The complete, detailed mechanism for the given reaction is to be drawn. The products are to be predicted with the help of the mechanism, paying close attention to stereochemistry. Concept introduction: A carbene is a species containing a carbon atom that has a lone pair of electrons and two bonds. Carbenes are typically highly electrophilic due to the lack of an octet and are sp 2 hybridized. The lone pair of electrons occupies a hybrid orbital, leaving the p orbital empty. Thus, carbenes resemble a carbocation and are generally highly electron-deficient. Chloroform is a precursor to generate a carbene. When an alkyl trihalide is treated with a strong base in the presence of cyclohexane, a dihalocarbene is generated in two steps via α - elimination. The base first deprotonates the alkyl trihalide, which is weakly acidic. In step two, the halogen atom departs to generate a carbene. In an electrophilic addition reaction, alkenes react with carbenes, forming a three-membered ring. The reaction consists of addition of the alkene to an electrophilic carbene. The lone pair can donate back so that a carbocation does not actually form in same step. The stereochemistry of the substituents in the alkene is conserved in the product.

Question

Want to see the full answer?

Answer 1

Question

Chapter 12, Problem 12.3P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn. The products are to be predicted with the help of the mechanism, paying close attention to stereochemistry.

Concept introduction:

A carbene is a species containing a carbon atom that has a lone pair of electrons and two bonds. Carbenes are typically highly electrophilic due to the lack of an octet and are sp2 hybridized. The lone pair of electrons occupies a hybrid orbital, leaving the p orbital empty. Thus, carbenes resemble a carbocation and are generally highly electron-deficient.

Chloroform is a precursor to generate a carbene. When an alkyl trihalide is treated with a strong base in the presence of cyclohexane, a dihalocarbene is generated in two steps via α- elimination. The base first deprotonates the alkyl trihalide, which is weakly acidic. In step two, the halogen atom departs to generate a carbene.

In an electrophilic addition reaction, alkenes react with carbenes, forming a three-membered ring. The reaction consists of addition of the alkene to an electrophilic carbene. The lone pair can donate back so that a carbocation does not actually form in same step. The stereochemistry of the substituents in the alkene is conserved in the product.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

16. The proton NMR spectral information shown in this problem is for a compound with formula CioH,N. Expansions are shown for the region from 8.7 to 7.0 ppm. The normal carbon-13 spec- tral results, including DEPT-135 and DEPT-90 results, are tabulated: 7 J Normal Carbon DEPT-135 DEPT-90 19 ppm Positive No peak 122 Positive Positive cus и 124 Positive Positive 126 Positive Positive 128 No peak No peak 4° 129 Positive Positive 130 Positive Positive (144 No peak No peak 148 No peak No peak 150 Positive Positive してし

3. Propose a synthesis for the following transformation. Do not draw an arrow-pushing mechanism below, but make sure to draw the product of each proposed step (3 points). + En CN CN

Show work..don't give Ai generated solution...