EBK ORGANIC CHEMISTRY-PRINT COMPANION (
4th Edition
ISBN: 9781119776741
Author: Klein
Publisher: WILEY CONS
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Question
Chapter 6, Problem 61IP
(a)
Interpretation Introduction
Interpretation:
The curved arrows for each step of the mechanism must be drawn and the sequence of arrow pushing patterns must be identified.
Concept Introduction :
The curved arrow shows the electron flow; and thereby, it shows bond breaking and new bond formation. The alpha hydrogen of
(b)
Interpretation Introduction
Interpretation:
For the conversion of 4 to 5 the electrophilic and nucleophilic centers must be identified with the help of resonance.
Concept Introduction :
Electrophilic centers are those where there is low electron density. Nucleophilic centers are those where there is higher electron density.
(c)
Interpretation Introduction
Interpretation:
Configuration of the newly formed chiral center during conversion of 4 to 5 must be determined. Why the other possible configuration is not observed must be explained.
Concept Introduction :
The configuration of a chiral center depends on the three dimensional orientations and priorities of different groups. Priorities of those groups can be determined using CIP (Cahn-Ingold-Prelog) priority rules according to which higher is the
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
An organic compound A (C2H3N) is used as a solvent of choice for many organic reactions because it is not reactive in mild acidic and basic conditions. Compound A on treatment with Ni/ H2 forms B. When B is treated with nitrous acid at 273K ethanol is obtained. When B is warmed with chloroform and NaOH a foul smelling compound C formed. Identify A, B and C.
Synthesis. Developments in medicine follows advances in synthetic
chemistry. Anyone that disagrees would perhaps be well served to
imagine the state of surgery if organic chemists had not developed local
anesthetics. The following structure is the free base of hexylcaine (1), a
local anesthetic developed by Merck. Propose a synthesis of 1 starting
(1)
from benzene and acyclic components containing five carbons or less. Justify any chemo-, regio- or
stereo selective steps in your synthesis. (
5) Limonene is a compound found in orange oil and lemon oil with molecular formula C₁0H16-
When limonene is treated with 1 equivalent of mCPBA, the product is limonene oxide as depicted
below. When limonene is treated with excess ozone (03) and then with dimethylsulfide (Me₂S),
one of the organic products of the reaction is formaldehyde. Of the structures below, which
correspond to the structure of limonene and/or the structure of the other major organic product
when limonene is reacted with O3 and Me₂S? Please select any and all that apply.
A)
'Н
H
B)
?
H
1) 03 (XS)
2) Me₂S (xs)
?
limonene, C10H16
D)
mCPBA
(1 equiv)
E)
limonene
oxide
None of
the
above
Chapter 6 Solutions
EBK ORGANIC CHEMISTRY-PRINT COMPANION (
Ch. 6.1 - Prob. 1LTSCh. 6.1 - Prob. 1PTSCh. 6.1 - Prob. 2ATSCh. 6.2 - Prob. 3CCCh. 6.3 - Prob. 4CCCh. 6.3 - Prob. 5CCCh. 6.4 - Prob. 6CCCh. 6.6 - Prob. 7CCCh. 6.7 - Prob. 2LTSCh. 6.7 - Prob. 8PTS
Ch. 6.7 - Prob. 9PTSCh. 6.7 - Prob. 10ATSCh. 6.8 - Prob. 3LTSCh. 6.8 - Prob. 11PTSCh. 6.8 - Prob. 12ATSCh. 6.9 - Prob. 4LTSCh. 6.9 - Prob. 13PTSCh. 6.9 - Prob. 14ATSCh. 6.10 - Prob. 5LTSCh. 6.10 - Prob. 15PTSCh. 6.10 - Prob. 16ATSCh. 6.11 - Prob. 6LTSCh. 6.11 - Prob. 17PTSCh. 6.11 - Prob. 18ATSCh. 6 - Prob. 19PPCh. 6 - Prob. 20PPCh. 6 - Prob. 21PPCh. 6 - Prob. 22PPCh. 6 - Prob. 24PPCh. 6 - Prob. 25PPCh. 6 - Prob. 26PPCh. 6 - Prob. 27PPCh. 6 - Prob. 28PPCh. 6 - Prob. 29PPCh. 6 - Prob. 30PPCh. 6 - Prob. 31PPCh. 6 - Prob. 32PPCh. 6 - Prob. 33PPCh. 6 - Prob. 34PPCh. 6 - Prob. 35PPCh. 6 - Prob. 36PPCh. 6 - Prob. 37PPCh. 6 - Prob. 38PPCh. 6 - Prob. 39PPCh. 6 - Prob. 40PPCh. 6 - Prob. 41PPCh. 6 - Prob. 43ASPCh. 6 - Prob. 44ASPCh. 6 - Prob. 45ASPCh. 6 - Prob. 46ASPCh. 6 - Prob. 47ASPCh. 6 - Prob. 48ASPCh. 6 - Prob. 49ASPCh. 6 - Prob. 50IPCh. 6 - Prob. 51IPCh. 6 - Prob. 52IPCh. 6 - Prob. 53IPCh. 6 - Prob. 54IPCh. 6 - Prob. 55IPCh. 6 - Prob. 56IPCh. 6 - Prob. 57IPCh. 6 - Prob. 58IPCh. 6 - Prob. 59IPCh. 6 - Prob. 60IPCh. 6 - Prob. 61IPCh. 6 - Prob. 62CPCh. 6 - Prob. 64CP
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
- The standard procedure for synthesizing a compound is the stepwise progress toward a target molecule by forming individual bonds through single reactions. Typically, the product of each reaction is isolated and purified before the next reaction in the sequence is carried out. One of the ways nature avoids this tedious practice of isolation and purification is by the use of a domino sequence in which each new product is built on a preexisting one in stepwise fashion. A great example of a laboratory domino reaction is William S. Johnsons elegant synthesis of the female hormone progesterone. Johnson first constructed the polyunsaturated monocyclic 3 alcohol (A) and then, in an acid-induced domino reaction, formed compound B, which he then converted to progesterone. A remarkable feature of this synthesis is that compound A, which has only one stereo-center, gives compound B, which has five stereocenters, each with the same configuration as those in progesterone. We will return to the chemistry of Step 2 in Section 16.7 and to the chemistry of Steps 3 and 4 in Chapter 