EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 22, Problem 22.69AP
Interpretation Introduction
Interpretation:
The reason corresponding to the fact that the reaction between
Concept introduction:
In
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Grignard reagent is a versatile tool in synthetic organic chemistry. Using bromocyclopentane as a starting material, show how a Grignard reagent, X, is synthesized.
Reaction of X with water produces compound Y while treatment in carbon dioxide followed by hydrolysis forms compound Z. 3-methyl-2butanone reacts with X and hydrolyses to yield compound AA. Draw the structural formulae of compounds Y, Z and AA and write the chemical equations respectively.
When 2-bromo-2-methylbutane is treated with a base, a mixture of 2-methyl-2-butene and 2-methyl-1-
butene is produced. When potassium hydroxide is the base, 2-methyl-1-butene accounts for 45% of the
product mixture. However, when potassium tert-butoxide is the base, 2-methyl-1-butene accounts for
70% of the product mixture. What percent of 2-methyl-1-butene would be in the mixture if potassium
propoxide were the base?
base
Br
A.
Less than 45%
B.
C.
45%
Between 45% and 70%
D.
More than 70%
Structure of
product C
A hydrocarbon, A, with formula C11H16
undergoes hydrogenation with Pd to give
product B, C11H22, and with Lindlar's
catalyst to give product C, C11 H18.
Ozonolysis leads to a mixture of
products including cyclohexanone and
4-oxobutanoic acid. Treatment with
sodium amide (NaNH2) followed by
bromoethane gives compound D, C13H20.
Draw possible structures for A, B, C, and
D.
H₂,
Lindlar's
Problem 13 of 14
Structure of
A
1. NaNH2
Submit
2.
CH3CH₂Br
Structure of
product D
Chapter 22 Solutions
EBK ORGANIC CHEMISTRY
Ch. 22 - Prob. 22.1PCh. 22 - Prob. 22.2PCh. 22 - Prob. 22.3PCh. 22 - Prob. 22.4PCh. 22 - Prob. 22.5PCh. 22 - Prob. 22.6PCh. 22 - Prob. 22.7PCh. 22 - Prob. 22.8PCh. 22 - Prob. 22.9PCh. 22 - Prob. 22.10P
Ch. 22 - Prob. 22.11PCh. 22 - Prob. 22.12PCh. 22 - Prob. 22.13PCh. 22 - Prob. 22.14PCh. 22 - Prob. 22.15PCh. 22 - Prob. 22.16PCh. 22 - Prob. 22.17PCh. 22 - Prob. 22.18PCh. 22 - Prob. 22.19PCh. 22 - Prob. 22.20PCh. 22 - Prob. 22.21PCh. 22 - Prob. 22.22PCh. 22 - Prob. 22.23PCh. 22 - Prob. 22.24PCh. 22 - Prob. 22.25PCh. 22 - Prob. 22.26PCh. 22 - Prob. 22.27PCh. 22 - Prob. 22.28PCh. 22 - Prob. 22.29PCh. 22 - Prob. 22.30PCh. 22 - Prob. 22.31PCh. 22 - Prob. 22.32PCh. 22 - Prob. 22.33PCh. 22 - Prob. 22.34PCh. 22 - Prob. 22.35PCh. 22 - Prob. 22.36PCh. 22 - Prob. 22.37PCh. 22 - Prob. 22.38PCh. 22 - Prob. 22.39PCh. 22 - Prob. 22.40PCh. 22 - Prob. 22.41PCh. 22 - Prob. 22.42PCh. 22 - Prob. 22.43PCh. 22 - Prob. 22.44PCh. 22 - Prob. 22.45PCh. 22 - Prob. 22.46PCh. 22 - Prob. 22.47PCh. 22 - Prob. 22.48PCh. 22 - Prob. 22.49PCh. 22 - Prob. 22.50PCh. 22 - Prob. 22.51PCh. 22 - Prob. 22.52PCh. 22 - Prob. 22.53PCh. 22 - Prob. 22.54PCh. 22 - Prob. 22.55APCh. 22 - Prob. 22.56APCh. 22 - Prob. 22.57APCh. 22 - Prob. 22.58APCh. 22 - Prob. 22.59APCh. 22 - Prob. 22.60APCh. 22 - Prob. 22.61APCh. 22 - Prob. 22.62APCh. 22 - Prob. 22.63APCh. 22 - Prob. 22.64APCh. 22 - Prob. 22.65APCh. 22 - Prob. 22.66APCh. 22 - Prob. 22.67APCh. 22 - Prob. 22.68APCh. 22 - Prob. 22.69APCh. 22 - Prob. 22.70APCh. 22 - Prob. 22.71APCh. 22 - Prob. 22.72APCh. 22 - Prob. 22.73APCh. 22 - Prob. 22.74APCh. 22 - Prob. 22.75APCh. 22 - Prob. 22.76APCh. 22 - Prob. 22.77APCh. 22 - Prob. 22.78APCh. 22 - Prob. 22.79APCh. 22 - Prob. 22.80APCh. 22 - Prob. 22.81APCh. 22 - Prob. 22.82APCh. 22 - Prob. 22.83APCh. 22 - Prob. 22.84APCh. 22 - Prob. 22.85APCh. 22 - Prob. 22.86APCh. 22 - Prob. 22.87APCh. 22 - Prob. 22.88APCh. 22 - Prob. 22.89APCh. 22 - Prob. 22.90APCh. 22 - Prob. 22.91APCh. 22 - Prob. 22.92APCh. 22 - Prob. 22.93APCh. 22 - Prob. 22.94APCh. 22 - Prob. 22.95APCh. 22 - Prob. 22.96APCh. 22 - Prob. 22.97APCh. 22 - Prob. 22.98AP
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
- Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forwardDraw structural formulas for (1) the alkyltriphenylphosphonium salt formed by treatment of each haloalkane with triphenylphosphine, (2) the phosphonium ylide formed by treatment of each phosphonium salt with butyllithium, and (3) the alkene formed by treatment of each phosphonium ylide with acetone.arrow_forwardHydrocarbon A has the formula C9H12 and absorbs 3 equivalents of H2 to yield B, C9H18, when hydrogenated over a Pd/C catalyst. On treatment of A with aqueous H₂SO4 in the presence of mercury(II), two isomeric ketones, C and D, are produced. Oxidation of A with O3 gives a mixture of acetaldehyde (CH3COH) and the trialdehyde shown below. Propose structures for compounds A-D. CH,CHO OCHCH,CHCH CHOarrow_forward
- Write a mechanism that accounts for the formation of ethyl isopropyl ether as one of the products in the following reaction. CI OEt HCI EtOH Write the mechanism for step one of this reaction. Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. Write the mechanism for step two of this reaction (where the product of step one reacts with the solvent, ethanol). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. Write the mechanism for the last step of this reaction (formation of ethyl isopropyl ether). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. CI will act as the base in this reaction.arrow_forwardIsoerythrogenic acid, C18H26O2, is an acetylic fatty acid that turns a vivid blue on exposure to UV light. On Catalytic hydrogenation over a palladium catalyst, five molar equivalents of hydrogen are absorbed, and stearic acid, CH3(CH2)16CO2H, is produced. Ozonolysis of isoerythrogenic acid yields the following products: formaldehyde, CH2O, malonic acid, HO2CCH2CO2H, adipic acid, HO2C(CH2)4CO2H, and the aldehyde carboxylic acid, OHC(CH2)6CO2H. Provide a structure for isoerythrogenic acid.arrow_forwardPropanal and propanone react in a similar way with acidified aqueous potassium cyanide, KCN. For this reaction to occur reasonably quickly, the pH of the solution should be approximately 4. The reaction of propanal proceeds with acidified potassium cyanide proceeds more rapidly than that of propanone. Referring to the mechanism of the reactions, explain this phenomenon.arrow_forward
- Consider the monosubstituted benzene reagent X. Nitration of X yields product Y. Product Y is analysed by 1H and 13C NMR spectroscopy (see Figures 1 to 4). Determine the structure of X and Y on the basis of the spectral data provided.arrow_forwardDehydration of 2,2,3,4,4,-pentamethyl-3-pentanol gives two alkenes A and B. Ozonolysis of A gives formaldehyde and 2,2,4,4-tetramethyl-3- pentanone. Ozonolysis of B gave formaldehyde and 3,3,4,4-tetramethyl-2-pentanone. Identify and draw the structures of A and B, and explain how B could be formed in the dehydration reaction.arrow_forwardThe sex attractant of the housefly has the formula C23H46. When treated with warm potassium permanganate, this pheromone gives two products: CH3(CH2)12COOH and CH3(CH2)7COOH. Suggest a structure for this sex attractant. Explainwhich part of the structure is uncertainarrow_forward
- 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*arrow_forwardPentane-2,4- dione reacts with NaOH to give H2O and sodium salt of a carbaion. write a complete structural formula for the carbanion and use resonance forms to show stabilization of the carbanion.arrow_forwardTreatment of a hydrocarbon A (molecular formula C9H18) with Br2 in the presence of light forms alkyl halides B and C, both having molecular formula C9H17Br. Reaction of either B or C with KOC(CH3)3 forms compound D (C9H16) as the major product. Ozonolysis of D forms cyclohexanone and acetone. Identify the structures of A–D.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
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