Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 13, Problem 13.50SP
- a. Draw all six isomers of formula C 4 H 8 (including stereoisomers).
- b. For each structure, show how many types of H would appear in the proton NMR spectrum.
- c. For each structure, show how many types of C would appear in the 13 C N M R spectrum.
- d. If an unknown compound of formula C 4 H 8 shows two types of H and three types of C, can you determine its structure from this information?
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
I need help interpreting these 3 spectra, h-nmr,c-nmr, IR. All three correlate to same molecular structure. The question asks you to determine the molecular structure and label all peaks on all 3 spectra.
Connections to biology
5. Tyrosine is an important amino acid in Biochemistry. Assign the peaks in the ¹H-NMR to the hydrogens
in the structure of tyrosine by placing a, b, c, and d in the appropriate corresponding boxes. The
hydrogen atoms attached to O and N atoms do not need to be labeled on this spectrum.
b
14
12
10
d
HN
C
NH₂
histidine
PPM
OH
Propose a structure for the following NMR spectra of a compound with chemical formula
C8H9BR. Draw your final structure in the box. Assign all peaks to atoms in your structure.
Chem.
shift
Rel.
area
1.20
3.00
2.58
2.00
7.07
2.00
7.39
2.00
TMS
10
9.
8.
7
6.
4
1
0 ppm
Chemical shift (8)
TMS
80
60
40
0 ppm
160
140
120
100
200
180
Chemical shift (8)
20
2.
3.
Chapter 13 Solutions
Organic Chemistry (9th Edition)
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
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
- 1. Which proton has the largest multiplicity? Smallest multiplicity? Ha Hd. 2. Which proton has the largest chemical shift? Smallest chemical shift? He Hb Hc N Hf 3. Protons A-E are identified on the spectrum below and correspond to the five unique protons in the molecule shown. (a) Place all the protons on the molecule and categorize them into Ha, Hb, etc. (b) Fill in the table for this molecule (see answer sheet).arrow_forwardWhich structure is consistent with an [M] peak and an [M+2]" peak in the ratlo of 3:17 Click on a letter A through C to answer, А. Br CI В. NH2 С.arrow_forward1. Which proton has the largest multiplicity? Smallest multiplicity? Ha Hd. Hb 2. Which proton has the largest chemical shift? Smallest chemical shift? He Hc Hfarrow_forward
- H H Predict the ¹³C NMR chemical shift of the circled carbon in the structure below. H H I .H H A) 5-40 ppm B) 40-80 ppm C) 110-160 ppm D) 165-180 ppm E) 200-210 ppmarrow_forwardBelow are three MS spectra, Spectra 1, 2, and 3. Each of this mass spectrum corresponds to either Compound A (contains one Cl in the molecular formula), Compound B (one I in the molecular formula), and Compound C (one Br in the molecular formula). Identify which spectra corresponds to which compound. Provide explanations for your choices.arrow_forwardPropose a structure for the following NMR spectrum of a compound with chemical formula C8H9B.. Draw your final structure in the box. Assign all peaks to protons in your structure. Chem. Rel. shift area 3.16 1.00 3.56 1.00 7.18 1.00 7.29 1.50 TMS 10 8. 7 6. 4 1 0 ppm Chemical shift (8) 2. 3.arrow_forward
- 5. Tyrosine is an important amino acid in Biochemistry. Assign the peaks in the 'H-NMR to the hydrogens in the structure of tyrosine by placing a, b, c, and d in the appropriate corresponding boxes. The hydrogen atoms attached to O and N atoms do not need to be labeled on this spectrum. с 11 10 16 00 a H. H- H H -*|| NH₂ Tyrosine d -H ppmarrow_forward7) A molecule has a chemical formula of C6H1202 and produces the spectrum below. Determine its structure. Any labile protons, if they exist, might be present in this 1H NMR spectrum. All signals are singlets. 11 10 HSP-00-610 9 8 7 6 5 ppm 1H 4 -M 3 2H 3H - N 2 6H 1arrow_forwardHow many peaks can be expected in the 13C spectrum of acetylsalicylic acid (shown below)? 1 2 C THO. 7 9. +/- х 100arrow_forward
- Determine the structure of this molecule using the NMR. Please draw the structure and explain how you got it. Thank you for your help!arrow_forwardChemistry H NMR AND C13NMR ??? IN 3 CI 5 A 20= B CI 7 9arrow_forwarda. How many signals are in its 13C NMR spectrum?b. Which signal is at the lowest frequency? CH2=CHBrarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY