Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 9, Problem 13PP
Interpretation Introduction
Interpretation:
Using NMR coupling constants, it is to be explained that how does the given two compounds should be distinguished from one another.
Concept introduction:
Axial bonds are parallel to the axis of ring and equatorial bonds are perpendicular to the axis of ring.
The dihedral angle between two axial bonds is
The coupling constant
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
The 1H and 13C NMR spectra of compound A, C8H9Br are shown below. Answer the following questions.
1(a) Degree of the unsaturation of this compound is = ,
1(b) The derived unsaturation number indicates that compound has ............=
1(c) Two peaks in between 6.5 - 8.0 δ indicate that compound is=
1(d) According to the splitting pattern of the peak at 1.20 δ and 2.58 δ indicates that compound has a .................. group=
1(e) According to the 1H NMR spectrum the number of nonequivalent aromatic proton sets in the compound =
1(f) According to the 13C NMR, the number of nonequivalent carbons in the compound is =
1(g) According to your answer in Q 1(f) the compound has a plane of symmetry Yes or NO =
1(h) The IUAC name for this unknown compound isNOT TOO SURE ABOUT MY ANSWERS, PLEASE CORRECT ME IF I'M WRONG
Нас
3. (5S,7R) -7-bromo-3,9-diethyl-6,6-dimethylundec-3,8-dien-5-ol
H C
Н.С
Ay statuvos
OH
CH3
Ay si
Br
Н
CH3
CH3
I
b. number of peaks =
С.
Both isomeric compounds have the formula C10H14, use the NMR spectra to draw structure of isomer.
Chapter 9 Solutions
Organic Chemistry
Ch. 9 - Prob. 1PPCh. 9 - PRACTICE PROBLEM
9.2 What compound with molecular...Ch. 9 - Prob. 3PPCh. 9 - PRACTICE PROBLEM 9.4 How many signals would each...Ch. 9 - Prob. 5PPCh. 9 - Prob. 6PPCh. 9 - Prob. 7PPCh. 9 - PRACTICE PROBLEM 9.7
The relative chemical shifts...Ch. 9 - Prob. 9PPCh. 9 - PRACTICE PROBLEM 9.9 Propose a structure for...
Ch. 9 - PRACTICE PROBLEM 9.10
What is the dihedral angle...Ch. 9 - PRACTICE PROBLEM 9.11 Draw the most stable chair...Ch. 9 - Prob. 13PPCh. 9 - Prob. 14PPCh. 9 - PRACTICE PROBLEM 9.13 How many signals would you...Ch. 9 - Prob. 16PPCh. 9 - Prob. 17PPCh. 9 - Prob. 18PPCh. 9 - Prob. 19PPCh. 9 - PRACTICE PROBLEM 9.18
What are the expected ratios...Ch. 9 - Given the mass spectrum in Figure 9.44 and the...Ch. 9 - Prob. 22PCh. 9 - 9.23 How many 13C NMR signals would you predict...Ch. 9 - Prob. 24PCh. 9 - 9.25 Propose structures for the compounds G and H...Ch. 9 - Prob. 26PCh. 9 - Prob. 27PCh. 9 - Compound Q has the molecular formula C7H8. The...Ch. 9 - 9.26 Explain in detail how you would distinguish...Ch. 9 - Prob. 30PCh. 9 - A compound with molecular formula C4H8O has a...Ch. 9 - In the mass spectrum of 2, 6-dimethyl-4-heptanol...Ch. 9 - Prob. 33PCh. 9 - What are the masses and structures of the ions...Ch. 9 - Prob. 35PCh. 9 - Ethyl bromide and methoxybenzene (shown below)...Ch. 9 - 9.34 The homologous series of primary amines, ,...Ch. 9 - Propose a structure that is consistent with each...Ch. 9 - 9.39 Propose structures for compounds E and F....Ch. 9 - Regarding compound J, C2HxCly, use the 1H NMR and...Ch. 9 - 9.38 When dissolved in , a compound (K) with the...Ch. 9 - Compound T (C5H8O) has a strong IR absorption band...Ch. 9 - Deduce the structure of the compound that gives...Ch. 9 - 9.45 Deduce the structure of the compound that...Ch. 9 - The 1H NMR spectrum of a solution of 1,...Ch. 9 - Acetic acid has a mass spectrum showing a...Ch. 9 - The 1H NMR peak for the hydroxyl proton of...Ch. 9 - The 1H NMR study of DMF (N, N-dimethylformamide)...Ch. 9 - 9.48 The mass spectra of many benzene derivatives...Ch. 9 - Prob. 52PCh. 9 - 1. Given the following information, elucidate the...Ch. 9 - Two compounds with the molecular formula C5H10O...Ch. 9 - Propose a structure that is consistent with each...Ch. 9 - 9.2 How many 1H NMR signals would the following...Ch. 9 - 9.3. How many 1H NMR signals would...Ch. 9 - 9.4 Which of these C6H14 isomers has the greatest...Ch. 9 - 9.5 How many 13C NMR signals would be given by the...Ch. 9 - Prob. 6QCh. 9 - 9.7 What is the structure of a compound C5H12...
