The alkyne, which, when treated with diazomethane and irradiated with UV light, will produce the given compound, is to be drawn. A full mechanism for the reaction is to be drawn. Concept introduction: A cyclopropyl ring can be introduced in a product by treating the corresponding alkene or alkyne with a carbene. A carbene is a reactive species with two groups, mostly hydrogens or halogens, bonded to a carbon that also has a lone pair of electrons. Since the carbon lacks an octet of electrons, it acts as an electrophile. At the same time, the lone pair on it also gives it a nucleophilic character. Carbenes react with alkenes and alkynes to replace the π bond with two C − C σ bonds and form a cyclopropyl ring. A carbene is a highly reactive, transient species and must be generated in situ. A common method of generating a carbene is to irradiate diazomethane with UV light. The C − N bond breaks heterolytically to produce the carbene and a molecule of nitrogen.

Question

Want to see the full answer?

Answer 1

Question

Chapter 12, Problem 12.30P

Interpretation Introduction

Interpretation:

The alkyne, which, when treated with diazomethane and irradiated with UV light, will produce the given compound, is to be drawn. A full mechanism for the reaction is to be drawn.

Concept introduction:

A cyclopropyl ring can be introduced in a product by treating the corresponding alkene or alkyne with a carbene. A carbene is a reactive species with two groups, mostly hydrogens or halogens, bonded to a carbon that also has a lone pair of electrons. Since the carbon lacks an octet of electrons, it acts as an electrophile. At the same time, the lone pair on it also gives it a nucleophilic character. Carbenes react with alkenes and alkynes to replace the π bond with two C−C σ bonds and form a cyclopropyl ring.

A carbene is a highly reactive, transient species and must be generated in situ. A common method of generating a carbene is to irradiate diazomethane with UV light. The C−N bond breaks heterolytically to produce the carbene and a molecule of nitrogen.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Predict the organic product that forms in the reaction below: H + гон OH H+ H+ ☑ O Note: You may assume you have an excess of either reactant if the reaction requires more than one of those molecules to form the product. In the drawing area below, draw the skeletal ("line") structure of the missing organic product X. Explanation Check Click and drag to start drawing a structure. S 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Cente

In the analysis of Mg content in a 25 mL sample, a titration volume of 5 mL was obtained using 0.01 M EDTA. Calculate the Mg content in the sample if the Ca content is 20 ppm

Predict the organic products that form in the reaction below: H. H+ + OH H+ Y Note: You may assume you have an excess of either reactant if the reaction requires more than one of those molecules to form the products. In the drawing area below, draw the skeletal ("line") structures of the missing organic products X and Y. You may draw the structures in any arrangement that you like, so long as they aren't touching. Explanation Check Click and drag to start drawing a structure. G X C © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Access +