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A problem set from an organic chemistry course at whittier college, spring 2002, focusing on predicting nmr and ir spectra, identifying products of reactions, and writing reaction mechanisms. Students are required to analyze given spectral data and propose structures for compounds.
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Spring 2002 - Whittier College
September 8, 2003
1a.
OCH 3
1b.
O
O
O
H
1H NMR:
0.91 triplet int 3 2.21 quintet int 2 1.61 doublet (2Hz) int 3 3.05 singlet int 2 2.13 singlet int 3 5.40 complex multiplet int 1
IR:
3050 medium 2965 strong 1732 strong 1656 medium 1406 weak various peaks in the fingerprint region
2a. Did Bob get his desired product? Explain thoroughly. 2b. If not, what product (B) did he get? 2c. Bob washed his product (B) with acid and reanalyzed his product and discovered that he now had a different product with the following NMR:
0.87 triplet (6 hz) int 3 1.15 sextet (6 hz) int 2 1.95 doublet of triplets (6 & 2 Hz) int 2 2.06 doublet (2 hz) int 3 2.12 singlet int 3 5.97 sextet (2 hz) int 1 2c.cont What is the product of this reaction? 2d. Write a mechanism that accounts for the formation of this product.
O (^) 1. Mg / Et 2 O
Compound D. C 10 H 18 O 2.
O
Compound E C 6 H 10 O
Br
Br
3a. What is the structure of compound D? 3b. Write a mechanism that accounts for the formation of compound D. 3c. What is the structure of compound E? 3d. Write a mechanism that accounts for the formation of compound E. 3e. Explain the difference between the two reactions. It may be worthwhile to make models.
Compound F
O
H Compound G
Compound G
Compound H
H 2 / Pd
H 3 O+
Compound H
Compound H PCC
OH
PCC
O
H