EBK ORGANIC CHEMISTRY-PRINT COMPANION (
4th Edition
ISBN: 9781119776741
Author: Klein
Publisher: WILEY CONS
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An unknown compound A (molecular formula C7H14O) was treated with NaBH4 in CH3OH to form compound B (molecular formula C7H16O). Compound A has a strong absorption in its IR spectrum at 1716 cm−1. Compound B has a strong absorption in its IR spectrum at 3600–3200 cm−1. The 1H NMR spectra of A and B are given. What are the structures of A and B?
The bicyclo [3.1.0] hexane ring system, highlighted in compound 3, is found in several natural products, including sabinene, a compound partially responsible for the flavor of ground black pepper. One method for preparing this ring system involves the conversion of compound 1 to compound 2, as shown below. Draw the structure of compound 2 and provide a reasonable mechanism for its formation.
What are the most likely steps in the mechanism to form product 2?
a. protonate, protonate, nucleophilic attack, nucleophilic attack
b. Nucleophilic attack, protonate, protonate, nucleophilic attack
c. Nucleophilic attack, protonate, nucleophilic attack, protonate
d. Protonate, nucleophilic attack, protonate, nucleophilic attack
Two products, A and B, are obtained from the reaction of 1-bromobutane with NH3. Compound A reacts with acetyl chloride to form C, and compound B reacts with acetyl chloride to form D. The IR spectra of C and D are shown. Identify A, B, C, and D.
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