The product expected with its stereochemistry when cyclopentene reacts with NBS and water. Concept introduction: NBS can be used as a source of bromine, as it is stable, easily handled compound that slowly decompose in aqueous dimethylsulphoxide to yield bromine at controlled rate. Bromine from NBS adds on to the double bond to give a cyclic bromonium ion. Water, being a nucleophile, attacks the bromonium ion from the unshielded side to give an intermediate which loses a proton to yield a bromohydrin as the product. The addition occurs with anti stereochemistry resulting in a trans- product. To give: The product expected with its stereochemistry when cyclopentene reacts with NBS and water.

Question

Complete boxes in the flow chart. Draw the structure of the organic compound foundin each layer after adding 3M NaOH and extraction. Make sure to include any charges. Provide explanation on answers.

Answer 1

Question

Chapter 8.3, Problem 5P

Interpretation Introduction

Interpretation:

The product expected with its stereochemistry when cyclopentene reacts with NBS and water.

Concept introduction:

NBS can be used as a source of bromine, as it is stable, easily handled compound that slowly decompose in aqueous dimethylsulphoxide to yield bromine at controlled rate. Bromine from NBS adds on to the double bond to give a cyclic bromonium ion. Water, being a nucleophile, attacks the bromonium ion from the unshielded side to give an intermediate which loses a proton to yield a bromohydrin as the product. The addition occurs with anti stereochemistry resulting in a trans- product.

To give:

The product expected with its stereochemistry when cyclopentene reacts with NBS and water.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

Complete boxes in the flow chart. Draw the structure of the organic compound foundin each layer after adding 3M NaOH and extraction. Make sure to include any charges. Provide explanation on answers.

== Vid4Q2 Unanswered ☑ Provide IUPAC name of product in the reaction below A 3,4-dimethylcyclohexene B 1,2-dimethylcyclohexane C 1,2-dimethylcyclohexene D 3,4-dimethylcyclohexane H₂ Pd

5. Use the MS data to answer the questions on the next page. 14.0 1.4 15.0 8.1 100- MS-IW-5644 26.0 2.8 27.0 6.7 28.0 1.8 29.0 80 4.4 38.0 1.0 39.0 1.5 41.0 1.2 42.0 11.2 43.0 100.0 44.0 4.3 79.0 1.9 80.0 2.6 Relative Intensity 40 81.0 1.9 82.0 2.5 93.0 8.7 20- 95.0 8.2 121.0 2.0 123.0 2.0 136.0 11.8 0 138.0 11.5 20 40 8. 60 a. Br - 0 80 100 120 140 160 180 200 220 m/z Identify the m/z of the base peak and molecular ion. 2 b. Draw structures for each of the following fragments (include electrons and charges): 43.0, 93.0, 95.0, 136.0, and 138.0 m/z. C. Draw a reasonable a-fragmentation mechanism for the fragmentation of the molecular ion to fragment 43.0 m/z. Be sure to include all electrons and formal charges. 6. Using the values provided in Appendix E of your lab manual, calculate the monoisotopic mass for the pyridinium ion (CsH6N) and show your work.