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:

O OH
(a) (b) (c)
OH (d)
Br

Ph O
(e) (g) (h)
(f)
Cl Ph OH

O Br

(i) O
(j) (k) (l)
OH O
O NO2 O
O

Br
(m) (n) (o) (p)
H
Ph
OH
O NH2

(q) (r)
O
CH3
O
O