C7H12O δ 1.08 (s, 6H), 2.21 (d, 2H), 5.08 (d, 1H), 5.11 (d, 1H), 5.75 (t, 1H), 9.49 (s, 1H) IR: 1715 cm-1 (o) C6H14O δ 0.91 (s, 9H), 1.53 (t, 2H), 2.13 (s, 1H), 3.70 (t, 2H) IR: broad peak 3300-3500 cm-1 (p) C6H11N δ 1.45 (s, 2H), 1.63 (pentet, 2H), 1.78 (s, 3H), 2.20 (t, 2H), (2.80 (t, 2H)

IR: 3300 -1 (2 bands), 2200 cm-1 (q) C6H10O δ 0.75 (m, 2H), 1.22 (m, 2H), 1.33 (s, 3H), 2.08 (s, 3H) IR: 1750 cm-1 (r) C7H14O2 δ 0.90 (d, 6H), 1.55 (m, 1H), 1.57 (q, 2H), 2.30 (t, 2H), 3.67 (s, 3H) IR: 1750 cm-1

Answers:

OHBr

(a) (b) (c)

O

(d)

OH

(e)Cl

(f)

Ph

Ph

O

(g)

Br

O

OH(h)

(i)

O

O

OH(j)

NO2

(k)O

O(l)

O

(m)

Ph

Br(n)

O

H (o)

OH

(p)

NH2

(q)

O

(r)

O

OCH3