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
- Combined Spectra 14.46 Identify the C3 H5 Br isomers on the basis of the following information: (a) Isomer A has the 'H NMR spectrum shown in 4 Figure 14.49. (b) Isomer B has three peaks in its 13C NMR spectrum: 8 32.6 (CH2 ); 118.8 (CH2 ); and 134.2 (CH). (c) Isomer C has two peaks in its 1°C NMR spectrum: 8 12.0 (CH2) and 16.8 (CH). The peak at lower field is only half as intense as the one at higher field. 10 9. 8 7 6. 5 4 3 2 1 Chemical shift (8, ppm)arrow_forward(c) Each of the following compounds below are characterized by a 'H NMR spectrum that consists of only a single peak having the chemical shift indicated. Identify and draw a bond-line structure for each compound, respectively.. (i) C2H3Cl3-at ~ 2.7 ppm (ii) C5H10-at 1.5 ppmarrow_forwardyou infrared spectroscopy. (a) (b) H distinguish between the following pairs of compounds by using NH2arrow_forward
- Please explain neatly and clearly!!!arrow_forwardPractice Problem 15.45 x Your answer is incorrect. Try again. How many signals do you expect in the ¹H NMR spectrum of the following compound. Isoprene A precursor for natural rubberarrow_forwardFor each of the molecules below: (a) Provide the bond line structures (b) Indicate the number of peaks that would be seen in their ¹H-NMR spectra. Number each unique type of hydrogen peaks as shown in the example on the right. (c) Label the diasterotopic and enantiotopic atoms and/or groups. 1. (1R,4S) 4-secbutyl-2,3-diethyl-6,6-dimethylcyclohex-2-enol 2. (2R,6S) 2,6-dibromo-4,4-dimethylcyclohexanol Example: ¹H 2 O 2 1arrow_forward
- (a) Which molecule shown below is most consistent with the H-NMR spectrum that is shown? (b) Label the C-H in the molecule of your choice, then match the peaks in the NMR spectrum with proper label of the C-H. (Do it on a piece of paper, then scan it into PDF file and upload.) (a) (b) (c) (d) TMS ille 4.400 4.200 4.000 3.800 3.600 3.400 3.200 3.000 2.800 2.600 2.400 2.200 2.000 1.800 1.600 1.400 1.200 1.000 0.800 0.600 0.400 0.200 0.00arrow_forwardThe compound whose 1H NMR spectrum is shown has the molecular formula C7H7Br. Follow the following questions to predict the unknown structure. 2(a) Degree of the unsaturation of this compound is= , 2(b) The two distinct peaks in the aromatic region of the 1H NMR indicate that compound is .................-disubstituted = 2(c) The splitting pattern of the peak at 2.31 δ is = 2(d) The group that corresponds to the splitting pattern in 1(c) is = 2(e) This compound has the plane of symmetry Yes or No = 2(f) The name of the unknown compound =arrow_forwardIII) Can 1H NMR spectroscopy be used to differentiate between the two compounds? Briefly explain why or why not. Predict the 1H NMR spectrum for each compound (include integration, multiplicity, and approximate chemical shift). For each set, be sure that you put them in a data table format!arrow_forward
- Compound A has prominent infrared absorptions at 1050, 1786, and 1852 cm and shows a single absorption in the proton NMR spectrum at 8 3.00. When heated gently with methanol, compound B, C,H,O,, is obtained. Compound B has IR absorptions at 2500–3000 (broad), 1730, and 1701 cm-, and its proton NMR spectrum in D,0 consists of resonances at & 2.7 (complex splitting) and & 3.7 (a singlet) in the intensity ratio 4:3. Give the structures A and B, omitting stereochemistry.arrow_forwardThere are two isometric compounds given below. Discuss how they might be distinguished using IR, 1H NMR and 13C NMR spectroscopy for each compound.arrow_forwardCc.18.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT