4. Reactivity. Propose a mechanism for each of the following transformations toexplain the observed regioselectivity and stereochemistry.a.-COCISiMe3AICI3Mé`Me76%b.Me(Ph;P)4Pd (cat.)CO-MeEtzN, CH3CN, refluxMeMeO2C80%с.MeMeSiMe3n-BugNFDMF, HMPA69%d.EtAICI (2 eq)toluene-SiMe385%

Answered: 4. Reactivity. Propose a mechanism for…

4. Reactivity. Propose a mechanism for each of the following transformations to explain the observed regioselectivity and stereochemistry. a. -COCI SiMe3 AICla CH2Cl2 Me Me 76%

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter19: Eas: Electrophilic Aromatic Substitution

Section: Chapter Questions

Problem 45E

See similar textbooks

Related questions

Q: Question 1 What synthetic goal is achieved by subjecting an alkene to an…

Q: A 2 dm3 flask maintained at 700 K contains 0.1 mol of CO(g) and a catalyst for the reaction CO(g) +…

A: Recall the given equation, CO g + 2 H2 g → CH3OH g2 dm3 flask contains 0.1 mole of CO…

Q: Which of the following carbonyl compounds will NOT undergo Aldol addition reactions when treated…

Q: For the following reaction situation, select a correct product characterization using the response…

Q: Band theory uses molecular orbital theory to describe the bonding in metals and other solids.…

A: Conductors are substances that are good conductor of heat and electricity. Insulator is material…

Q: 1 Draw the major organic product of this first step in Box 2.

A: In sulphonation reaction, there is reaction of phenol with concentrated sulphuric acid.

Q: What is the charge of the predominant form of phosphoric acid at pH=3.00 pKa 2.15, pKa27.20, pK=…

A: Given: pH = 3.00

Q: NaOEt H. AICI; CI NaOMe

A: Since, you have multiple subparts questions so i will solved first three subparts for you and rest…

Q: Which of the following experiments would be consistent with this mechanism? Step 1: 2NO2(g) → NO3(g)…

Q: Given the reaction: 2Fe(s) + 3C12(g) --> 2FECI3(s) What is the oxidation state of the product iron?…

A: What is the oxidation state of Fe in FeCl3 ?

Q: Write the chemical formula of the following complex ions. formula name tetraaquacobalt(III)…

A: The chemical formula of the above compounds are given below

Q: mportant values if needed for this question. The decomposition of dinitrogen pentoxide in carbon…

Q: Zn(s) | Ag*(aq) || Zn²* (aq) | Ag(s) Ag(s) | Ag* (aq) || Zn2+ (aq) | Zn(s) Ag(s) | Zn* (aq) || Ag*…

A: In electrochemical cell, Anode half reaction is written left side and cathode half reaction is…

Q: For a particular redox reaction, CrCr is oxidized to CrO2−4CrO42− and Cu2+Cu2+ is reduced to Cu+Cu+.…

A: Cr is oxidized to CrO42- and Cu2+ is reduced to Cu+. Cr + Cu2+ → CrO42- +…

Q: A compound of molecular formula C5H10O forms a yellow precipitate with 2,4-dinitrophenylhydrazine…

Q: Question 37 Provide the reagents necessary to complete the following transformation. CH2CH CH,CH…

A: One of the most common ways of epoxidation is the addition of an oxygen atom to an alkene with…

Q: Question 2 Consider the substitution reaction shown below. By what mechanism will the reaction…

Q: The melting point of calcium is 851 C, it's solid-state specific heat (Csolid) is 0.632 J/gC, and…

A: a.) At melting point , there would be only phase change from solid to liquid. So energy required to…

Q: how the step(s) necessary to tran cht. (CH3),CCH¿CH

A: Question 01: According to the question, we need to convert 3,3-dimethyl butanal to 3,3-dimethyl…

Q: 1 ppm 1. Determine the minimum number of hydrogens present in the compound? 2. If the compound has…

Q: Determine the concentration in molarity of 100ml acid solution used in titrating a 67.119g of sodium…

A: Sodium hydroxide, NaOH is a monoacidic base and KHP is a monoprotic acid. Balanced neutralization…

Q: Ina calorimetry experiment a student determines the enthalpy for the reaction of magnesiam with…

A: Given: The enthalpy of reaction determined in the experiment is -430 KJ/mol while the true enthalpy…

Q: Given the reaction: 2Fe(s) + 3C12(g) --> 2FEC13(s) Write the half reaction showing reduction.

A: Reduction is the process of gain of electron. And oxidation is the process of loss of electron. To…

Q: Question 18 In GC experiment, a standard solution containing 0.147 grams ethanol gave a peak area of…

Q: Use the PEC diagram given below for copper (II) sulfate to select the correct analysis of solubility…

A: Here from the PEC diagram of solubility of CuSO4 in water ,we have to predict the correct statement.

