ORGANIC CHEMISTRY
9th Edition
ISBN: 9780134645704
Author: WADE AND SIMEK
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 12, Problem 12.23SP
An unknown, foul-smelling hydrocarbon gives the mass spectrum and infrared spectrum shown.
- a. Use the mass spectrum to propose a molecular formula. How many elements of unsaturation are there?
- b. Use the IR spectrum to determine the
functional group (s), if any. - c. Propose one or more structures for this compound. What parts of the structure are uncertain? If you knew that hydrogenation of the compound gives n-octane, would the structure still be uncertain?
- d. Propose structures for the major fragments at 39, 67, 81, and 95 in the mass spectrum.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Draw the two products of the reaction.
H₂C.
CH₂
H
:0:
CH3
CH₂
+1
Show work. Don't give Ai generated solution
None
Chapter 12 Solutions
ORGANIC CHEMISTRY
Ch. 12.3 - Complete the following conversion table. (cm1)...Ch. 12.5 - Which of the bonds shown in red are expected to...Ch. 12.7C - For each hydrocarbon spectrum, determine whether...Ch. 12.9A - Spectra are given for three compounds. Each...Ch. 12.10 - The infrared spectra for three compounds are...Ch. 12.12 - Prob. 12.6PCh. 12.14B - Identify which of these four mass spectra indicate...Ch. 12.15A - Show the fragmentation that accounts for the...Ch. 12.15A - Show the fragmentations that give rise to the...Ch. 12.15B - Ethers are not easily differentiated by their...
Ch. 12.15C - Prob. 12.11PCh. 12 - Prob. 12.12SPCh. 12 - Prob. 12.13SPCh. 12 - All of the following compounds absorb infrared...Ch. 12 - Prob. 12.15SPCh. 12 - Four infrared spectra are shown, corresponding to...Ch. 12 - Predict the masses and the structures of the most...Ch. 12 - Prob. 12.18SPCh. 12 - Prob. 12.19SPCh. 12 - (A true story) While organizing the undergraduate...Ch. 12 - Prob. 12.21SPCh. 12 - Prob. 12.22SPCh. 12 - An unknown, foul-smelling hydrocarbon gives the...Ch. 12 - covered a synthesis of alkynes by a double...Ch. 12 - Three IR spectra are shown, corresponding to three...Ch. 12 - Prob. 12.26SPCh. 12 - Prob. 12.27SPCh. 12 - Prob. 12.28SPCh. 12 - The ultimate test of fluency in MS and IR is...Ch. 12 - Prob. 12.30SPCh. 12 - Consider the following four structures, followed...
Additional Science Textbook Solutions
Find more solutions based on key concepts
An obese 55-year-old woman consults her physician about minor chest pains during exercise. Explain the physicia...
Biology: Life on Earth with Physiology (11th Edition)
Give the IUPAC name for each compound.
Organic Chemistry
Why are mutants used as test organisms in the Ames test?
Laboratory Experiments in Microbiology (12th Edition) (What's New in Microbiology)
Separate the list P,F,V,,T,a,m,L,t, and V into intensive properties, extensive properties, and nonproperties.
Fundamentals Of Thermodynamics
Identify each of the following reproductive barriers as prezygotic or postzygotic. a. One lilac species lives o...
Campbell Essential Biology with Physiology (5th Edition)
Why do scientists think that all forms of life on earth have a common origin?
Genetics: From Genes to Genomes
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
- Question 7 (10 points) Identify the carboxylic acid present in each of the following items and draw their structures: Food Vinegar Oranges Yogurt Sour Milk Pickles Acid Structure Paragraph ✓ BI UAE 0118 + v Task: 1. Identify the carboxylic acid 2. Provide Name 3. Draw structure 4. Take a picture of your table and insert Add a File Record Audio Record Video 11.arrow_forwardCheck the box under each structure in the table that is an enantiomer of the molecule shown below. If none of them are, check the none of the above box under the table. Molecule 1 Molecule 2 IZ IN Molecule 4 Molecule 5 ZI none of the above ☐ Molecule 3 Х IN www Molecule 6 NH Garrow_forwardHighlight each chiral center in the following molecule. If there are none, then check the box under the drawing area. There are no chiral centers. Cl Cl Highlightarrow_forward
- A student proposes the following two-step synthesis of an ether from an alcohol A: 1. strong base A 2. R Is the student's proposed synthesis likely to work? If you said the proposed synthesis would work, enter the chemical formula or common abbreviation for an appropriate strong base to use in Step 1: If you said the synthesis would work, draw the structure of an alcohol A, and the structure of the additional reagent R needed in Step 2, in the drawing area below. If there's more than one reasonable choice for a good reaction yield, you can draw any of them. ☐ Click and drag to start drawing a structure. Yes No ロ→ロ 0|0 G Х D : ☐ பarrow_forwardटे Predict the major products of this organic reaction. Be sure to use wedge and dash bonds when necessary, for example to distinguish between different major products. ☐ ☐ : ☐ + NaOH HO 2 Click and drag to start drawing a structure.arrow_forwardShown below are five NMR spectra for five different C6H10O2 compounds. For each spectrum, draw the structure of the compound, and assign the spectrum by labeling H's in your structure (or in a second drawing of the structure) with the chemical shifts of the corresponding signals (which can be estimated to nearest 0.1 ppm). IR information is also provided. As a reminder, a peak near 1700 cm-1 is consistent with the presence of a carbonyl (C=O), and a peak near 3300 cm-1 is consistent with the presence of an O–H. Extra information: For C6H10O2 , there must be either 2 double bonds, or 1 triple bond, or two rings to account for the unsaturation. There is no two rings for this problem. A strong band was observed in the IR at 1717 cm-1arrow_forward
- Predict the major products of the organic reaction below. : ☐ + Х ك OH 1. NaH 2. CH₂Br Click and drag to start drawing a structure.arrow_forwardNG NC 15Show all the steps you would use to synthesize the following products shown below using benzene and any organic reagent 4 carbons or less as your starting material in addition to any inorganic reagents that you have learned. NO 2 NC SO3H NO2 OHarrow_forwardDon't used hand raiting and don't used Ai solutionarrow_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
Mass Spectrometry; Author: Professor Dave Explains;https://www.youtube.com/watch?v=hSirWciIvSg;License: Standard YouTube License, CC-BY