Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 18.4, Problem 18.5P
Synthesis of nitriles by nucleophilic displacement of halide from a haloalkane (also called an
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Synthesis of nitriles by nucleophilic displacement of halide from a haloalkane
(also called an alkyl halide) is practical only with primary and secondary
haloalkanes. It fails with tertiary haloalkanes. Why? What is the major product
of the following reaction?
CH3
KCN
ethanol, water
CI
Which represents an efficient synthetic route to go from an alkane to an alkene?
O elimination with NaNH2, followed by a water workup
O anti-Markovnikov hydrohalogenation, followed by elimination
O radical bromination, followed by elimination
O hydration, followed by elimination
O hydration, followed by ozonolysis of the double bond
Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov
regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called
an enol. The enol immediately rearranges to a more stable ketone via tautomerization.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
-X티
Hö:
H-O
-CH3
-CH3
H30*
Chapter 18 Solutions
Organic Chemistry
Ch. 18.1 - Prob. 18.1PCh. 18.2 - Prob. 18.2PCh. 18.4 - Prob. 18.3PCh. 18.4 - Prob. 18.4PCh. 18.4 - Synthesis of nitriles by nucleophilic displacement...Ch. 18.5 - Complete the following transesterification...Ch. 18.6 - Complete and balance equations for the following...Ch. 18.8 - Prob. AQCh. 18.8 - Several compounds have been found to inhibit...Ch. 18.8 - Prob. CQ
Ch. 18.8 - The following sequence of steps is used to create...Ch. 18.9 - Prob. 18.8PCh. 18.9 - Prob. 18.9PCh. 18.10 - Prob. 18.10PCh. 18.10 - Show how to convert (R)-2-phenylpropanoic acid to...Ch. 18 - Prob. 18.12PCh. 18 - Write the IUPAC name for each compound. (a)...Ch. 18 - Prob. 18.14PCh. 18 - Prob. 18.15PCh. 18 - Propose a structural formula for compound A,...Ch. 18 - Propose a structural formula for compound B,...Ch. 18 - Propose a structural formula for each compound...Ch. 18 - Draw a structural formula for the principal...Ch. 18 - Prob. 18.20PCh. 18 - Prob. 18.21PCh. 18 - Prob. 18.22PCh. 18 - Prob. 18.23PCh. 18 - Prob. 18.24PCh. 18 - Show the product expected when the following...Ch. 18 - The reagent diisobutylaluminum hydride (DIBALH)...Ch. 18 - Prob. 18.27PCh. 18 - Prob. 18.28PCh. 18 - Prob. 18.29PCh. 18 - Nicotinic acid, more commonly named niacin, is one...Ch. 18 - Prob. 18.31PCh. 18 - Prob. 18.32PCh. 18 - Prob. 18.33PCh. 18 - Prob. 18.34PCh. 18 - Prob. 18.35PCh. 18 - Isoniazid, a drug used to treat tuberculosis, is...Ch. 18 - Prob. 18.37PCh. 18 - A step in a synthesis of PGE1 (prostaglandin E1,...Ch. 18 - Prob. 18.39PCh. 18 - Prob. 18.40PCh. 18 - Show how to synthesize 5-nonanone from...Ch. 18 - Prob. 18.42PCh. 18 - The following sequence of steps converts...Ch. 18 - Prob. 18.44PCh. 18 - Prob. 18.45PCh. 18 - Prob. 18.46PCh. 18 - Prob. 18.47PCh. 18 - Following is a retrosynthetic analysis for the...Ch. 18 - Prob. 18.50PCh. 18 - Given this retrosynthetic analysis, propose a...Ch. 18 - Prob. 18.52PCh. 18 - Prob. 18.53PCh. 18 - Prob. 18.54PCh. 18 - In Problem 7.28, we saw this step in Johnsons...Ch. 18 - Prob. 18.56PCh. 18 - Prob. 18.57PCh. 18 - Prob. 18.58PCh. 18 - Prob. 18.59PCh. 18 - Prob. 18.60PCh. 18 - Prob. 18.61PCh. 18 - Prob. 18.62PCh. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Minoxidil is a molecule that causes hair growth in...Ch. 18 - Prob. 18.69PCh. 18 - Prob. 18.70PCh. 18 - Prob. 18.71P
Additional Science Textbook Solutions
Find more solutions based on key concepts
22.102 Write the structures of the cis and tram isomers, if any, for the following compounds:
Chemistry: The Molecular Nature of Matter
How could you separate a mixture of the following compounds? The reagents available to you are water, either, 1...
Organic Chemistry
Practice Exercise 1
Which of the following factors determines the size of an atom? a. the volume of the nucleus...
Chemistry: The Central Science (14th Edition)
The method to determine the volume of a powered solid, liquid and a rock needs to be determined. Concept introd...
Living by Chemistry
Determine the number of protons, neutrons, and electrons in the following atoms: a. a hydrogen atom that has a ...
General, Organic, and Biological Chemistry (3rd Edition)
4. 38 Strontium has four naturally occurring isotopes, with mass numbers 84, 86, 87, arid 88.
a. Write the atom...
Basic Chemistry (5th 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
- CCH H20, H2SO4 H9SO4 CH3 Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Hjö: -CH3 -CH3 H3O*arrow_forwardCan the following alkanes (A and B) be synthesized from the same alkene via a hydrogenation reaction? If this is possible, explain your rationale for why and draw the required alkene. If this is not possible, explain your rationale for why and draw the alkenes required to make each product. Clearly label which alkene would provide which alkane product. CI H3C Is it possible? YES or NO CH3 H3C- H- Rationale: H;C- CH2CH3 CI CH2CH3 A В Alkene(s) Structures:arrow_forward3-Hexanone can be synthesized from butanal and ethane using a Grignard reaction. The first step must be O creation of a carbocation O protonation of an oxygen nucleophilic attack of the aldehyde free radical halogenation preparation of an acetylidearrow_forward
- what is the best way to come up with how to synthesize carboxylic acid , oct-4-yne to butanoic acid, or trans cyclodecene to decanedoic acid . I keep getting confused on how to go from the reactants to product, even with the amines. i can't figure out what to use to get to the product. Please explain Grignard rx as well.arrow_forward10) Synthesis: Make the following products from a suitable cyclic alkene starting material. Look at the functional group PATTERN present in the molecule, including stereochemistry. Br CH3 Br CH3arrow_forwardShow how to control the stereochemistry and regiochemistry (orientation) of additions to alkenes to obtain the products we want.arrow_forward
- How can 3,4-dimethyl-3-nitrohexane be synthesized from butane? Write a scheme for the sequential reactionarrow_forwardA benzene ring alters the reactivity of a neighboring group in the so-called “benzylic” position, similarly to how a double bond alters the reactivity of groups in the “allylic” position. Benzylic cations, anions, and radicals are all more stable than simple alkyl intermediates. a) Use resonance structures to show the delocalization of the positive charge, negative charge, and unpaired electron of the benzyl cation, anion, and radical.arrow_forwardWhat organic product would you obtain from reaction of 1-pentanol with CrO3, H2O, H2SO4?arrow_forward
- Select the best answer. Briefly explain the selection. A mechanism is an acceptable explanation.arrow_forwardC=CH H20, H2SO4 H9SO4 CH3 Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H-OH HO: Hjö: C=CH c=CH Hö Hg Hgarrow_forwardDraw the major organic product formed by reaction of 2-hexyne with the following reagent: H₂O in H₂SO4 / HgSO4. • Consider E/Z stereochemistry of alkenes. • In cases where there is more than one answer, just draw one. • If no reaction occurs, draw the organic starting material.arrow_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
Macroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks Cole
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Macroscale and Microscale Organic Experiments
Chemistry
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Brooks Cole
Alcohols, Ethers, and Epoxides: Crash Course Organic Chemistry #24; Author: Crash Course;https://www.youtube.com/watch?v=j04zMFwDeDU;License: Standard YouTube License, CC-BY