Q: Provide a detailed arrow-pushing mechanism for the following transformation: Me PHOH PhO. Et Мe Me…

Q: A. Draw a reaction coordinate diagram that is consistent with the shown chemical equations and…

A: Hii there, As there are multiple question posted. we are answering first question. If you need…

Q: You are asked to determine the alkali present and the percentage of each in a component of a sample…

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

Q: a. Provide one similarity between an SN1 and an SN2 reaction mechanism. b. Draw a fully labelled,…

A: Nucleophilic substitution reactions are defined as reactions in which one nucleophile is replaced by…

Q: What is the molarity of a sodium chloride solution (MP = 58.5 g/mol) if 23.4 g of this substance…

A: Molarity of solution is defined as number of moles of solute dissolved per litre of solution.

Q: Find the type of reaction, enthalpy, entropy, and spontaneous (- Delta G) of all three problems.

A: The reactions given are, 1) 2) 3)

Q: What is the maximum amount of iron, in grams, that can be gotten out of 43.91 grams of Fe2O3? Enter…

Q: 6. Arrange the following 0.01 M substances in order of increasing pH. HNO3: pK, = -1.38 HNO2: pka =…

Q: 1. Consider the following absorbance spectra of two molecules. Which molecule electromagnetic…

A: The absorbance spectra of the molecules given are,

Q: A galvanic cell Cr(s)|Cr2+(aq) || Sn2+(aq)|Sn(s) is constructed using a completely immersed Cr…

A: Cr(s) is undergoing oxidation to Cr2+(aq) and Sn2+(aq) undergoing reduction to Sn(s) half-reactions…

Q: Calculate the pH of a 0.654 M solution of an acid with Ka = 2.33 x 10-5.

Q: How many degrees of unsaturation are present in the following molecules: ii i iv HO C10H22 C,H;CI

A: Degrees of unsaturation (D.U) :- The total number of pi bonds and cyclic rings present in a…

Q: the box next to each molecule on the right that has the shape molecules model (check all that apply)…

A: Here V-shape molecular structure given.

Q: Calculate the change in energy, in kilojoules per mole, for the transmutation of radium from the…

A: Change in energy for a nuclear reaction is cakx using formula ∆E = ∆m × c2 ∆m is change in mass c…

Q: For the following reaction, select a correct product characterization from the response list. Ni…

A: Which one of the following is correct answer

Q: Fill in the table. Element Number of Protons Number of Neutrons Number of Electrons Mass Number…

A: Fill in the blanks--

Q: Question 26 If a reaction is endothermic, then O AH° 0 O AS° > 0

Q: 3 2 4 Reaction Coordinate 7. Is this reaction endothermic or exothermic? exotherm TC 8. Identify the…

Q: Carbon monoxide (CO) contains C-O bonds. Which if the following statements are true about the…

A: Given that, Carbon monoxide (CO) molecule contains C-O bonds.

Q: The partial pressure of oxygen in the lungs is about 150 mm of Hg. (The partial pressure is the…

A: Given, Partial pressure of oxygen in lungs = 150 mmHg Diffusion coefficient for oxygen = 2×10-11m2s

Q: Which of the following acid / base conjguate pairs is the best to make a buffer Solution? OA.…

A: A buffer is a solution that resists any change in pH on adding small amount of acid or base to it.…

Q: g2+(aq) + 2Cl(aq) at take place at the anode and at the cathode, the direction in which the…

A: In the electrochemical cell, Oxidation takes place at anode and reduction takes place at cathode.…

Q: Which of the following substances have meso forms? Draw them. (a) 2,3-Dibromobutane (b)…

A: 6.) Meso forms are drawn in Fischer projection . Meso form are those forms in which Compound have…

Q: An analytical chemist weighs out 0.410g of an unknown triprotic acid into a 250mL volumetric flask…

A: Given: Mass of triprotic acid (Assuming H3A) = 0.410 g. Concentration of NaOH = 0.0700 M And volume…

Q: Compound C 1) CrO3 / H30 H2O 2) H,0©/ HOCH, 3) NaOCH3 / HOCH3 4) H30®/ H20 5) NH,NH2 7 KOH Compound…

Concept explainers

Alkanes and Cycloalkanes

Alkanes are saturated organic compounds which are made up of C and H atoms. Alkanes have the general formula of CnH2n+2. Alkane contains sp3 hybridized carbon atoms with four sigmas (σ) bonds & every hydrogen atom is connected with one of the carbon atoms. The size of the alkane could be determined by the number of carbon atoms located in it.

Question

4. Reactivity. Propose a mechanism for each of the following transformations to
explain the observed regioselectivity and stereochemistry.
a.
-COCI
SiMe3
AICI3
Mé
`Me
76%
b.
Me
(Ph;P)4Pd (cat.)
CO-Me
EtzN, CH3CN, reflux
Me
MeO2C
80%
с.
Me
Me
SiMe3
n-BugNF
DMF, HMPA
69%
d.
EtAICI (2 eq)
toluene
-SiMe3
85%

Expert Solution

This question has been solved!

