EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
9th Edition
ISBN: 9780136781776
Author: Wade
Publisher: PEARSON CO
expand_more
expand_more
format_list_bulleted
Question
Chapter 13.12F, Problem 13.28P
Interpretation Introduction
Interpretation: The DEPT-90 and DEPT-135 spectra for the given
Concept introduction: NMR spectroscopy is a technique used to determine a 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.
To determine: The DEPT-90 and DEPT-135 spectra for the given
Expert Solution & Answer
![Check Mark](/static/check-mark.png)
Want to see the full answer?
Check out a sample textbook solution![Blurred answer](/static/blurred-answer.jpg)
Students have asked these similar questions
2. READ THE DIRECTIONS TO EACH QUESTION CAREFULLY - not following the directions means you get the question wrong!
3. FORMAT YOUR ANSWERS AS DIRECTED - formatting your answers incorrect means you get the question wrong!
4. Below are the IR regions and NMR chemical shifts table for use with the spectroscopy problems:
'H NMR
12 11
R
20
ΟΞΟ
10
OH R
0=C
H
9 8
7
ppm
6
OH
H C=C-H
5
NH
H-C-X
H-C-O
-OH
X = F, Cl, Br
(i.e. electronegative atom)
3
-NH
2
H-C-N
H-C-S
HC-
1
-CH3
-CH₂-
CEC-H
H-C-C=O -CH
H-C-C=C
0
4000
DID
small range
range of values
broad peak
=C-H
⇓
3250-
3300
N-H
broad with spikes
-3300
-O-H
broad-3300
-3400
3500
-O-H -CEN
N-H CO
I, I
=C
H
2730-
2820
道
H
3000- 2 peaks
3100
-C-H
2850-
2960
0
-C-O-H
broad-3000
3000
usually
strong
-CEN
B
2200
-CICH
3
2200
2500
wavenumber, cm-¹
2000
C
C
HC N
1680
OR
1730
200
C.
H
1600-
1660
0.585
1710
C.
NA₂
1650
3
1600
O
1500
***
1000
These are four alcohols with the formula C4H10O. One of them produced this C-NMR spectrum, which alcohol did that and what carbons correspond with what peaks?
Two bottles labelled cis-cyclohexandiol were found in a
laboratory. Because of their differing melting points, the
bottles clearly contained two different cis-cyclohexandiol
isomers. To determine which isomer was in which bottle,
the chemist decided to run ¹3C NMR spectra on a
sample of each. The three possible products were as in
the figure. (Figure 1)
The two ¹³C NMR proton-decoupled spectra contained
the following data:
●
●
Figure
HO
spectrum of sample in bottle A: 20.20,
62.55
spectrum of sample in bottle B: 16.09,
29.52, 36.15, 63.08
OH
OH
OH
1 of 1
OH
OH
Part A
Identify which isomer was present in the bottle A.
OH
HO
OH
OH
OH
OH
Chapter 13 Solutions
EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
Ch. 13.5A - In a 300-MHz spectrometer, the protons in...Ch. 13.5B - Prob. 13.2PCh. 13.6 - Determine the number of different kinds of protons...Ch. 13.6 - Prob. 13.4PCh. 13.7 - Draw the integral trace expected for the NMR...Ch. 13.7 - Prob. 13.6PCh. 13.8C - Draw the NMR spectra you would expect for the...Ch. 13.8D - Draw the NMR spectra you expect for the following...Ch. 13.8D - a. Assign protons to the peaks in the NMR spectrum...Ch. 13.8D - Prob. 13.10P
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
Similar questions
- The following 1H NMR peaks were recorded on a spectrometer operating at 200 MHz. Convert each into δ units. (a) CHCl3; 1454 Hz (b) CH3Cl; 610 Hz (c) CH3OH; 693 Hz (d) CH2Cl2; 1060 Hzarrow_forwardFollowing is the mass spectrum of an unknown compound. The two highest peaks are at m/z 120 and 122. Suggest a structure for this compound. (Data from http://webbook.nist.gov/chemistry/.)arrow_forwardFollowing is the mass spectrum of bromocyclopentane. The molecular ion m/z 148 is of such low intensity that it does not appear in this spectrum. Assign structural formulas for the cations of m/z 69 and 41.arrow_forward
- When the 1HNMR spectrum of an alcohol is run in dimethylsulfoxide (DMSO) solvent rather than in chloroform, exchange of the Ο-H proton is slow and spin-spin splitting is seen between the Ο-H proton and C-H protons on the adjacent carbon. What spin multiplicities would you expect for the hydroxyl protons in the following alcohols? (a) 2-Methyl-2-propanol (b) Cyclohexanol (c) Ethanol (d) 2-Propanol (e) Cholesterol (f) 1-Methylcyclohexanolarrow_forwardThe mass spectrum and 13C NMR spectrum of a hydrocarbon are shown. Propose a structure for this hydrocarbon, and explain the spectral data.arrow_forwardFollowing is the mass spectrum of 3-methyl-2-butanol. The molecular ion m/z 88 does not appear in this spectrum. Propose structural formulas for the cations of m/z 45, 43, and 41.arrow_forward
- 3-Bromo-1-phenyl-1-propene shows a complex NMR spectrum in which the vinylic proton at C2 is coupled with both the C1 vinylic proton (J = 16 Hz) and the C3 methylene protons (J = 8 Hz). Draw a tree diagram for the C2 proton signal, and account for the fact that a five-line multiplet is observed.arrow_forwardThe proton NMR spectrum in Figure 19-40 is for a compound having an empirical formula C4H7BrO2. Identify the compound.arrow_forward8. Sketch the off-resonance-decoupled 1³C spectra of the following compound. H H C C-H H The splitting pattern of off-resonance decoupled spectrum indicates the number of protons attached to the carbon. 13C nuclei are split only by the protons attached directly to them. The N + 1 rule applies: a carbon with N number of protons gives a signal with N + 1 peaks (e.g. carbon atom with one proton appears as a doublet; carbon with two attached protons gives a triplet etc.) • Carbon atoms with more hydrogens absorb more strongly.arrow_forward
- What Is the correct order (from lowest to highest ppm-value) for the chemical shifts of the labeled carbon atoms In the PC-NMR spectrum of this compound? III O 1.I <|arrow_forwardQ4/ S 204.9 S 162.2 d 136.5 120.0 118.2 131.3 119.2 OH а er I'm 2 26.6 ppm Use the above proton -decoupled Bc spectrum to deduce whether it belongs to compound & or compound Ⓒ. The multiplicity of these signals in the off-resonance Bc spectrum is shown as a letter.arrow_forward11-Explain why 2-chloropropene shows signals for three kinds of protons in its 1H NMRspectrum? Draw the structure and predict the approximate values for 1H-NMR spectra.arrow_forwardarrow_back_iosSEE MORE QUESTIONSarrow_forward_ios
Recommended textbooks for you
- Principles of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
- Macroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks Cole
![Text book image](https://www.bartleby.com/isbn_cover_images/9781305080485/9781305080485_smallCoverImage.gif)
![Text book image](https://www.bartleby.com/isbn_cover_images/9781305577213/9781305577213_smallCoverImage.gif)
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
![Text book image](https://www.bartleby.com/isbn_cover_images/9781305580350/9781305580350_smallCoverImage.gif)
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
![Text book image](https://www.bartleby.com/isbn_cover_images/9781305577190/9781305577190_smallCoverImage.gif)
Macroscale and Microscale Organic Experiments
Chemistry
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Brooks Cole