Current Attempt in ProgressPropose a plausible mechanism for the following transformation:HO19.55H[H3O+]EtOHCorrect. Formation of a hemiacetal follows a common pattern for mechanisms of acid-catalyzed reactions: Protonate,Attack, Deprotonate (P.A.D.).The first three steps of the mechanism involve the formation ofThe first step is protonation of the carbonyl oxygen atom VThe second step is nucleophilic attackThe third step isdeprotonation of a positively charged oxygen atoma hemiacetal Part 5Incorrect. Which of the four mechanistic steps is happening?Add two curved arrow(s) to draw step 5 of the mechanism: collapse of a charged tetrahedral intermediate. Modify the givendrawing of the product as needed to show the intermediate that is formed in this step. Use the +/- tools to add/remove charges,and use the single bond tool to interconvert between double and single bonds.HintHHEdit DrawingThe next step is loss of a leaving group.LOHAssistance Used

Given is a reaction of conversion of 5-hydroxypentanal to 2-ethoxytetrahydro-2H-pyran.

Answered: Propose a plausible mechanism for the…

Science

Chemistry

Propose a plausible mechanism for the following transformation: HO H [H3O*] EtoH

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter23: Carbonyl Condensation Reactions

Section23.SE: Something Extra

Problem 45MP

See similar textbooks

Related questions

Q: In determining the volume of CO2 in the flask, the flask was filled with water and the total volume…

A: The objective of the question is to understand the impact of the presence of air bubbles under the…

Q: to an 5. How many moles would be contained in each of the following: a. 1.2 g of silver b. 5 lb of…

A: Given,a. 1.2 g of silverb. 5 lb of sugar ( C12H22O11 ) c. 4 tons of bauxite ore ( Al2 )

Q: Cl2 HO

A: Electrophilic addition reactions are a class of chemical reactions in which an electrophile (an…

Q: 5. Propose a synthesis for the following product from the starting material(s) indicated. Show all…

Q: 21. Consider the reaction Hg (aq) + Hg(1) Hg(aq). Find the equilibrium constant for this reaction at…

A: The standard half reactions are 2Hg2+ (aq) + 2e− ---------> Hg22+ (aq) E° = 0.92 V…

Q: Write down the common (not IUPAC) names of the organic molecules that would be released if this…

A: The objective of the question is to write the common names of the organic molecules that are…

Q: Katie McGeough Jamison lab NH₂ nodod OH до новодо TDF Concept question: Which mechanism(s) can the…

A: The mechanism can be followed by the given halide given below.

Q: 3. Complete the statements below to give the specific selection rules for microwave absorption…

Q: RCO3H

Q: (1) :0: .. 2НСI products? + mechanism

A: Lone pair of Oxygen attacks to H+ forming a protonated ether then Cl- attacks to carbon adjacent to…

Q: Propose an efficient synthesis for the following transformation: (a) The transformation above can be…

A: The question is based on the concept of organic synthesis.We need to synthesize the product using…

Q: At what temperature, in degrees Celcius, is the solubility of ammonium chloride 50 g per 100 g of…

A: Maximum amount of solute which can be dissolved in a solvent at a particular temperature is called…

Q: Which of the following Lewis structures best represents the bonding in BaO? O [Ba:][0] O…

A: Lewis’s bonding theory is based on the octet rule. The Lewis structure is a simplified…

Q: 1) Write both the common name and the IUPAC name for the following compound. N

A: To write, the IUPAC name of a given compound, first identity the functional group present in it.…

Q: R-carvone is responsible for the characteristic minty odor and flavor of spearmint oil, and its…

A: Sigma bond between C2-C3 occur due to overlapping of Sp2-Sp2 orbitals. This bonding occur in yz…

Q: c. Explain how 10% sodium bicarbonate can be used to separate a mixture containing benzoic acid and…

A: Separating a mixture of organic compounds often involves exploiting differences in their chemical…

Q: How many grams of solute are in 2000. mL of a 5.00 ppm solution?

A: Definition of ppm concentration term is ppm =

Q: The following information is given for magnesium at 1atm: boiling point 1090 °C melting point 649 °C…

A: The mass of liquid magnesium sample = Normal melting point of liquid magnesium = We have to…

Q: Find the concentration of hydroxide, OH-, ions in a 0.100 M solution of HOAc, acetic acid

Q: Draw the structural formula of the product of the reaction shown below. + H₂O H₂SO4 . You do not…

Q: Draw the major product of this reaction. Ignore inorganic byproducts. HBr (excess) Drawing Problem…

A: The addition of two or more equivalents of HBr converts alkynes to geminal dihalides through an…

Q: Determine the volume of 0.220 M KOH solution required to neutralize each sample of sulfuric acid.…

Q: The following information is given for benzene, C6H6, at 1 atm: boiling point = 80.1 °C specific…

A: The number of moles of benzene(n) =

Q: Predict the products of the following biochemical reaction: CH₂ C-(CH₂)6 - CH3 || CH—O–C−(CH2)6 —…

A: Saponification is a process involving the hydrolysis of fats on its reaction with alkali, thereby…

Q: What would be the pH of a solution that produces H3O+ ions at a concentration of 3.7 x 10-4 M? Write…

A: Concentration of hydronium ion , [H3O+] = 3.7×10-4 M To determine: pH of solution

Q: 3. Compounds with a carbon - carbon double bond (such as ethene) add hydrogen in a reaction called…

A: (1) (2) (3) (4)

Q: 3. Provide the missing reaction products and propose a detailed catalytic cycle (reaction…

Q: 5. "S". Draw the skeletal structures of the products obtained and label all chiral carbon atoms as…

A: An arrow always depicts from a region of high electron density to low electron density ; that is…

Q: Provide an IUPAC name for each of the compounds shown. (Specify (E)/(Z) stereochemistry, if…

A: In the first step, identify the functional group present.Identify the longest carbon chain…

Q: What concentration of SO is in equilibrium with Ag₂ SO₂ (s) and 5.30 x 10-³ M Ag*? The Ksp of Ag,…

A: Given:[Ag+] = 5.30 x 10-3 MKSp of Ag2SO3 = 1.50 x 10-14So we have to determine concentration of…

Q: Tu Please don't provide the handwriting solution

A: Hydration of alkenes is the acid catalyzed reaction to form the alcohol. This reaction involves the…

Q: 4. Calculate the Boltzman distribution for this instrument at 20°C. What increase in sensitivity…

A: The Boltzmann distribution describes the statistical distribution of particles in a system at a…

Q: please show all steps involved with this question, thank you! 5. For the following molecule, how…

A: An arrow always depicts from a region of high electron density to low electron density ; that is…

Q: 3.) A solution containing the triborate anion, B.O.(OH)4 (a), is titrated with 0.200 M HCI (you may…

Q: Draw out the 1,2-insertion product that forms in this reaction. Rh H H Xa- 1 1,2-insertion product

A: 1,2 insertion also known as migratory insertion creates a vacant site in metal. In this reaction H…

Q: Aniline (C6H5NH2), an organic amine and a weak base with Kb of 4.0×10-10 reacts with water to form…

A: The dissociation constant of the base = The equation for dissciation = ?The expression for…

Q: Calculate the change in heat when 18.50 g of water vapor (steam) at 100.0°C condenses to liquid…

A: The heat for the above process will be given by 1) amount of heat change on condensing water vapour=…

Q: 9. a. Show the product(s) that would result from the indicated mechanisms: Vi CI H -: NH3 xyl H Br:…

A: reaction mechanism is the sequence of elementary steps by which a chemical reaction occurs. Arrow…

Q: 5. Identify A-I F H₂O NBS heat H E MeO' B с HBr ROOR (i) 0, (ii) DMS NaBH₁ H₂O D

A: This is an organic synthesis question. It requires knowledge of formation of alkenes and their…

Q: Br O HO HO A NH Br H Br H₂, Pt Br HO HO NH₂ NH₂ + A NH₂ HNO3 Br. B

A: When an alkyl nitrile reacts with H2/Pt, it will be reduced to a primary amine.

Q: The spacings of the rotational fine structure lines of carbon dioxide 12C160₂ are determined from IR…

Q: 1. Propose two different plausible syntheses for the following transformation using reactions you…

A: Given is organic synthesis reaction. The given product has 2 carbon extra than the reactant.We can…

Q: CH3 Use the Williamson Ether Synthesis to prepare (Any necessary reagents and solvents can be used).…

A: Information of question

Q: There are two compounds which have the chemical formula C4H10. L L What intermolecular forces are…

A: A question based on intermolecular forces of attraction. For the 4 sub-division questions, answers…

Q: Draw the structural formula(s) for the organic product(s) formed when the following compound is…

Q: Which of the compounds below is an example of a network solid? A) C25H25(S) B) NaCl(s) C) SiO₂ (s)…

A: The classification of solids is a fundamental aspect of understanding the diverse nature of…

Q: 3) Which of the following compounds is most soluble in water? NH₂ `N´ || `N

A: As we know water is a polar solvent. Polar substances tend to dissolve in polar solvent and…

Q: 16) An average dairy cow produces 10,896 grams of methane gas, CH., each year. What volume of CH. is…

A: Answer:Dalton's law of partial pressure states that partial pressure of any gas in the gaseous…

Q: 1. Name this amine properly. Is it a primary, secondary, or tertiary amine? 2. Which of the…

A: Information of question

Q: For the following quetion please read carefully the question and instruction. PLEASE ANSWER QUESTION…

Concept explainers

Aromatic Compounds

Aromatic organic compound or aromatic system is an important class of hydrocarbons under the branch of organic chemistry. Aromatic compounds are also called arenas. The definition of aromatic organic compounds can be stated as a class of organic compounds with a planar cyclic ring of atoms bonded through alternated single and double bonds. Due to these alternating bonds, a peculiar feature termed as ‘resonance’, that is, delocalization of pi electrons or the electrons is shared within the atoms of the ring which are present in the aromatic compounds. The word ‘aromatic’ includes a Greek word ‘aroma’ which means smell, indicating that they were named as such due to the sweet odor they produce. Many well-known flavors such as vanilla, cinnamon, and few scents from flowers are extracted from aromatic compounds. Benzene with chemical formula C6H6 is a very common aromatic compound that contains six atoms of carbon held in the cyclic ring of alternate double bonds. It is also to be noted that not all aromatic compounds contain benzene ring. This can be explained by Huckel’s rule.

