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
Videos
Textbook Question
Chapter 8.14C, Problem 8.34P
Predict the major products of the following reactions, including stereochemistry.
- a. cyclohexene + KMnO4/H2O (cold, dilute)
- b. cyclohexene + peroxyacetic acid in water
- c. cis — pent — 2 — ene + OsO4/H2O2
- d. cis — pent — 2 — ene + peroxyacetic acid in water
- e. trans — pent — 2 ene + OsO4/H2O2
- f. trans — pent — 2 — ene + peroxyacetic acid in water
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Indicate compound A that must react with ethylbenzene to obtain 4-ethylbenzene-1-sulfonic acid.
3-bromo-4-ethylbenzene-1-sulfonic acid.
Part 1 of 2
Draw the structure of A, the minor E1 product of the reaction.
esc
I
Skip Part
Check
H₂O, D
2
A
+
Click and drag to start drawing a
structure.
-0-
F1
F2
1
2
#
3
Q
A
80
F3
W
E
S
D
F4
$
4
%
5
F5
ㅇ
F6
R
T
Y
F
G
X
5
&
7
+
Save
2025 McGraw Hill LLC. All Rights Reserved.
DII
F7
F8
H
*
C
80
J
Z
X
C
V
B
N
4
F9
6
File Preview
The following is a total synthesis of the pheromone of the western pine beetle. Such
syntheses are interesting both because of the organic chemistry, and because of the possibility of
using species specific insecticides, rather than broad band insecticides. Provide the reagents for
each step. There is some chemistry from our most recent chapter in this synthesis, but other
steps are review from earlier chapters. (8 points)
COOEt
COOEt
A
C
COOEt
COOEt
COOH
B
OH
OTS
CN
D
E
See the last homework set
F
for assistance on this one.
H+, H₂O
G
OH
OH
The last step is just nucleophilic addition reactions, taking the
ketone to an acetal, intramolecularly. But
it is hard to visualize the three dimensional shape as
it occurs.
Frontalin, pheromone of the western pine beetle
Chapter 8 Solutions
Organic Chemistry (9th Edition)
Ch. 8.3A - Predict the major products of the following...Ch. 8.3A - a. When 1 mole of buta-1,3-diene reacts with 1...Ch. 8.3B - Predict the major products of the following...Ch. 8.3B - Show how you would accomplish the following...Ch. 8.4B - Propose a mechanism to show how...Ch. 8.4B - Predict the products of the following hydration...Ch. 8.6 - a. Propose a mochansm fortho following reaction....Ch. 8.6 - Prob. 8.8PCh. 8.6 - Prob. 8.9PCh. 8.7A - Prob. 8.10P
Ch. 8.7A - Prob. 8.11PCh. 8.7C - Prob. 8.12PCh. 8.7C - Prob. 8.13PCh. 8.7C - a. When (Z)-3-methylhex-3-ene undergoes...Ch. 8.7C - Prob. 8.15PCh. 8.7C - Prob. 8.16PCh. 8.8B - Prob. 8.17PCh. 8.8B - Prob. 8.18PCh. 8.9 - Prob. 8.19PCh. 8.9 - Prob. 8.20PCh. 8.9 - Prob. 8.21PCh. 8.9 - Prob. 8.22PCh. 8.10 - Prob. 8.23PCh. 8.10 - Prob. 8.24PCh. 8.10 - Prob. 8.25PCh. 8.11A - Prob. 8.26PCh. 8.11B - Prob. 8.27PCh. 8.11B - Prob. 8.28PCh. 8.12 - Prob. 8.29PCh. 8.13 - a. Propose a mechanism for the conversion of...Ch. 8.13 - Magnesium monoperoxyphthalate (MMPP) epoxidizes...Ch. 8.13 - Predict the major products of the following...Ch. 8.13 - When 1,2-epoxycyclohexane (cyclohexene oxide) is...Ch. 8.14C - Predict the major products of the following...Ch. 8.14C - Prob. 8.35PCh. 8.15B - Prob. 8.36PCh. 8.15C - Predict the major products of the following...Ch. 8.16A - Prob. 8.38PCh. 8.16A - Prob. 8.39PCh. 8.16B - Prob. 8.40PCh. 8.16B - Prob. 8.41PCh. 8.16C - Prob. 8.42PCh. 8.17B - Prob. 8.43PCh. 8.17B - Prob. 8.44PCh. 8.17B - Show how you would synthesize each compound,...Ch. 8 - Prob. 8.46SPCh. 8 - Prob. 8.47SPCh. 8 - Give the products expected when the following...Ch. 8 - Show how you would make the following compounds...Ch. 8 - Using 1,2-dimethylcyclohexene as your starting...Ch. 8 - Show how you would synthesize each compound using...Ch. 8 - Prob. 8.52SPCh. 8 - Show how you might use olefin metathesis to...Ch. 8 - Prob. 8.54SPCh. 8 - Prob. 8.55SPCh. 8 - Propose mechanisms consistent with the following...Ch. 8 - Prob. 8.57SPCh. 8 - Prob. 8.58SPCh. 8 - Draw a reaction-energy diagram for the propagation...Ch. 8 - Prob. 8.60SPCh. 8 - Prob. 8.61SPCh. 8 - Prob. 8.62SPCh. 8 - Prob. 8.63SPCh. 8 - Prob. 8.64SPCh. 8 - Prob. 8.65SPCh. 8 - Prob. 8.66SPCh. 8 - Prob. 8.67SPCh. 8 - Prob. 8.68SPCh. 8 - Prob. 8.69SPCh. 8 - Prob. 8.70SPCh. 8 - Prob. 8.71SPCh. 8 - Prob. 8.72SPCh. 8 - Prob. 8.73SPCh. 8 - Prob. 8.74SPCh. 8 - Prob. 8.75SPCh. 8 - Prob. 8.76SPCh. 8 - Prob. 8.77SPCh. 8 - Prob. 8.78SPCh. 8 - Prob. 8.79SP
Additional Science Textbook Solutions
Find more solutions based on key concepts
On what molecule does the anticodon appear? Explain the role of this molecule in protein synthesis.
Human Physiology: An Integrated Approach (8th Edition)
2. Why is it that the range of resting blood pressures of humans is best represented by a bell-shaped curve co...
Human Biology: Concepts and Current Issues (8th Edition)
1. Genetics affects many aspects of our lives. Identify three ways genetics affects your life or the life of a ...
Genetic Analysis: An Integrated Approach (3rd Edition)
Single penny tossed 20 times and counting heads and tails: Probability (prediction): _______/20 heads ________/...
Laboratory Manual For Human Anatomy & Physiology
Why is it unlikely that two neighboring water molecules would be arranged like this?
Campbell Biology (11th Edition)
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 the reaction below: 1. Draw all reasonable elimination products to the right of the arrow. 2. In the box below the reaction, redraw any product you expect to be a major product. C Major Product: Check + ◎ + X ง © Cl I F2 80 F3 I σ F4 I F5 NaOH Click and drawing F6 A 2025 McGraw Hill LLC. All Rights E F7 F8 $ # % & 2 3 4 5 6 7 8 Q W E R T Y U A S D F G H Jarrow_forwardCan I please get help with this graph. If you can show exactly where it needs to pass through.arrow_forwardN Draw the major product of this reaction. Ignore inorganic byproducts. D 1. H₂O, pyridine 2. neutralizing work-up V P W X DE CO e C Larrow_forward
- Draw the major product of this reaction. Ignore inorganic byproducts. N O' 1. H2O, pyridine 2. neutralizing work-up く 8 W aarrow_forwardIdeal Gas Law Practice Name If you need a refresher on Ideal Gas Law, go back to your Ideal Gas Law Reading Assignment from last week! On all of the following, you'll need to make sure to convert pressures to atm and convert temperatures to Kelvin in order to be able to use the R gas constant on your equation sheet! Given: Ideal Gas Law = then P= pressure V = volume R= ideal gas consent PV=nRT namount of substance n=PV/TR P=nRT/V I = temperature V=nRT/P T=PV/nR R=PV/nT 1. What pressure is required to contain 0.023 moles of nitrogen gas in a 4.2 L container at a temperature of 20.°C? 2. Oxygen gas is collected at a pressure of 123 kPa in a container which has a volume of 10.0 L. What temperature must be maintained on 0.500 moles of this gas in order to maintain this pressure? Express the temperature in degrees Celsius. 3. How many moles of chlorine gas would occupy a volume of 35.5 L at a pressure of 100.0 kPa and a temperature of 100. °C? After determining the number of moles,…arrow_forward1. The following conversion includes chemistry we have covered very recently, some chemistry from last term, and chemistry from the first chapter of this unit. Provide curly arrows and an explanation for this mechanism. Use the reagents in the order given. You do not need any other reagents. 1. NaOEt OEt 2.arrow_forward
- COOEt COOEt Step 1 Step 2 Step 3 COOEt COOEt COOH Step 6 OH Step 4 Step 7 (racemic) cyclizes under conditions (8) OTS Step 5 Step 8 ОН OH (racemic) Frontalin (racemic) Shown above are the steps in one of the several published syntheses of Frontalin, a pheromone of the western pine beetle. From the choices provided, show the reagents and conditions by which step 3 of this synthesis might be accomplished. List the reagent(s) in order that will accomplish this transformation. No more than 4 steps are required. List your answer as a single letter (single-step transformation) or a series of letters (multi-step transformation) with no commas separating them. For example, "ab" corresponds to: 1. Eto Na+ 2. NaOH, H₂O NOTE: The order in which you list your letters matters! Reagents: a. Eto Na* g. NaCN b. NaOH, H₂O h. SOCI₂ c. H3O+, heat i. (CH3)2CuLi, ether, -78°C d. LiAlH4 j. H₂O e. p-TsCI, pyridine k. RCO3H f. Br I. H3O+ 1,024arrow_forwardK ← nationa Login - Paymentivet MapQue Draw the major product of this reaction. Ignore inorganic byproducts and the carboxylic acid side product. N 1. excess LiAlH4 2. H₂O ✓ W aarrow_forwardDraw the major product of this reaction. Ignore inorganic byproducts and the alcohol side product. 1. H3O+, heat 2. Neutralizing work-up Drawing Qarrow_forward
- Indicate the procedure (reagent Z) to go from compound A1 to compound A2. A1 Z P(C6H5)3 A2arrow_forwardPlease help with this graph.arrow_forwardogin - PaymentN MapQuest 3 Overview - SAP NetW... Draw the major product of this reaction. Ignore inorganic byproducts. CI 1. NaBH4 2. H₂O C Clever | Portal Job Op Problem Atoms, Bonds and Rings Draw or tap a new bond toarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Coenzymes and cofactors; Author: CH15 SWAYAM Prabha IIT Madras;https://www.youtube.com/watch?v=bubY2Nm7hVM;License: Standard YouTube License, CC-BY
Aromaticity and Huckel's Rule; Author: Professor Dave Explains;https://www.youtube.com/watch?v=7-BguH4_WBQ;License: Standard Youtube License