Interpretation:
The mechanism for the reaction is to be proposed to account for the formation of the product described in the data from the
Concept introduction:
Sodium borohydride is a reducing agent and is a source of hydride ions (
The
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Organic Chemistry: Principles and Mechanisms (Second Edition)
- When 5-bromopentanal is treated with sodium borohydride, a compound is produced whose 13C NMR spectrum is shown here. In its IR spectrum, no absorption bands appear near 1700 cm-1 or above 3000 cm-1. Propose a mechanism to account for the formation of this product. NABH4 ? H. Br ETOH 200 150 100 50 Chemical shift (ppm) Foarrow_forwardProvide a mechanism for the following transformationarrow_forwardThe following reaction occurs through an E1cb mechanism followed by a tautomerization. Provide a detailed mechanism for the reaction.arrow_forward
- The following transformation involves a conjugate addition to an unusual alkenyl phophonium ion. Provide a detailed mechanism for this transformation, including all proton transfers, intermediates, and byproducts.arrow_forwardWhich reaction sequence would provide the following transformation?arrow_forwardWhen phosgene is treated with excess methanol, a product is formed whose "H NMR spectrum shows one peak-a singlet at 3.8 ppm. Provide a complete, CH,OH ? CI CI detailed mechanism for this reaction. Phosgenearrow_forward
- Treatment of 1,2-dibromoethane with the dithiolate dianion shown in the reaction below leads to two products as shown. Draw the structure for each molecular formula and provide a detailed mechanism for the formation of both products.arrow_forwardIn the presence of an acid catalyst, acetaldehyde forms a trimer known as paraldehyde. Because it induces sleep when it is administered to animals inlarge doses, paraldehyde is used as a sedative or hypnotic. Propose a mechanism for the formation of paraldehyde.arrow_forwardMustard gas, Cl¬CH2CH2¬S¬CH2CH2¬Cl, was used as a poisonous chemical agentin World War I. Mustard gas is much more toxic than a typical primary alkyl chloride. Itstoxicity stems from its ability to alkylate amino groups on important metabolic enzymes,rendering the enzymes inactive.(a) Propose a mechanism to explain why mustard gas is an exceptionally potent alkylatingagentarrow_forward
- Using what you know of carbonyl reactions, propose a mechanism for the processarrow_forwardExplain how benzaldehyde and dimedone reacts with each other, and then with the aminotriazole to form compound 1a in the presence of an acid catalyst. Provide a detailed reaction mechanism and explanation.arrow_forwardProvide a detailed mechanism for the following reaction:arrow_forward
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