Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 14.15, Problem 31P
For each of the following pair of compounds, name one absorption band that can be used to distinguish between them.
- a. CH3CH2CH2CH3 and CH3CH2OCH3
- b. CH3CH2C≡CCH3 and CH3CH2C≡CH
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
2. The following molecule is one enantiomer of methylenedioxymethamphetamine (MDMA).
2a. Circle all of the stereocenters in MDMA
2b. Assign the absolute stereochemistry (R or S) for each stereocenter
.CH3
HN
H
H
*CH3
Compounds 1 and 2 were prepared, and the difference in their heats of combustion was found to be 17.2 kJ/mol (J. Am. Chem. Soc.
1961, 83, 606-614):
H
H
1
Shown below are the lowest-energy conformations of compounds 1 and 2. Identify which drawing matches which compound, and
identify which compound has the larger heat of combustion.
H
H
H
H
|||I
2
H
4
H
H
The first drawing is compound 1, and compound 1 has a larger heat of combustion because it is the less stable compound.
O The first drawing is compound 2, and compound 2 has a larger heat of combustion because it is the less stable compound.
The first drawing is compound 2, and compound 2 has a larger heat of combustion because it is the more stable compound.
The first drawing is compound 1, and compound 1 has a larger heat of combustion because it is the more stable compound.
- Common molecular moieties have easily distinguishable patterns in NMR spectra. Match the
Tollowing hydrocarbons with the generalized spectra shown below. Label each splitting pattem
as a singlet, doublet, triplet, or quartet.
a. X,CH-CHY,
b. X,CH-CH,Y
с. ХCH-CH,Y
d. XCH,CH,
4.0
3.5
3.0
2.5
2.0
1.5
2.0
1.5
1.0
0.5
0.0
5.5
5.0
4.5
4.0
6.0
5.5
5.0
4.5
4.0
Peak b
Chapter 14 Solutions
Organic Chemistry
Ch. 14.1 - Which of the following fragments produced in a...Ch. 14.2 - What distinguishes the mass spectrum of...Ch. 14.2 - What is the most likely m/z value for the base...Ch. 14.3 - Prob. 5PCh. 14.3 - If a compound has a molecular ion with an...Ch. 14.3 - a. Suggest possible molecular formulas for a...Ch. 14.3 - Identify the hydrocarbon that has a molecular ion...Ch. 14.4 - Predict the relative intensities of the molecular...Ch. 14.5 - Which molecular formula has an exact molecular...Ch. 14.5 - Prob. 11P
Ch. 14.6 - Sketch the mass spectrum expected for...Ch. 14.6 - The mass spectra of 1-methoxybutane,...Ch. 14.6 - Prob. 14PCh. 14.6 - Identify the ketones responsible for the mass...Ch. 14.6 - Prob. 16PCh. 14.6 - Using curved arrows, show the principal fragments...Ch. 14.6 - The reaction of (Z)-2-pentene with water and a...Ch. 14.9 - Prob. 19PCh. 14.9 - Prob. 20PCh. 14.9 - Prob. 21PCh. 14.13 - Prob. 22PCh. 14.14 - Which occur at a larger wavenumber: a. the C O...Ch. 14.14 - Prob. 24PCh. 14.14 - Prob. 25PCh. 14.14 - Rank the following compounds from highest...Ch. 14.14 - Which shows an O H stretch at a larger...Ch. 14.15 - Prob. 28PCh. 14.15 - a. An oxygen-containing compound shows an...Ch. 14.15 - Prob. 30PCh. 14.15 - For each of the following pair of compounds, name...Ch. 14.16 - Which of the following compounds has a vibration...Ch. 14.16 - Prob. 33PCh. 14.17 - A compound with molecular formula C4H6O gives the...Ch. 14.19 - Prob. 35PCh. 14.19 - Prob. 36PCh. 14.20 - Predict the max of the following compound:Ch. 14.20 - Prob. 38PCh. 14.21 - a. At pH = 7 one of the ions shown here is purple...Ch. 14.21 - Prob. 40PCh. 14.22 - Prob. 41PCh. 14.22 - Prob. 42PCh. 14 - In the mass spectrum of the following compounds,...Ch. 14 - Prob. 44PCh. 14 - For each of the following pairs of compounds,...Ch. 14 - Draw structures for a saturated hydrocarbon that...Ch. 14 - a. How could you use IR spectroscopy to determine...Ch. 14 - Assuming that the force constant is approximately...Ch. 14 - In the following boxes, list the types of bonds...Ch. 14 - A mass spectrum shows significant peaks at m/z. =...Ch. 14 - Prob. 51PCh. 14 - Prob. 52PCh. 14 - Prob. 53PCh. 14 - How can you use UV spectroscopy to distinguish...Ch. 14 - Rank the following compounds from highest...Ch. 14 - Rank the following compounds from highest...Ch. 14 - What peaks in their mass spectra can be used to...Ch. 14 - Each of the IR spectra shown below is accompanied...Ch. 14 - Prob. 59PCh. 14 - Prob. 60PCh. 14 - How can IR spectroscopy distinguish between...Ch. 14 - 62. Draw the structure of a carboxylic acid that...Ch. 14 - Prob. 63PCh. 14 - Give approximate wavenumbers for the major...Ch. 14 - Prob. 65PCh. 14 - Prob. 66PCh. 14 - Prob. 67PCh. 14 - The IR spectrum of a compound with molecular...Ch. 14 - Which one of the following live compounds produced...Ch. 14 - Prob. 70PCh. 14 - Phenolphthalein is an acid-base indicator. In...Ch. 14 - Which one of the following five compounds produced...Ch. 14 - The IR and mass spectra for three different...
