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: C10H14
1H
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)
1H
f) Formula: C3H5Br
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)