Question

Current Attempt in Progress
Propose a plausible mechanism for the following transformation:
HO
19.55
H
[H3O+]
EtOH
Correct. Formation of a hemiacetal follows a common pattern for mechanisms of acid-catalyzed reactions: Protonate,
Attack, Deprotonate (P.A.D.).
The first three steps of the mechanism involve the formation of
The first step is protonation of the carbonyl oxygen atom V
The second step is nucleophilic attack
The third step is
deprotonation of a positively charged oxygen atom
a hemiacetal

Part 5
Incorrect. Which of the four mechanistic steps is happening?
Add two curved arrow(s) to draw step 5 of the mechanism: collapse of a charged tetrahedral intermediate. Modify the given
drawing of the product as needed to show the intermediate that is formed in this step. Use the +/- tools to add/remove charges,
and use the single bond tool to interconvert between double and single bonds.
Hint
H
H
Edit Drawing
The next step is loss of a leaving group.
LOH
Assistance Used

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: Introduction

VIEW

Step 2: The mechanism of the reaction

VIEW

Step 3: Mechanism leading to the product

VIEW

Solution

VIEW

Step by step

Solved in 4 steps with 7 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

CH3 NH3, H* H3C H3C CH: Substituted pyrroles are often prepared by treatment of a 1,4-diketone with ammonia in the presence of catalytic H*. The mechanism involves the following steps: 1) Protonation of the carbonyl oxygen and nucleophilic attack by ammonia form tetrahedral intermediate 1; 2) Proton transfer leads to protonated carbinolamine 2; 3) B-elimination leads to enamine 3; 4) Protonation of the carbonyl oxygen and nucleophilic attack by the amine form tetrahedral intermediate 4; 5) Proton transfer leads to protonated carbinolamine 5; 6) B-elimination leads to the final product. Write out the reaction mechanism on a separate sheet of paper, and then draw the structure of tetrahedral intermediate 4. • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. Do not include lone pairs in your answer. ZI
Jut L Br HNO3/H₂SO4 NaOEt M N K (i) Give the structure of M and a mechanism for its formation. L and of bromoquinoline Explain the reactivity regioselectivity of the reaction. (ii) Give the structure of N and a mechanism for its formation. and bromoquinoline L Explain the reactivity of regioselectivity of the reaction.
3. Provide a mechanism for the following transformation: Ph CI (2 eq.) 2 eq. NaCN 4. Provide a mechanism for the following transformation: S H₂O NC CN Ph Ph OH of OH
give the product of the following reaction A MeO Structure A Structure B Structure C Structure D OH B MeOH/MeO- +H (cat.) MeO OH C HO ??? OMe D HO OME
Reaction of phenol with acetone in the presence of an acid catalyst gives a compound known as bisphenol A, which is used in the production of epoxy and polycarbonate resins Propose a mechanism for the formation of bisphenol A. OH H;PO, + H,O НО HO Phenol Acetone Bisphenol A
Rank the following carboxylic acid derivatives in decreasing order (most to least) of reactivity towards nucleophilic substitution CI NH2 OCH3 ONa II IV OI> IV> III > || O > IV > || >I O I> II| > || > IV O II > IV > 1> I
Propose a plausible mechanism for the following transformation: 1) Excess MeMgBr 2) H₂O HO
4. Propose a mechanism for the following reaction: Conc. H₂SO4 HO
3. Propose a plausible mechanism for the following transformation: & Q & CF3 H₂N CN 'N CF HOH
Alkyl diazonium salts are unstable even at low temperature. They decompose to form carbocations, which go on to form products of substitution, elimination, and (sometimes) rearrangement. Keeping this in mind, draw a stepwise mechanism that forms all of the following products. NANO2 он + HCI, H2O NH2 он
The structure shown below is of Pitolisant (Waxix®), is a drug to treat narcolepsy. CI Pitolisant – Waxix® Below, see the synthesis of the compound. What are the reactions used? OMs OH OH CI CI O Two Williamson ether synthesis reactions. O Aminal formation followed by an ether interchange reaction. O An SN2 reaction followed by a Williamson synthesis.
Identify compounds A and B from the following reaction sequence LINH lig MeO 0 (Ozone) MeOH Me₂S B