STRUCTURAL DETERMINATION

Strategy:

1) Use IHD ______________________________ to determine if a ring or double or triple bond is present.

2) If an IR spectrum is provided use it to determine possible functional groups. 3) Use the integration of hydrogens to determine their split pattern. 4) Start Drawing!!!

1) Propose structures for compounds that fit the following 1H NMR data:

a) Formula: C4H6Cl2 1H NMR: 2.18 δ (3H, singlet) 4.16 δ (2H, doublet)

5.71 (1H, triplet)

b) Formula: C10H141H NMR: 1.30 δ (9H, singlet)

7.30 δ (5H, singlet)

c) Formula: C4H7BrO 1H NMR: 2.11 δ (3H, singlet)

3.52 δ (2H, triplet) 4.40 δ (2H, triplet)

d) Formula: C9H11Br 1H NMR: 2.15 δ (2H, quintet)

2.75 δ (2H, triplet) 3.38 δ (2H, triplet)

7.22 δ (5H, multiplet)

e) Formula: C5H10O 1H NMR: 0.95 δ (6H, doublet)

2.10 δ (3H, singlet) 2.43 δ (1H, multiplet)

f) Formula: C3H5Br 1H NMR: 2.32 δ (3H, singlet)

5.35 δ (1H, singlet)

5.54 δ (1H, singlet)

g) Formula: C11H14O IR: 1730 cm-1 1H NMR: 1.3 ppm (9H, singlet)

7.5 ppm (2H, doublet)

7.7 ppm (2H, doublet)

9.9 ppm (1H, singlet)

h) Formula: C5H8O2 IR: 1730 cm-1 1H NMR: 2.1 ppm (1H, singlet)

3.6 ppm (3H, singlet)

i) Formula: C4H11N IR: 3400 cm-1 1H NMR: 1.0 ppm (6H, singlet)

2.1 ppm (1H, multiplet)

2.6 ppm (2H, doublet)

2.0 ppm (2H, singlet)

j) Formula: C5H10O2 IR: 1750 cm-1 1H NMR: 1.1 ppm (3H, triplet)

1.3 ppm (3H, triplet) 2.3 ppm (2H, quartet)4.1 ppm (2H, quartet)

k) Formula: C5H10O2 IR: 1700 cm-1 1H NMR: 2.2 ppm (2H, triplet)

1.56 ppm (2H, multiplet) 1.33 ppm (2H, multiplet) 1.0 ppm (3H, triplet)

11.0 ppm (1H, singlet)