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 (3H, singlet) 4.16 (2H, doublet) 5.71 (1H, triplet)

b) Formula: C10H14

1H

NMR: 1.30 (9H, singlet) 7.30 (5H, singlet)

c) Formula: C4H7BrO

1H

NMR: 2.11 (3H, singlet) 3.52 (2H, triplet) 4.40 (2H, triplet)

d) Formula: C9H11Br

1H

NMR: 2.15 (2H, quintet) 2.75 (2H, triplet) 3.38 (2H, triplet) 7.22 (5H, multiplet)

e) Formula: C5H10O

1H

NMR: 0.95 (6H, doublet) 2.10 (3H, singlet) 2.43 (1H, multiplet)

f) Formula: C3H5Br

1H

NMR: 2.32 (3H, singlet) 5.35 (1H, singlet) 5.54 (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)