Organic Chemistry (9th Edition)
Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
bartleby

Concept explainers

bartleby

Videos

Textbook Question
Book Icon
Chapter 13, Problem 13.33SP

An unknown compound has the molecular formula C 9 H 11 B r. Its proton NMR spectrum shows the following absorptions:

singlet, δ 7.1, integral 44 mm

singlet, δ 2.3, integral 130 mm

singlet, δ 2.2, integral 67 mm

Propose a structure for this compound.

Expert Solution & Answer
Check Mark
Interpretation Introduction

Interpretation:

The structure of the given unknown compound showing the given absorptions in the NMR spectrum is to be proposed.

Concept introduction:

NMR spectroscopy is a technique used to determine the unique structure of the compounds. It identifies the carbon-hydrogen bonding of an organic compound. A hydrogen atom is called as a proton in the NMR spectroscopy.

Answer to Problem 13.33SP

The structure of the given unknown compound showing the given absorptions in the NMR spectrum is given below.

Explanation of Solution

The molecular formula of the compound (C9H11Br).

The double bond equivalent is calculated by the formula,

DBE=(Numberofcarbonatoms(Numberofhydrogenorhalogenatoms2)+(Numberofnitrogenatoms2)+1)

Substitute the given values in the above expression.

DBE=(Numberofcarbonatoms(Numberofhydrogenorhalogenatoms2)+(Numberofnitrogenatoms2)+1)=9112+12=4

The DBE value is more than three and one signal present at δ7.1ppm shows that the molecule has one benzene ring.

The other signals present in the NMR spectrum shows that,

δ7.1ppm indicates that the number of protons is 2.

δ2.3ppm indicates that the number of protons is 6.

δ2.2ppm indicates that the number of protons is 3.

From the above data analysis of 13C NMR spectrum, the structure of compound which shows the above signals is given as,

Organic Chemistry (9th Edition), Chapter 13, Problem 13.33SP

Figure 1

Conclusion

The structure of the given unknown compound showing the given absorptions in the NMR spectrum has been rightfully stated.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!
Students have asked these similar questions
The 1H-NMR spectrum of Compound C shows five signals – δ 2.38 (1H, dt), 2.72 (1H, dt), 5.34 (1H, t), 5.49 (2H, ddd), 6.27 (2H, dd) ppm. Its 13C-NMR spectrum has four signals – δ 26, 58, 127, 129 ppm. In the compound’s mass spectrum, the M+1 peak appears at m/z = 115. An M+2 peak, whose intensity is roughly one-third that of the M+1 peak, also appears. Suggest a structure for this compound.
Deduce the structure of a compound with molecular formula C5H100 that exhibits the following ¹H and ¹³C NMR spectra. IH NMR CNMR 150 10 Structure A Structure B Structure C Structure D 24 1C 100 B 2H H 20 50 10 D 311
Propose a structure given the 1H and 13C NMR spectra of the unknown compound. Assign chemical shifts to corresponding hydrogen and carbon atoms Molecular Formula: C5H10O3

Chapter 13 Solutions

Organic Chemistry (9th Edition)

Ch. 13.8D - Two spectra are shown. Propose a structure that...Ch. 13.9 - Prob. 13.12PCh. 13.9 - The spectrum of trans-hex-2-enoic acid follows. a....Ch. 13.9 - Prob. 13.14PCh. 13.9 - Prob. 13.15PCh. 13.10 - Prob. 13.16PCh. 13.10 - If the imaginary replacement of either of two...Ch. 13.10 - Predict the theoretical number of different NMR...Ch. 13.11B - Prob. 13.19PCh. 13.11B - Prob. 13.20PCh. 13.11B - Prob. 13.21PCh. 13.11B - Prob. 13.22PCh. 13.11B - Prob. 13.23PCh. 13.11B - Prob. 13.24PCh. 13.12E - Draw the expected broadband-decoupled 13 C N M R...Ch. 13.12E - a. Show which carbon atoms correspond with which...Ch. 13.12E - Repeat Problem13-25, sketching the...Ch. 13.12F - Prob. 13.28PCh. 13.13 - A bottle of allyl bromide was found to contain a...Ch. 13.13 - A laboratory student was converting cyclohexanol...Ch. 13.14 - Sets of spectra are given for two compounds. For...Ch. 13 - An unknown compound has the molecular formula C 9...Ch. 13 - Prob. 13.34SPCh. 13 - Predict the approximate chemical shifts of the...Ch. 13 - Prob. 13.36SPCh. 13 - Prob. 13.37SPCh. 13 - Prob. 13.38SPCh. 13 - Prob. 13.39SPCh. 13 - Prob. 13.40SPCh. 13 - For each compound shown below. 1. sketch the 13 C...Ch. 13 - Prob. 13.42SPCh. 13 - Prob. 13.43SPCh. 13 - Prob. 13.44SPCh. 13 - Prob. 13.45SPCh. 13 - Prob. 13.46SPCh. 13 - A compound was isolated as a minor constituent in...Ch. 13 - Prob. 13.48SPCh. 13 - The three isomers of dimethylbenzene are commonly...Ch. 13 - a. Draw all six isomers of formula C 4 H 8...Ch. 13 - Prob. 13.51SPCh. 13 - Hexamethylbenzene undergoes free-radical...Ch. 13 - Each of these four structures has molecular...Ch. 13 - Prob. 13.54SPCh. 13 - Phenyl Grignard reagent adds to 2-methylpropanal...Ch. 13 - Prob. 13.56SP
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: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
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY