Warning: foreach() argument must be of type array|object, bool given in /var/www/html/web/app/themes/studypress-core-theme/template-parts/header/mobile-offcanvas.php on line 20

CC(C)=C(C)O (D) C#CCC(=O)[O-] # In this given reaction sequence Pis (A) C=CCCC=O (B) C=CC(C)=O (C) C#CC(C)=C(C)O (D) C#CCC(=O)[O-]

Short Answer

Expert verified
The given reaction sequence involves three main transformations: 1. Hydroboration-oxidation of A (C=CCCC=O) to produce B (C=CC(C)=O), catalyzed by an organoborane and an oxidant like hydrogen peroxide (H2O2) or sodium perborate (NaBO3). 2. Corey–Fuchs reaction to convert B (C=CC(C)=O) into C (C#CC(C)=C(C)O), using carbon tetrabromide (CBr4) and triphenylphosphine (PPh3) for alkyne synthesis. 3. Baeyer-Villiger oxidation of C (C#CC(C)=C(C)O) to form D (C#CCC(=O)[O-]), using peroxy acids like m-chloroperbenzoic acid (MCPBA) as an oxidizing agent to transform the alkene into an ester.

Step by step solution

01

Convert A to B

In this step, we will examine the transformation of A (C=CCCC=O) into B (C=CC(C)=O). The difference between the structures A and B is that one double bond in A is reduced and a methyl group (CH3) is added to the conjugated carbon of the double bond. This suggests that the reaction involved may be a hydrometalation-oxidation sequence that used a reducing agent and an oxidant, like organoboranes (such as 9-borabicyclo[3.3.1]nonane) or diborane, in combination with an oxidant like hydrogen peroxide (H2O2) or sodium perborate (NaBO3), to modify the double bond positions in A.
02

Convert B to C

In this step, we will examine the transformation of B (C=CC(C)=O) into C (C#CC(C)=C(C)O). The difference between the structures B and C is the conversion of a single bond (C-C) into a triple bond (C≡C). This suggests that the reaction involved may be an alkyne synthesis reaction, such as the Corey–Fuchs reaction using carbon tetrabromide (CBr4) and triphenylphosphine (PPh3) for the conversion.
03

Convert C to D

Lastly, we will examine the transformation of C (C#CC(C)=C(C)O) into D (C#CCC(=O)[O-]). The difference between the structures C and D is the conversion of a double bond (C=C) into a carbonyl group (C=O) along with a change in the structure of the attached oxygen atom. This suggests that the reaction involved may be an oxidation reaction, such as the Baeyer-Villiger oxidation using peroxy acids as the oxidizing agent (like m-chloroperbenzoic acid, MCPBA) to transform the alkene into an ester. In summary, the reaction sequence transforming compound A into compound D involves a series of reagents and reaction conditions that help perform hydroboration-oxidation, alkyne synthesis, and Baeyer-Villiger oxidation reactions respectively.

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Over 30 million students worldwide already upgrade their learning with Vaia!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

See all solutions

Recommended explanations on Chemistry Textbooks

View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.

Sign-up for free