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

This is a popular solution!

SEE SOLUTION Check out a sample Q&A here

Step 1

Step 2

Step 3

Step 4

Trending now

This is a popular solution!

Step by step

Solved in 4 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

1. Predict the major products of the following reactions. Include stereochemistry where appeopriate. a. b. d. e. "Mo c. OH £. -OH -OH + HI + HBr X. Ota- + H₂C- OH OTS Jasfa F3C OH + HCI NaCN/DMSO OH OH Ja safa F3C OH SOCI₂ PBry ? CH₂S N DMSO
please show the detailed mechanism for each step for the reaction below. OTBDPS Me TMANO (anhydrous) (6 equiv) Co (CO) CH,Cl, -78 °C to r.t. 85% H. Me ОТВОPS triquinane
Determine the mechanism of nucleophilic substitution of each reaction and draw the products, including stereochemistr CH₂CH3 CI Br + CN d. + CH3COOH a. acetone + -OCH3 e. DMF f. b. C. ||||| a ||||| Br H Br CH2CH2CH3 + CH3OH DMSO H CH3 CI Br + OCH₂CH3 + CH3CH₂OH
1. Give the major product(s) of the following reactions as needed. Include any stereoisomers. NaOEt 1. Br NaOH Br 2. NaOtBu 3. A MEOH 4. Br 2. Which reaction will proceed faster A or B? H,S H2S "CI .... в
Complete the following reaction sequences by drawing the major products or the reagents necessary to make them. Be sure to include stereochemistry when appropriate. a. b. OEt TBSO "Вос 1. TsCl 23188- Et3N 2. CSA MsO OEt N TBSO Вос two steps 1. TBAF THF 2. LiOH THF 1. DIBALH 2 Ph₂p=/ CO₂Et * CO₂Et
stres (somer 19. Provide the reaction conditions necessary for the following transformations. Stereochemistry and Specific regiochemistry may be important. I getting regio isomers SN₂ reaction: retention (no change of OH ROH + ON a, Chival Ариа dikylation b. C. d. ✓ SN2 reaction need very String base امہ 1. 2. Lont OH type: type: CI 1. Nallt 2. vit DMF. 1. Soc1₂ 2. Sterificatia 1 2. CN but QUA Stercochemistry) ^ -14 сог bu OH + HOM
3. Draw the complete reaction mechanism in each step for the formation of compound C and D. i) ) PdCl (M CN), 1) -CH(CO,Et); Ph Ph. Ph (EtO,C)HC, N O li) co H- 60 - 95% R 97% de iv) Me,SnR co,Me ÓTMS Pd(OAc)2 CH,CN CO2Et 55%
Predict the reaction outcome showing and explaining proper Transition States. 6. Draw the major product with proper stereochemistry and explanation showing the correct approach of nucleophile. a) b) OMe NBn2 EtMgBr then H* Ph OLi H CHO Me then H* R Li d) SMe H ZnBH4 ? Ph. -N. ? then H+ R f) OSiMe₂Ph NaBH4 OH O NaHB(OAc) ? OSIMe2Ph is larger than Ethyl g) h) R = Et MeLi then H+ MeLi then H* R = OH and and ? R R = CO₂Me R = CO₂Me R R
1. .CI HC C: Li HC CH LICI 2. -CH3 OH Aqueous HO-S- -CH3 acetone g = SN1 Nucleophilic substitution Electrophilic a = Proton transfer addition h = SN2 Nucleophilic substitution b = Lewis acid/base e = El Elimination c = Radical chain f= E2 Elimination substitution Identify the mechanism by which each of the reactions above proceeds from the mechanisms listed. Use the letters a - i for your answers. among 1. 2.
1. Draw the intermediates A-C for reactions a and b. Please show the appropriate stereochemistry where necessary. RO hv .. RQ CO₂Me MO,C. Anti-tumour agent Coriolin co₂Me barrelene
What reagents are appropriate to carry out the conversion shown? - OH LOM 1. mCPBA; 2. CH3MgBr; 3. H₂O O 1. CH3MgBr; 2. H₂O O 1. mCPBA; 2. H₂O O mCPBA + enantiomer
c. Snl reactions dominate under polar protic solvents. Increasing the polarity of the solvent will increase the rate of the reaction because the polar solvent will stabilize the dispersed charges on the transition state more than it will stabilize the neutral reactant. Label areas of ô* and & on the molecules of the transition state of the SN1 reaction below: Me Me Ме Me Me H20 Br -Br OH + НО \'H Et Et RDS Et H Et Et transition state not isolable carbocation intermediate not isolable