Given the information pictured,The final step of the reaction sequence uses PhLi. Provide a reason and possible mechanism by which this final elimination and hydrolysis reaction would occur. 1,2-Trans-cyclohexanediol has been shown to be an efficient support for the asymmetriccyclopropanation of allylic ethers as shown in the scheme below.PhPh Et₂Zn + CICH₂lanToluene3 h, -20°COHOHBUNI CH₂Cl₂Tf₂OPhOA÷αPhLi+HOTHF-100°CPh

Answered: Image /qna-images/answer/00e21692-74ee-4220-a2b3-5c810399595b.jpg

Answered: clopropanation of allylic ethers as…

clopropanation of allylic ethers as shown in the scheme below. Ph Et₂Zn + CICH₂l Toluene 3 h, -20°C 'OH Ph and = PhLi + НО. THF -100°C BUNI Tf₂O OH CH₂Cl₂ Ph

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter8: Haloalkanes, Halogenation, And Radical Reactions

Section: Chapter Questions

Problem 8.11P

See similar textbooks

Related questions

Q: 4. Write the product and the mechanism for reaction. Write the names of starting material and…

Q: 2X₂Y3 = 2X₂ + 3Y₂ Keq = 4 x 10° The initial concentration of the reactant is 2 M. Calculate its…

A: The given equilibrium reaction is 2X2Y3 ⇌ 2X2 + 3Y2(g); Keq = 4 × 108 The…

Q: The first step in the catabolism of most amino acids is the removal of the nitrogen atom by transfer…

A: Organic reactions are those in which organic reactant react to form organic products.

Q: What is the final temperature of gold. The specific heat capacity is 0.128 j/g. C

A: Specific heat capacity is amount of heat required to raise temperature of one gram of a substance by…

Q: 9. It has been said that seawater contains more gold than all of the world's banks. One estimate of…

Q: Consider the following reaction 2 HI(g) ⇌ H2(g) + I2(g); Kp = 0.016 If 0.820 atm HI(g) is sealed…

A: Given reaction: 2 HI(g) ⇌ H2(g) + I2(g) Kp = 0.016 The initial partial pressure of HI(g) = 0.820…

Q: 1. 2. H₂C Aqueous ethanol + HBr H CH₂ + Proton transfer d =E1 Elimination f SN1 Nucleophilic…

Q: an 7. Suggest observations: explanation for the following .a) The dipole moment of the hydrocarbon…

Q: qu. a) NaOH, H₂O HEAT b) work-up a) NaOCH₂CH3 ethanol b) work-up a) NaOCH3, solvent b) work-up G

A: Detail mechanistic explanation is given below

Q: The rate constant k for a certain reaction is measured at two different temperatures: temperature k…

Q: Please provide the POINT GROUPS of the following objects and explain why.

Q: 5. You admit an approximately 4 week old kitten to the hospital for treatment of failure to thrive.…

A: Given that, The concentration of the stock solution is S1 = 50%. The concentration of the dilute…

Q: Nitrous acid is a weak acid and has a concentration of 0.65 mol/L. What is the pH of the solution…

Q: hond How many form from are needed to prepare 1.5 L af 9 1.8m eahpoy Solution ?

A: Molarity is a concentration term for a solution. The molarity of the given solution is defined as…

Q: Carbon dioxide in high levels can cause death. One method of removing carbon dioxide from the air of…

A: Since you have asked multiple question, we will solve the first question for you.If you want any…

Q: IE₁ = 1012 kJ/mol; IE2 = 1900 kJ/mol; IE3 = 2910 kJ/mol; IE4 = 4960 kJ/mol; IE5 = 6270 kJ/mol; IE6 =…

Q: one liter of a 5.0% solution of NaCl. b. 10 liters of a 6.0 M NaOH solution. (MM of NaOH is 40.00…

A: The explanation is given below-

Q: Identify the chemical type of each compound (2a to 2c), according to the options given in the Answer…

A: As per the bartleby expert guidelines, I am allowed to answer FIRST one question at a time. Please…

Q: The equilibrium constant, Ke, for the reaction N2O4 (g) 2NO2(g) is 4.8 x 10-3 If the equilibrium…

Q: The electron in a Bohr hydrogen atom is bound less tightly when it has a quantum number of 3 than…

Q: a general chemistry student measured the pH of a 0.510 M aqueous solution of nitrous acid to be…

A: Here we are required to find the dissociation constant for weak acid nitrous acid

Q: Question #2 Given a density of 1.836 g/mL and a mass percent of H₂SO4 of 96.00 %, The molar mass of…

A: Given,Density of H2SO4 = 1.836 g/mLMass percentage of H2SO4 = 96.00 % Volume of solution = 1.00…

Q: Which of the arrows points to an atom that is 30 (tertiary) and sp³ hybridized? с d a mamana www

Q: Ethanol vapours were allowed to completely fill a jug with a volume of 18.9L. The ethanol was burned…

Q: 50 ppm .00 ppm 50 ppm 100

A: The solution is given below -

Q: A student takes a 25.0 mL volume from a stock solution of 1.14 mol L-1 magnesium chloride. How many…

Q: 1. Which of the following catalyst best describes when the catalyst and the reactant(s) are in…

A: Since you have asked multiple question, we will solve the first question for you. If you want any…

Q: Br 1. Mg, Et₂0 2. CH2O 3. PDC 36 CHO 1. n-HexMgBr 2. PDC m 34; 68% yield

A: PCC and PDC are mild oxidizing agent used to prevent the over oxidation of alcohol to acid .

Q: What is the oxidation state on the central carbon in the following compound? H₂C-CH

Q: Chemistry Adam generated oxygen gas in the thermal decomposition of potassium chlorate. At 24°C and…

Q: c. the concentration of the reactants to the rate of the reaction d. the concentration of the…

A: 18.A chemical reaction rate compares a. the temperature of the reactants to the rate of the reaction…

Q: A hydrogen gas with a volume of 8.98 L is collected at 38.8 °C. Find the volume the gas will occupy…

Q: (8.2)Which of the following occurs as the wavelength of a photon increases? O None of the above…

A: Energy of photon = E = hc/ wavelength E = h × frequency h = plank constant

Q: The Ottawa Charter is increasingly used to guide the development of health promotion activities in…

A: The very first international conference on health promotion was held on Ottawa on 1st November,…

Q: Briefly explain the reasons for the use of the following techniques in this experiment. a. The…

Q: (9.6) Which of the following is in the correct order of increasing atomic radius? O Cs > S > Si Cs >…

A: Atomic radius: The distance between the nucleus and the outermost electron is known as the atomic…

Q: If you start with 20 mM acetic acid, 50 mM acetate (pKa = 4.76) solution, how much of a 0.15 M…

Q: nuclear equation for the positron emission from the Thallium-201 radioisotope.

A: Positron emssion or beta plus decay is subtype of radioactive decay in which a proton inside…

Q: MISSED THIS? Watch KCV 15.8. WE 15.12: Read Section 15.8. You can click on the Review link to access…

Q: What is the concentration of the following solution? 275g of KNO3 in 1250mL of water?

Q: Draw structural formulas for the alkoxide ion and the alkyl(aryl) bromide that may be used in a…

A: Here we are required to find the Starting material for the synthesis of ether.

Q: arch projec e a compara mical equat

A: Inert atmosphere will be created using nitrogen or helium.

Q: 1. Write the product, side products and the mechanism for reaction. Write the names of starting…

Q: Balance the following chemical equation by providing the correct coefficients. [2](NH4)3PO4 +…

Q: The rate constant of a certain reaction is known to obey the Arrhenius equation, and to have an…

Q: Draw a skeletal ("line") structure of this molecule: || O CH3 0 | || CH3-C-N-C-CH₂-CH3 Click and…

A: The structure is shown below.

Q: What is the molar mass (in kg/mol) of carbon tetrachloride (CC14)? 6 17 C CL 35.45 12.01 2. 0.2535…

A: Here we are required to find the molar mass of carbon tetrachloride

Q: 1. Write the product, side products and the mechanism for reaction. Write the names of starting…

Q: ▼ ▼ Part A In order understand how this equation derived and why it holds true, the product f each…

A: Part A) Given, Concentration of the solution (M1) = 0.687 M = 0.687 mol/L Volume of the solution…

Q: 60 mL of a 0.4M solution of the histidine is adjusted to pH = 2.68 (partially protonated). The…

Concept explainers

Diol

In chemistry there are so many chemical compounds that have a hydroxyl group but a chemical compound having two hydroxyl groups (-OH) is termed as a diol. It also implies the presence of two alcohols whereas polyols contain two or more than two hydroxyl groups (-OH). Glycol or 1,2-diol is an aliphatic diol that has two alcohol groups on adjacent carbon atoms. In industries, the most commonly used diol is ethylene glycol.

Question

100%

Given the information pictured,

The final step of the reaction sequence uses PhLi.

Provide a reason and possible mechanism by which this final elimination and hydrolysis reaction would occur.

1,2-Trans-cyclohexanediol has been shown to be an efficient support for the asymmetric
cyclopropanation of allylic ethers as shown in the scheme below.
Ph
Ph Et₂Zn + CICH₂l
an
Toluene
3 h, -20°C
OH
OH
BUNI CH₂Cl₂
Tf₂O
Ph
OA÷α
PhLi
+
HO
THF
-100°C
Ph

Expert Solution

This question has been solved!

Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.

SEE SOLUTION Check out a sample Q&A here

Step 1

VIEW

Step 2

VIEW

Step by step

Solved in 2 steps with 2 images

SEE SOLUTION Check out a sample Q&A here

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

When cis-2-decalone is dissolved in ether containing a trace of HCl, an equilibrium is established with trans-2-decalone. The latter ketone predominates in the equilibrium mixture. Propose a mechanism for this isomerization and account for the fact that the trans isomer predominates at equilibrium.
Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.
IQ3 نقطة واحدة Name the following heterocyclic ethers (a) إجابتك نقطة واحدة Name the following heterocyclic ethers H. CH,CH3 (d) CH,CH, H. إجابتك نقطة واحدة Name the following heterocyclic ethers -CH3 CH; () Br إجابتك. II >
: Treatment of (CHa)CHCH(OH)CH,CH3 with TSOH affords two products (M and N) with molecular formula CgH12. The 'H NMR spectra of M and N are given below. Propose structures for M and N and draw a mechanism to explain their formation. 1H NMR of M 3H 1H NMR of N 3H 3H 3 H 1H 3 H 2 H 2H 2H 8 7 6 4 1 0 9 8. 2 1 ppm ppm 4.
Reaction of (CH3)3CCHO with (C6H5)3P=C(CH3)OCH3, followed by treatment with aqueous acid, affords R (C7H14O). R has a strong absorption in its IR spectrum at 1717 cm−1 and three singlets in its 1H NMR spectrum at 1.02 (9 H), 2.13 (3 H), and 2.33 (2 H) ppm. What is the structure of R? We will learn about this reaction in Chapter 18.
An unknown compound has a molecular formula of C4H6O2. Its IR spectrum shows absorptions at 3095, 1762, 1254, and 1118 cm -1. It exhibits the following signals in its 1H NMR spectrum (ppm): 2.12 (singlet,3H), 4.55 (doublets of doublets, 1H), 4.85 (doublet of doublets, 1H), 7.25 (doublets of doublets, 1H); and the following signals in its 13C NMR spectrum (ppm): 20.8, 100.4, 141.2, 168.0. Draw the structure of the unknown compound
1) In the following reactions, give the nature and possibly the stereochemistry of A1, A2 and B and justify the proportions obtained. 4 1=3 |=1 CI ull OH KOtBu 3 DMSO H₂SO4 majority A1 A1 + 2)When the first compound is treated with MeONa in methanol, compounds A1 and B are also obtained, as well as a higher molecular weight compound C, which has a higher molecular weight. B are also obtained as well as a higher molecular weight compound C whose 1H NMR spectrum is given below. Justify the formation of C. 2 PPM equimolar mixture + isomere of A1 1=3 mobilie B A2 1=3 1=3 1 1=3 O
Reaction of p-cresol with two equivalents of 2-methylprop-1-ene affords BHT, a preservative with molecular formula C15H24O. BHT gives the following 1H NMR spectral data: 1.4 (singlet, 18 H), 2.27 (singlet, 3 H), 5.0 (singlet, 1 H), and 7.0 (singlet, 2 H) ppm. What is the structure of BHT? Draw a stepwise mechanism illustrating how it is formed.
Treatment of cis-4-bromocyclohexanol with HO− affords compound Aand cyclohex-3-en-1-ol. Treatment of trans-4-bromocyclohexanol under the same conditions forms compound B and cyclohex-3-en-1-ol. A and Bcontain different functional groups and are not isomers of each other.Propose structures for A and B and offer an explanation for theirformation.
An unknown compound has a molecular formula of C,H,O. Its IR spectrum shows prominent absorptions at 2980, 2960, and 1718 cm . It exhibits the following signals in its H NMR spectrum (ppm): 1.06 (triplet, 3H), 2.12 (singlet, 3H), 2.45 (quartet, 2H); and the following signals in its ¹3C NMR spectrum ( ppm): 7.6, 29.5, 36.8, 208.8. Draw the structure of the unknown compound. Click and drag to start drawing a structure. 0 X 0:0
For following substituted benzenes: [1] C6H5Br; [2] C6H5CN; [3] C6H5OCOCH3: Does the substituent activate or deactivate the benzene ring inelectrophilic aromatic substitution?
9a) The proton bonded to the carbon adjacent to the carbonyl group in the following compound can be classified into which chemical shift in the ¹H-NMR spectra of aldehydes and ketones? R or H H - 10.0-12.0 ppm R H -2.0-3.0 ppm NO₂ N (1) 9b) Choose the one below that could be resolved into enantiomers. (1) alpha hydrogens = ? ppm NO₂ NO₂ 9c) Which of the following is the major product of the reaction below. `N H -5.0-7.0 ppm (11) (11) -0.0-1.0 ppm HNO3, H₂SO4 H NO₂ (III) NO₂ (1) and (II) (IV) None of the options (IV)