19. In this problem, we focus on Step 1. (a) Assume that the domino reaction in Step 1 is initiated by protonation of the 3 alcohol in compound A followed by loss of H2O to give a 3 carbocation. Show how the series of reactions initiated by the formation of this cation gives compound B. (b) If you have access to a large enough set of molecular models or to a computer modeling program, build a model of progesterone and describe the conformation of each ring. There are two methyl groups and three hydrogen atoms at the set of ring junctions in progesterone. Which of these five groups occupies an equatorial position? Which occupies an axial position?arrow_forwardAlcohols are important for organic synthesis, especially in situations involving alkenes. The alcohol might be the desired product, or the OH group might be transformed into another functional group via halogenation, oxidation, or perhaps conversion to a sulfonic ester derivative. Formation of an alcohol from an alkene is particularly powerful because conditions can be chosen to produce either the Markovnikov or non-Markovnikov product from an unsymmetrical alkene. Using your reaction roadmap as a guide, show how to convert 4-methyl-1-pentene into 5-methylhexanenitrile. You must use 4-methyl-1-pentene and sodium cyanide as the source of all carbon atoms in the target molecule. Show all reagents needed and all molecules synthesized along the way.arrow_forward3. It is required to introduce a halogen group to a five membered ring, thiophene. Discuss the reaction mechanism involved in the reaction by selecting a suitable halogen group and analyze why a particular substituted product obtained after the reaction is predominant over the other possible product(s) with the help of reactions. To meet the ever increasing demand of global population, the demand for textile products and consumption of dyes by these industries is increasing.arrow_forward
- 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.arrow_forward10. M and N are amines with the molecular formula C3H»N. Reaction of M with sodium nitrite and HCI releases nitrogen gas and produces a mixture of X and Y and Propanol while N produces a yellowish oily compound, S when reacted with the same reagents. Give the structures of M, N, X, Y, and S. Outline the synthesis of M from a suitable alkene.arrow_forward(c) The structures of lycopene, beta-carotene and retinol are shown below. Lycopene Beta-carotene H3C CH; CH3 CH3 OH Retinol (vitamin A) CH3 Using appropriate reaction mechanisms: (i) Show how lycopene is converted into beta-carotene. (ii) Briefly explain how retinol is formed from beta-carotene.arrow_forward
- (+)-Aureol is a natural product that shows selective anticancer activity against certain strains of lung cancer and colon cancer. A key step in the biosynthesis of (+)-aureol (how nature makes the molecule) is believed to involve the conversion of carbocation A to carbocation B (Org. Lett. 2012, 14, 4710-4713). HO. 6.60a H₂C A НО CH3 CH3 Draw curved arrows on the first two structures provided to depict a possible mechanism for the conversion of A to B via the intermediate shown. H OH CH₂ HO OH H₂C B H₂C CH₂ НО H OH CH3 OH H₂C CH₂ НО. CH3 CH3 OHarrow_forward2,4-D is a synthetic auxin (a plant hormone) used in the control of broadleaf weeds, and one of the most widely used herbicides in the world. It is produced commercially by the following reaction: chloroacetic acid + dichlorophenol → hydrochloric acid + 2,4-D C2H3ClO2 + C6H4Cl2O → HCl + C8H6Cl2O3 How much chloroacetic acid does it take to manufacture 5.18 grams of 2,4-D?arrow_forward(10pts) Compound A, C10H16, was found to be optically active. On catalytic reduction over a palladium catalyst, 2 equivalents of hydrogen were absorbed, yielding compound B, CioH2o. On ozonolysis of A, two fragments were obtained. One fragment was identified as acetic acid (CHCOOH). The other fragment, compound C, was an optically active carboxylic acid, C8H14O2. Write reactions, and draw the correct structures for A-C, explain your answer in detail.arrow_forward
- (a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) (1) 1 Ph THF A Ph Ph B H₂SO4 100 °C 3 OH What is the name of the reaction that is followed by reaction Method A?arrow_forwardOrganotin compounds play a significant role in diverse industrial applications. They have been used as plastic stabilizers and as pesticides or fungicides.One method used to prepare simple tetraalkylstannanes is the controlled direct reaction of liquid tin(IV) chloride with highly reactive trialkylaluminum compounds, such as liquid triethylaluminum (Al(C2H5)3). 3SnCl4 + 4Al(C2H5)3 3Sn(C2H5)4 + 4AlCl3 In one experiment, 0.230 L of SnCl4 (d = 2.226 g/mL) was treated with 0.396 L of triethylaluminum (Al(C2H5)3); d = 0.835 g/mL). If 0.335 L of tetraethylstannane (d = 1.187 g/mL) were actually isolated in this experiment, what was the percent yield?arrow_forward1. There are several isomeric alkanes of molecular formula C6H14.Two of these exhibit the following 1H-NMR spectra. Propose a structure for each of the isomers. Isomer A: δ = 0.84 (d, 12 H), 1.39 (septet, 2H) ppm Isomer B: δ = 0.84 (t, 3 H), 0.86 (s, 9H), 1.22 (q, 2H) ppmarrow_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
IR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=_TmevMf-Zgs;License: Standard YouTube License, CC-BY