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
- For each organic compound in the table below, enter the locant of the highlighted side chain. compound CH3 1 - CH3 C CH3 CH3 CH3 CH3 - CH - CH₂ CH3 | CH–CH−C– CH 1 CH₂ T CH3 locant of highlighted side chain 0arrow_forwardIdentify the structures of isomers H and I (molecular formula C&HuN). a. Compound H: IR absorptions at 3365, 3284, 3026, 2932, 1603, and 1497 cm 2H 5 H 2H 2H 0 2 3 4 5 6 7 ppm b. Compound I: IR absorptions at 3367, 3286, 3027, 2962, 1604, and 1492 cm1 3 H 5 H 1 H 2 H 3 2 8 5 4 7arrow_forwardWhich of the following compounds has a vibration that is infrared inactive?1-butyne, 2-butyne, H2, H2O, Cl2, and ethenearrow_forward
- 1. Assign the E and Z configuration to the following compounds. HOH-C H₂C NC. H₂CH₂C N E CH3 H CH3 CSN-CHEM 241L-Experiment 7: Stereochemist CH₂OH HOH₂C. CI H₂CO₂C. HO₂C N H OCH3 CH₂CH3arrow_forward7. Assign the E and Z configuration to the following compounds. HOH₂C HOH₂C H₂C NC. H₂CH₂C CH3 H CH3 CH₂OH H₂CO₂C H HO₂C OCH3 K CH₂CH3arrow_forward2) What IR absorption would you use to distinguish between the two compounds above ? CH3 a CH,CCH,CH and b CH;CHCH;CH3arrow_forward
- 10) Which of the following compounds has an S configuration? ÇH3 CI CH3. CH3 CH3 Br CI Br CH H H CH3 CH2CH2CH3 A B Darrow_forwardWhich of these products is the result of a hydride shift occuring during the substitution reaction of aqueous 2-chloro-3-methylpentane? CH3CH2CCH2CH3 || CH2 CH3CH(OH)CH(CH3)CH2CH3 CH2=CHC(CH3)=CHCH3 CH3CH=C(CH3)CH2CH3 CH3CH2C(CH3)CH2CH3 | OHarrow_forward2. Compound B has a molecular formula of C₁H₁2O₂. It has a characteristic IR signal at around 1700 cm³¹. Draw the molecular structure of B. 3H 1H 1H 1H L 200 180 160 140 PPM 120 PPM 100 2H 2H 80 60 2H 40 20arrow_forward
- Point out the most stable conformer from each pair. A CH3 F Н. ΗΤΗ i-Pr с С Н. H CH3 CH3 CH3 CH3 5 i-Pr CH3 ΗΤΗ F 2 H H3C. Н H CH3 CH CH3 CH3 6 в H3C CH3 -Н ну CH3 D 3 Н H3C Br H 7 CI I н CH3 H H3C -Н H3C CH3 H Br H 8 JI -CIarrow_forwardWhich one of these pairs of molecules given below has a more inductive effect? CH3COCH3 or CH3COOH CH3CH2OH or CH3CH2Cl CH3CH2NH2 or CH3CH2F CH3CH2CH2Br or CH3CH2CH2CH2Br CH3CH2CH2F or CH3CH2CH2Cl CH3CH2OH or CH3CH2OCH3 CH3CH2CH2CH2Cl or CH3CH2CH3CHCH2Cl CH3CH2CH2CH2Br OR CH3CH2CH2CH2Cl CH3CH2OH OR CH3CH2NH2arrow_forwardIdentify the structures of isomers H and I (molecular formula C8H11N).a.Compound H: IR absorptions at 3365, 3284, 3026, 2932, 1603, and 1497 cm−1b.Compound I: IR absorptions at 3367, 3286, 3027, 2962, 1604, and 1492 cm−1arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY