Isoerythrogenic 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.

Based on the data given above, the line structure is shown below- It is also known as isanic acid.

Isoerythrogenic 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, CH20, malonic acid, HO2CCH2CO2H, adipic acid, HO2C(CH2)4CO2H, and the aldehyde carboxylic acid, OHC(CH2)6CO2H. Provide a structure for isoerythrogenic acid.

Isoerythrogenic 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, CH20, malonic acid, HO2CCH2CO2H, adipic acid, HO2C(CH2)4CO2H, and the aldehyde carboxylic acid, OHC(CH2)6CO2H. Provide a structure for isoerythrogenic acid.

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

See similar textbooks

Related questions

Q: The following substances can be prepared by a nucleophilic addition reaction between an aldehyde or…

A: The given compound is a ketal. Ketals are formed when a ketone reacts with two equivalents of an…

Q: The reaction of N−bromosuccinimide with 4−methyl−3−nitroanisole has been reported in the chemical…

A: N- bromosuccinimide gives free radical substitution at allylic position.

Q: Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing…

A: The attack of a ylide on a carbonyl compound is known as the Wittig reaction. In this reaction, the…

Q: Butanol is treated with H2SO4 and heat. Identify the reaction and give the product that can be…

A: When alcohols are treated with H2SO4 and provided heat, then elimination reaction takes place and…

Q: Draw the structure of sodium tetradecyl sulfate and ciprofloxacin and state how the activity of the…

A: The key components associated with a molecule that is responsible for providing the characteristic…

Q: (a) Explain how NaBH4 in CH3OH can reduce hemiacetal A to butane-1,4-diol (HOCH2CH2CH2CH2OH). (b)…

A: (a) The given compound A is a hemiacetal. Sodium borohydride (NaBH4) is a strong reducing agent. It…

Q: Trimyristin is obtained from coconut oil and has the molecular formula C45H86O6. On being heated…

A: Given : Trimyristin. To find : Desired product from the reaction. Solution : As we know that,…

Q: Synthesize the o-form of amino benzoic acid from benzene.

A: Synthesis of o-form of amino benzoic acid from benzene is given below

Q: Draw the structure of the products expected when cyclobutylmethanol is heated with concentrated…

A: •Here reaction is given in between:- Cyclobutylmethanol + Conc.H2SO4 ===> Product

Q: Compound A of molecular formula C8H14 is reduced by sodium in liquid ammonia to give compound B of…

Q: The synthesis of tetraphenyl porphorin begins with an electrophilic substitution reaction. Write an…

A: The reaction scheme is generally framed by considering the factors like atom availability and…

Q: 2,2-dimethyl-1-propanol

A: Since you have posted a question with multiple sub-parts, we will solve the first three subparts for…

Q: H₂C H₂C ممل CH3 CH3 Aldehydes and ketones react reversibly with two equivalents of alcohol in the…

A: The objective of the question is to predict the suitable mechanism for the given reaction.Ketal…

Q: One step in the gluconeogenesis pathway for the biosynthesis of glucose is the partial reduction of…

Q: Under milder temperatures than what is needed for dehydration, strong acids catalyze the…

A: `The formation of di-n-propyl ether from 1-propyl alcohol under strong acidic conditions is a…

Q: 4. Hydrocarbon A has the molecular formula C14H10C12. It absorbs eight molar equivalents of any…

A: C14H10Cl2 = DBE = 14 - 10+2/2 + 1 = 15 - 6 = 9 = *8+1 = 8 double bonds or 4 triple bonds + 1 ring.…

Q: Predict the structural formula of the major product of the reaction of 2,2,3-trimethyloxirane with…

A: The reaction between 2,2,3-trimethyloxirane and ) Me2NH gives hydroxyl amines Dimethylamine will…

Q: The ethylation of benzene is an electrophilic substitution reaction. Identify the electrophile in…

Q: Consider the compound C5H9B (Compound X). It reacts with potassium tert-butoxide to give Compound Y,…

Q: Benzene can be hydroxylated by treating it with hydrogen peroxide and a strong acid such as…

A: Given reaction:

Question

Isoerythrogenic 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.

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

VIEW

Step 2

VIEW

Trending now

This is a popular solution!

Step by step

Solved in 2 steps with 1 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

Ph3P-CHCH3 H₂C H3C Aldehydes and ketones are converted into alkenes by means of a direct nucleophilic addition called the Wittig reaction. In the reaction, a triphenylphosphorine ylide, also called a phosphorane, adds to an aldehyde/ketone to give a four-membered cyclic intermediate called an oxaphosphetane. The oxaphosphetane is not isolated but instead spontaneously decomposes to release triphenylphosphine oxide and an alkene. CH3 00 + The ylide is formed by reaction of triphenylphosphine, a good nucleophile, with a primary alkyl halide in an SN2 reaction, followed by deprotonation of the carbon with a strong base, such as butyllithium. The carbonyl carbon and the carbon originally bonded to the halogen become the two carbons with the double bond in the product alkene X m CH3 The real value of the Wittig reaction lies in its ability to yield an alkene of predictable structure, as the C=C bond is precisely where the C=O bond was in the reactant and no isomers (other than E/Z isomers)…
the organic compound 2-heptanone, belonging to the ketone family, is responsible for the strong penetrating odor in Roquefort cheeses. Starting from acetylene as the starting reagent, propose a synthesis line with the reaction mechanisms involved for the synthetic obtaining of 2-heptanone and use it as a food additive in analogous cheeses.
Reaction of p-nitroaniline with sodium nitrite and hydrochloric acid at 0 °C, followed by treatment with N,N-diethylaniline.
Sharpless epoxidation of allylic alcohol X forms compound Y. Treatment of Y with NaOH and C6H5SH in an alcohol–water mixture forms Z. Identify the structure of Y and draw a mechanism for the conversion of Y to Z. Account for the stereochemistry of the stereogenic centers in Z. Z has been used as an intermediate in the synthesis of chiral carbohydrates.
Prostaglandins are a class of cicosanoids, fatty acid derivatives with a variety of extremely potent actions on vertebrate tissues. They are responsible for producing fever and inflammation and its associated pain. Prostaglandins are derived from the 20- carbon fatty acid arachidonic acid in a reaction catalyzed by the enzyme prostaglandin endoperoxide synthase. This enzyme, a cyclooxygenase, uses oxygen to convert arachidonic acid to PGG2, the immediate precursor of many different prostaglandins. Rate of formation of PGG2 with 10 mg/ml ibuprofen (mM/min) Arachidonic acid (mM) Rate of formation of PGG2 (mM/min) 0.190 12.3 0.228 13.9 0.342 17.5 0.570 1.33 22.2 28.8 7.71 8.88 11.9 16.3 24.0 The kinetic data given in the table are for the reaction catalyzed by a mutant of prostaglandin endoperoxide synthase. Focusing here on the first two columns, determine the Vmax and Km of the enzyme. Vmax = Km mM/min mM
A dialkyl-substituted benzene, C14H22, is treated with basic potassium permanganate, followed by acid workup. The same dialkyl-substituted benzene was recovered afterward from the reaction mixture. Draw the structure of the compound.
Compound A, CH10, was found to be an optically active alcohol. Despite its apparent unsaturation, no hydrogen was absorbed on catalytic reduction over a Pd/C catalyst. On treatment of A with dilute H,SO, dehydration occurred and an optically inactive alkene B, CH4 was produced as the major product. Alkene B, on ozonolysis, gave two products. Product C, C,H,0, was shown to be an aldehyde while product D, CHg0, was shown to be a ketone. Draw the structure of compound C. • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. In cases where there is more than one answer, jtust draw one.