Organic Chemistry
8th Edition
ISBN: 9781337516402
Author: Brown
Publisher: Cengage
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
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*
Can 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:
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
- CH3 CH3 Br- Br2 .CH3 CH2Cl2 CH3 H3C H3C Br Electrophilic addition of bromine, Brɔ, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl,. In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CH3 CH3 CH3 CH3 H3C H3C :Br: :Br:arrow_forwardYou are required to synthesize 2-bromopentane from the reaction between an alkene with HBr. Which alkene, 1-pentene or 2-pentene, should you react with HBr in order to get 2-bromopentane? Give an explanation.arrow_forwardwhat 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_forward
- CH3 Ph3P-CHCH3 H3C H3C Aldehydes and ketones are converted into alkenes by means of a direct nucleophilic addition called the Wittig reaction. In the reaction, a triphenylphosphorine ylide, also called a phosphorane, adds to an aldehyde/ketone to give a four-membered cyclic intermediate called an oxaphosphetane. The oxaphosphetane is not isolated but instead spontaneously decomposes to release triphenylphosphine oxide and an alkene. Ph3P-CHCH3 H3C The ylide is formed by reaction of triphenylphosphine, a good nucleophile, with a primary alkyl halide in an S 2 reaction, followed by deprotonation of the carbon with a strong base, such as butyllithium. The carbonyl carbon and the carbon originally bonded to the halogen become the two carbons with the double bond in the product alkene :0: CH3 Com The real value of the Wittig reaction lies in its ability to yield an alkene of predictable structure, as the C-C bond is precisely where the C=O bond was in the reactant and no isomers (other than…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_forwardWhen you react ammonia with a halogenated Alkane will you get only one organic product? Why or why notarrow_forward
- Show how to control the stereochemistry and regiochemistry (orientation) of additions to alkenes to obtain the products we want.arrow_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
- C=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_forwardChoose the two alkyl bromides and the hydrogenation method that must be used to synthesize these alkenes from acetylene.Enter your answer as two letters in alphabetical order, followed by a number; i.e. ac2, not ca2. Do not use punctuation.arrow_forwardAll electrophilic aromatic substitution reactions occur via a two-step mechanism: addition of the electrophile to form a resonance-stabilized carbocation, followed by deprotonation by a base. In the step shown below, loss of a proton to form the substitution product was drawn using the resonance structure with the + 1 formal charge at the ortho position to the carbon bonded to the electrophile. Redraw the step shown with the other two resonance structures and use curved arrows to show how these other two resonance structures can be converted to the substitution product by removal of a proton with the base shown. Part: 0/2 Part 1 of 2 H :CI-AICI, Draw the mechanism that generates the final substitution product with the +1 formal charge at the para position. Cl HC1 AICI3arrow_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