H1-NMR

NMR Lab CHM220 Name: ________________________________
Date: ________________________________
Part 1. Determine the structures for the following compounds based on the 1H-NMR information provided. Fill in the degree of
unsaturation (DU), draw their Lewis structure and try to name the compound.
# peaks 1 2 3 5 7+
Formula Singlet Doublet Triplet Quintet Multiplet DU Lewis Structure Name
6.07, 2H 4.52, 1H
C3H3Cl5
C3H5Cl3
C4H9Br
C10H14
C10H14
C9H11Br
2.20, 3H
4.02, 2H
1.30, 9H
7.28, 5H
1.04, 6H
3.33, 2H
7.12, 5H 0.88, 6H
2.45, 2H
7.22, 5H 2.75, 2H
3.38, 2H
2.15, 2H
1.95, 1H
1.86, 1H

Part 2. Go to the following website http://www.nd.edu/~smithgrp/structure/workbook.html Click on Do the Problems. Answer
questions 1, 3, 4, 7. DO NOT ASK Dr. Structure for help.
Question Lewis Structure Compound Name
1
3
4
7

Part 3. Synthesis and Structure determination
1. The product of the following reaction has a broad absorption at 3330cm -1 in its IR spectrum. Its 13 C-NMR spectrum shows
absorptions at 70 (C), 34 (CH2), 30(CH3), and 15 (CH3). Suggest a structure for this compound.
H2O CH 3
H 3C CH
CH CH 2
H 2SO 4
2. Compound K, molecular formula C6H14O, readily undergoes acid-catalyzed dehydration when warmed with phosphoric acid to give
compound L, molecular formula C6H12, as the major organic product. The 1 H-NMR spectrum of compound K shows signals at δ 0.90
(t, 6H), 1.12 (s, 3H), 1.38 (s, 1H), and 1.48 (q, 4H). The 13 C-NMR spectrum of compound K shows signals at δ 72.98, 33.72, 25.85,
and 8.16. Deduce the structural formulas of compounds K and L.

3. The addition of HCl to but-3-en-2-one gives a product with the following 1H-NMR spectrum. Show the structure of this product,
show a mechanism for its formation, and explain the regiochemistry of the reaction (see section 11.2 in your book).

4. Compound M, molecular formula C5H10O, readily decolorizes in Br2 in CCl4 and is converted by H2/Ni into compound N, molecular
formula C5H12O. Following is the 1 H-NMR spectrum of compound M. The 13 C-NMR spectrum of compound M shows signals at δ
146.2, 110.75, 71.05, and 29.38. Deduce the structural formulas of compounds M and N.

5. Following is the 1 H-NMR spectrum of compound O, molecular formula C7H12. Compound O reacts with bromine in carbon
tetrachloride to give a compound with the molecular formula C7H12Br2. The 13 C-NMR spectrum of compound O shows signals at δ
150.12, 106.43, 35.44, 28.44, and 26.36. Deduce the structural formula of compound O.

6. Treatment of compound P with BH3 followed by H2O2/NaOH gives compound Q. Following are 1 H-NMR spectra from compounds P
and Q along with 13 C-NMR spectral data. From this information, deduce structural formulas for compounds P and Q.
1. BH3 C7H12 C7H14O
2. H2O2, NaOH
13 C-NMR
(P) (Q) (P) (Q)
132.38 72.71
32.12 37.59
29.14 28.13
27.45 22.68