Student's Solutions Manual for Organic Chemistry
9th Edition
ISBN: 9780134160375
Author: Leroy G. Wade, Jan W. 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
10.
Stereochemistry. Assign R/S stereochemistry for the chiral center indicated on the
following compound. In order to recieve full credit, you MUST SHOW YOUR WORK!
H₂N
CI
OH
CI
カー
11. () Stereochemistry. Draw all possible stereoisomers of the following compound. Assign
R/S configurations for all stereoisomers and indicate the relationship between each as
enantiomer, diastereomer, or meso.
NH2
H
HNH,
-18
b)
8.
Indicate whether the following carbocation rearrangements are likely to occur
Please explain your rational using 10 words or less
not likely to occur
• The double bond is still in the
Same position
+
Likely
to oc
occur
WHY?
-3
H3C
Brave
Chair Conformers. Draw the chair conformer of the following substituted
cyclohexane. Peform a RING FLIP and indicate the most stable
conformation and briefly explain why using 20 words or less.
CI
2
-cobs ??
MUST INDICATE H -2
-2
Br
EQ
Cl
OR
AT
Br
H&
most stable
WHY?
- 4
CH
12
Conformational Analysis. Draw all 6 conformers (one above each letter) of the
compound below looking down the indicated bond. Write the letter of the
conformer with the HIGHEST and LOWEST in energies on the lines provided.
NOTE: Conformer A MUST be the specific conformer of the structure as drawn below
-4 NOT
HOH
OH
3
Conformer A:
Br
OH
A
Samo
Br H
04
Br
H
H3
CH₂
H
anti
stagere
Br CH
clipsed
H
Brott
H
IV
H
MISSING 2
-2
B
C
D
E
F
X
6
Conformer with HIGHEST ENERGY:
13. (1
structure
LOWEST ENERGY:
Nomenclature. a) Give the systematic (IUPAC) name structure. b) Draw the
corresponding to this name. HINT: Do not forget to indicate stereochemistry
when applicable.
a)
८८
2
"Br
{t༐B,gt)-bemn€-nehpརི་ཚ༐lnoa
Parent name (noname)
4 Bromo
Sub = 2-methylethyl-4 Bromo nonane
b) (3R,4S)-3-chloro-4-ethyl-2,7-dimethyloctane
# -2
-2
Chapter 12 Solutions
Student's Solutions Manual for 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
- in the scope of the SCH4U course! please show all steps as im still learning how to format my answers in the format given, thank you!arrow_forwardhelp me solve this HWarrow_forwardMolecules of the form AH2 can exist in two potential geometries: linear or bent. Construct molecular orbital diagrams for linear and bent CH2. Identify the relevant point group, include all of the appropriate symmetry labels and pictures, and fill in the electrons. Which geometry would you predict to be more stable, and why? (Please draw out the diagram and explain)arrow_forward
- Indicate the variation in conductivity with concentration in solutions of strong electrolytes and weak electrolytes.arrow_forwardThe molar conductivity of a very dilute solution of NaCl has been determined. If it is diluted to one-fourth of the initial concentration, qualitatively explain how the molar conductivity of the new solution will compare with the first.arrow_forwardWhat does the phrase mean, if instead of 1 Faraday of electricity, Q coulombs (Q/F Faradays) pass through?arrow_forward
- What characteristics should an interface that forms an electrode have?arrow_forwardFor a weak acid AcH, calculate the dissociated fraction (alpha), if its concentration is 1.540 mol L-1 and the concentration [H+] is 5.01x10-4 mol L-1.arrow_forwardIf the molar conductivity at infinite dilution of HAC is A0 = 390.5 S cm² mol¹. Calculate the Arrhenius conductivity of a 9.3% by weight solution of HAc with a pH of 3.3. Data: molecular weight of HAC is 60.05 g/mol and the density of the solution is 1 g/cm³.arrow_forward
- If the molar conductivity at infinite dilution of HAC is A0 = 390.5 S cm² mol¹. Calculate the Arrhenius conductivity of a 9.3% by weight solution of HAc with a pH of 3.3. Data: molecular weight of HAC is 60.05 g/mol and the density of the solution is 1 g/cm³.arrow_forwardIf the molar conductivity at infinite dilution of HAC is A0 = 390.5 S cm² mol¹. Calculate the Arrhenius conductivity of a 9.3% by weight solution of HAc with a pH of 3.3. Data: molecular weight of HAC is 60.05 g/mol and the density of the solution is 1 g/cm³.arrow_forwardDetermine the distance between the metal and the OHP layer using the Helm- holtz model when the electrode's differential capacitance is 145 μF cm². DATA: dielectric constant of the medium for the interfacial zone &r= lectric constant of the vacuum &0 = 8.85-10-12 F m-1 = 50, die-arrow_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