Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
bartleby

Concept explainers

bartleby

Videos

Textbook Question
Book Icon
Chapter 16, Problem 16.65P

The treatment of isoprene [ CH 2 = C ( CH 3 ) CH = CH 2 ] with one equivalent of mCPBA forms A as the major product. A gives a molecular ion at 84 in its mass spectrum, and peaks at 2850 3150 cm 1 in its IR spectrum. The 1H NMR spectrum of A is given below. What is the structure of A?

Chapter 16, Problem 16.65P, 16.65  The treatment of isoprene  with one equivalent of mCPBA forms  A as the major product. A

Blurred answer
Students have asked these similar questions
Reaction of (CH3)2CO with LiCCH followed by H2O gives compound X, which has a molecular ion in the mass spectrum at 84. It also has prominent absorptions in the IR spectrum at 3600-3200, 3303, 2938, and 2120 cm-1. The proton NMR shows a singlet at 1.53 (6H), a singlet at 2.37 (1H) and a singlet at 2.43 (1H). What is the structure for compound X?
21.95 A student carries out the following sequence of reactions. The IR and 1°C NMR spectra are shown for the product C. Draw structures for A-C. (Remember that the 13C NMR signal at 77 ppm is due to the CDCI3 solvent.) NaOC(CH)3 A (CH3)3COH 1. NaOEt, EtOH 1. NaOH, H,O C В 2. H,0º, A EtO OEt 2. Br(CH,),Br 100 90 80 70 60 – 50 40 - 30 20 C 4500 4000 3500 3000 2500 2000 1500 1000 500 200 175 150 125 100 75 50 25 Wavenumbers (cm-1) Chemical shift (ppm) % Transmittance
Treatment of isobutene [(CH3)2C = CH2] with (CH3)3CLi forms a carbanion that reacts with CH2=O to form H after water is added to the reaction mixture. H has a molecular ion in its mass spectrum at m/z = 86, and shows fragments at 71 and 68. H exhibits absorptions in its IR spectrum at 3600–3200 and 1651 cm−1, and has the 1H NMR spectrum given below. Whatis the structure of H?

Chapter 16 Solutions

Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card

Ch. 16 - Problem 16.11 Neuroprotectin D1 (NPD1) is...Ch. 16 - Problem 16.12 Using hybridization, predict how the...Ch. 16 - Problem 16.13 Use resonance theory to explain why...Ch. 16 - Prob. 16.14PCh. 16 - Prob. 16.15PCh. 16 - Problem 16.16 Draw the products formed when each...Ch. 16 - Problem 16.17 Draw a stepwise mechanism for the...Ch. 16 - Prob. 16.18PCh. 16 - Problem 16.19 Draw the product formed when each...Ch. 16 - Prob. 16.20PCh. 16 - Prob. 16.21PCh. 16 - Problem 16.22 Rank the following dienophiles in...Ch. 16 - Prob. 16.23PCh. 16 - Prob. 16.24PCh. 16 - Problem 16.25 What diene and dienophile are needed...Ch. 16 - Prob. 16.26PCh. 16 - Problem 16.27 Which compound in each pair absorbs...Ch. 16 - Prob. 16.28PCh. 16 - 16.29 Name each diene and state whether the...Ch. 16 - Prob. 16.30PCh. 16 - 16.31 Which of the following systems are...Ch. 16 - 16.32 Draw all reasonable resonance structures for...Ch. 16 - Prob. 16.33PCh. 16 - Prob. 16.34PCh. 16 - 16.35 Explain why the cyclopentadienide anion A...Ch. 16 - Prob. 16.36PCh. 16 - 16.37 Draw the structure of each compound. a. in...Ch. 16 - Prob. 16.38PCh. 16 - 16.39 Label each pair of compounds as...Ch. 16 - Prob. 16.40PCh. 16 - 16.41 Draw the products formed when each compound...Ch. 16 - Prob. 16.42PCh. 16 - 16.43 Treatment of alkenes A and B with gives the...Ch. 16 - 16.44 Draw a stepwise mechanism for the following...Ch. 16 - Prob. 16.45PCh. 16 - 16.46 Explain, with reference to the mechanism,...Ch. 16 - Prob. 16.47PCh. 16 - Prob. 16.48PCh. 16 - Prob. 16.49PCh. 16 - Prob. 16.50PCh. 16 - Prob. 16.51PCh. 16 - Prob. 16.52PCh. 16 - 16.53 Diels–Alder reaction of a monosubstituted...Ch. 16 - Prob. 16.54PCh. 16 - 16.55 Devise a stepwise synthesis of each compound...Ch. 16 - Prob. 16.56PCh. 16 - 16.57 A transannular Diels–Alder reaction is an...Ch. 16 - Prob. 16.58PCh. 16 - Draw a stepwise mechanism for the following...Ch. 16 - Prob. 16.60PCh. 16 - Prob. 16.61PCh. 16 - Prob. 16.62PCh. 16 - Prob. 16.63PCh. 16 - Prob. 16.64PCh. 16 - 16.65 The treatment of isoprene with one...Ch. 16 - 16.66 The treatment of with forms B (molecular...Ch. 16 - Prob. 16.67PCh. 16 - Prob. 16.68PCh. 16 - Prob. 16.69PCh. 16 - Prob. 16.70PCh. 16 - Prob. 16.71PCh. 16 - Prob. 16.72PCh. 16 - Prob. 16.73PCh. 16 - Prob. 16.74PCh. 16 - Prob. 16.75P
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
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
IR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=_TmevMf-Zgs;License: Standard YouTube License, CC-BY