EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
9th Edition
ISBN: 8220100591310
Author: McMurry
Publisher: CENGAGE L
bartleby

Concept explainers

Question
Book Icon
Chapter 8.3, Problem 6P
Interpretation Introduction

Interpretation:

Given that, when an unsymmetrical alkene such as propene is treated with NBS in aqueous dimethyl sulfoxide, the major product has the bromine atom bonded to the less highly substituted carbon atom. Whether the orientation is Markovnikov or non-Markovnikov is to be explained.

Concept introduction:

NBS can be used as a source of bromine, as it is stable, easily handled compound that slowly decompose in aqueous dimethyl sulfoxide 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.

According to Markovnikov rule, in the addition of HX to unsymmetrical alkenes the H (positive part) attaches itself to the carbon with fewer alkyl substituents and X (negative part) attaches itself to the carbon with more alkyl substituents.

To explain:

Whether the orientation of groups in the addition reaction between propene and NBS in aqueous dimethyl sulfoxide ,where in the major product has the bromine atom bonded to the less highly substituted carbon atom, is Markovnikov or non-Markovnikov.

Blurred answer
Students have asked these similar questions
The electron of a hydrogen atom is excited to the 4d orbital. Calculate the energy of the emitted photon if the electron were to move to each of the following orbitals: (a) 1s; (b) 2p; (c) 2s; (d) 4s. (e) Suppose the outermost electron of a potassium atom were excited to a 4d orbital and then moved to each of these same orbitals. Describe qualitatively the differences that would be found between the emission spectra of potassium and hydrogen (do not perform calculations). Explain your answer.
Imagine a four-dimensional world. In it, atoms would have one s orbital and four p orbitals in a given shell. (a) Describe the shape of the Periodic Table of the first 24 elements. (b) What elements would be the first two noble gases (use the names from our world that correspond to the atomic numbers).
The electron affinity of thulium was measured by a technique called laser photodetachment electron spectroscopy. In this technique, a gaseous beam of anions of an element is bombarded with photons from a laser. The photons knock electrons off some of the anions, and the energies of the emitted electrons are detected. The incident radiation had a wavelength of 1064 nm, and the emitted electrons had an energy of 0.137 eV. Although the analysis is more complicated, we can obtain an estimate of the electron affinity from the energy difference between the photons and the emitted electrons. What is the electron affinity of thulium in electron volts and in kilojoules per mole?

Chapter 8 Solutions

EBK ORGANIC CHEMISTRY

Ch. 8.5 - Tho following cycloalkene gives a mixture of two...Ch. 8.6 - Prob. 12PCh. 8.7 - Prob. 13PCh. 8.7 - Starting with an alkene, how would you prepare...Ch. 8.8 - Prob. 15PCh. 8.8 - Prob. 16PCh. 8.9 - What products would you expect from the following...Ch. 8.10 - Prob. 18PCh. 8.10 - Prob. 19PCh. 8.13 - Prob. 20PCh. 8.13 - What products are formed from hydration of...Ch. 8.SE - Name the following alkenes, and predict the...Ch. 8.SE - Prob. 23VCCh. 8.SE - Prob. 24VCCh. 8.SE - Prob. 25VCCh. 8.SE - Prob. 26MPCh. 8.SE - Prob. 27MPCh. 8.SE - Draw the structures of the organoboranes formed...Ch. 8.SE - Prob. 29MPCh. 8.SE - Provide the mechanism and products for the...Ch. 8.SE - Propose a curved-arrow mechanism to show how ozone...Ch. 8.SE - Prob. 32MPCh. 8.SE - Prob. 33MPCh. 8.SE - Prob. 34MPCh. 8.SE - 10-Bromo- α -chamigrene, a compound isolated from...Ch. 8.SE - Isolated from marine algae, prelaureatin is...Ch. 8.SE - Dichlorocarbene can be generated by heating sodium...Ch. 8.SE - Reaction of cyclohexene with mercury(II) acetate...Ch. 8.SE - Use your general knowledge of alkene chemistry to...Ch. 8.SE - Prob. 40MPCh. 8.SE - Hydroboration of 2-methyl-2-pentene at 25°C,...Ch. 8.SE - Prob. 42APCh. 8.SE - Suggest structures for alkenes that give the...Ch. 8.SE - Prob. 44APCh. 8.SE - Prob. 45APCh. 8.SE - Prob. 46APCh. 8.SE - Prob. 47APCh. 8.SE - Predict the products of the following reactions....Ch. 8.SE - Prob. 49APCh. 8.SE - How would you carry out the following...Ch. 8.SE - Draw the structure of an alkene that yields only...Ch. 8.SE - Show the structures of alkenes that give the...Ch. 8.SE - Prob. 53APCh. 8.SE - Which of the following alcohols could not be made...Ch. 8.SE - Prob. 55APCh. 8.SE - Prob. 56APCh. 8.SE - Prob. 57APCh. 8.SE - Compound A has the formula C10HI6. On catalytic...Ch. 8.SE - Prob. 59APCh. 8.SE - Prob. 60APCh. 8.SE - Prob. 61APCh. 8.SE - Draw the structure of a hydrocarbon that absorbs 2...Ch. 8.SE - Prob. 63APCh. 8.SE - The sex attractant of the common housefly is a...Ch. 8.SE - Prob. 65APCh. 8.SE - Prob. 66APCh. 8.SE - α-Terpinene, C10H16, is a pleasant-smelling...Ch. 8.SE - Prob. 68APCh. 8.SE - Prob. 69APCh. 8.SE - Prob. 70APCh. 8.SE - Prob. 71APCh. 8.SE - Prob. 72AP
Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
  • Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305080485
    Author:John E. McMurry
    Publisher:Cengage Learning
    Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305580350
    Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
    Publisher:Cengage Learning
    Text book image
    Organic Chemistry: A Guided Inquiry
    Chemistry
    ISBN:9780618974122
    Author:Andrei Straumanis
    Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Text book image
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning