3. When compound 11 is treated with two equivalents of methansulfonic acid (MSOH) in dichloromethane, the pyrazole 12 and hydrazine 13 are obtained (after the reaction mixture has been neutralized): OMe COME OMe MSOH CH,Cl, EtO EtO 11 12 13 OEt Propose a reasonable mechanism!

3. When compound 11 is treated with two equivalents of methansulfonic acid (MSOH) in dichloromethane, the pyrazole 12 and hydrazine 13 are obtained (after the reaction mixture has been neutralized): OMe COME OMe MSOH CH,Cl, EtO EtO 11 12 13 OEt Propose a reasonable mechanism!

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: 11 8. When benzene is treated with Reagent(s) A followed by Reagent(s) B, Compound P (CaHCIO) is the…

Q: l Aldehydes and ketones react reversibly with two equivalents of alcohol in the presence of an acid…

A: Ketal formation is a chemical reaction in which a ketone reacts with two equivalents of alcohol (or…

Q: 11. A chemist performed the following reactions converting an alcohol into an alkyl bromide using…

Q: Which of the following correctly depicts the first step of the mechanism for the reaction shown?…

A: Given is hydrazone synthesis reaction.Ketone reacts with hydrazine to form hydrazone.

Q: Cyclohexene can be converted to 1-cyclopentenecarbaldehyde by the following series of reactions. СНО…

A: Oxidation using OsO4/H2O: Reactant in presence of OsO4/H2O undergoes oxidation produce vicinal…

Q: How many alkenes are formed by eliminating HCI from 3-chloro-3,4- dimethylheptane in methanol,…

A: E1 elimination:This is an unimolecular elimination reaction, it proceeds through the carbocation…

Q: Treatment of (CH3)2CHCH(OH)CH2CH3 with TsOH affords two products(M and N) with molecular formula…

A: Given: When (CH3)2CHCH(OH)CH2CH3 is treated with TsOH, the products M and N having molecular formula…

Q: The following reaction failed to deliver the desired product, instead giving a molecule with a…

Q: H3C N- H₂NNH₂ H⭑ CH3 H3C IN CH3 Hydrazine reacts with 2,4-pentanedione to yield…

A: Step 1: Step 2: Step 3: Step 4:

Q: Br CH,CO,H +Br, CH,CO,H CH3 `CH,CO,H CH3 A bromolactone

Q: 3) Propose products (if any) and mechanisms for the following AICI3-catalyzed reactions:…

Q: OH OAc HOʻ excess Ac,0 AcO HO -OH pyridine, 0°C AcO- OAc OH OAc Compound 4 Compound 3 HBr OCH3 OAc…

A: Here we are required to show the derailed me mechanism for conversion of compound 5 to compound 6

Q: 5-Androstene-3,17-dione is isomerized to 4-androstene-3,17-dione by hydroxide ion. Propose a…

Q: 1. OH HBr 2. H3C-O + H3C-O-Li LOH2 Br a = Proton transfer b = Lewis acid/base d = E1 Elimination e =…

A: 1. In the first reaction the oxygen group of the cyclohexanol acts as a base and abstract the proton…

Q: 10. Treatment of 1,2-dibromoethane with the dithiolate dianion shown in the reaction below leads to…

A: Sulphur ion is a good Nucleophile and thus attacks the carbon attached with Bromine atom as below.

Q: 8. Which compound reacts most rapidly with cyanide ion in a polar, aprotic solvent? (A)…

A: Solution- SN2 is single machanism where the attack of nucleophile and leving of the group accurs…

Q: Treatment of (CH3)2CHCH(OH)CH2CH3 with TsOH affords two products (M and N) with molecular formula…

Q: 14. When propylene reacts with hydrogen bromide in the presence of a peroxide initiator, which of…

Q: Treatment of a hydrocarbon A (molecular formula C9H18) with Br2 in the presence of light forms alkyl…

A: Since Ozonolysis of D forms cyclohexanone and acetone. and we knwo that in ozonolyisis reaction, the…

Q: Identify compounds A and B from the following reaction sequence Li/NH3 liq. MeO (Ozone) MeOH Me₂S B

A: Given that, a reaction scheme is shown below We have to complete the above reaction sequence.…

Q: Br Br2 CH3 CH3 H3C° CH2Cl2 H3C Br Electrophilic addition of bromine, Br2, to alkenes yields a…

A: Alkene are reactive in nature due to unsaturation

Q: لله - od This B-diketone can be synthesized from cyclohexene and cyclopentanone using an enamine…

Q: 21. Consider the reaction scheme below Br H3O* Mg коН (aq) Y CH3CH2CCH2CH3 X Ether Reflux ČH3…

Q: 7. An unknown amine X has the molecular formula C8H₁7N. Treatment of amine X with excess CH31…

A: Here an unknown amine X( C8H17N) when undergo Hoffman exhaustive methylation followed by…

Q: 2,4-D is a synthetic auxin (a plant hormone) used in the control of broadleaf weeds, and one of the…

Q: Propose a mechanism to account for the following reaction of an enamine with an alkyl halide: N-…

A: The reactivity of enamines as nucleophiles is due to the dipolar character of the one of the…

Q: Write a mechanism that accounts for the formation of ethyl isopropyl ether as one of the products in…

A: Given that, a reaction scheme is We have to draw the mechanism for the formation of the ethyl…

Q: In the reaction of NaBH4 with formaldehyde in methanol sovlent, the products are BH3, CH3OH and…

A: NaBH4 is a strong reducing agent.

Q: The reaction of (2S)-2-chloro-3-methylpentane with sodium iodide yields two products:…

A: In SN-2 mechanism, usually inversion of configuration occurs because nucleophile attacks from…

Q: SA. Identify the product and write a detailed mechanism to account for its formation CH3 H,o PRODUCT…

A: Since you have posted multiple questions, we are entitled to answer the first only.

Q: 2. Indicate reagents or conditions for the following transformations involving rearrangements.…

A: As per the rules only first three question can be answered.

Q: The base-promoted rearrangement of an a-haloketone to a carboxylic acid, known as the Favorskii…

A: Given is organic reaction. The given reaction is Favorskii rearrangement. It is a base-promoted…

Q: Propose products (if any) and mechanisms for the following AlCl3-catalyzed reactions:…

A: The details solution for this is provided below in step II.

Q: Provide the product for the following transformation: A A B B C C D D E E 1. NaOMe, MeOH, heat 2.…

A: The given reaction is a multistep reaction in which various reaction mechanisms are involved. Let's…

Q: 3H. Put it all together. Predict the E1 products of the following reaction. Label alkenes as E/Z. OH…

A: The objective of this question is to predict the E1 product for the given reaction.In the…

Q: Can you draw out the following reaction mechanism: 1. Benzyl alcohol + H2SO4 → Benzyl oxonium ion +…

A: The oxidation of benzyl alcohol can be achieved by the treatment of Jones reagent (CrO3, H2SO4) to…

Q: resonance forms to show how the cyano group activates the double addition

A: Mechanism

Q: Propose a plausible mechanism for the following transformation: [H3O+] HO H EtOH 19.55 The first…

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

Q: Alkylation of benzene with 1-chlorobutane in the presence of AlCl3 gave not only the expected…

Q: 5. Solvolysis of bromomethylcyclopentane in methanol gives a complex product mixture of the…

Q: 9. (a) Under certain conditions, the reaction of 0.5 M 1-bromobutane with 1.0 M sodium methoxide…

A: (a) Given data : Rate = 0.05 mol L-1 sec-1 At this rate, Concentration of 1-bromobutane = 0.5 M…

Q: What reagents are needed to synthesize the following bromides? Br Br Provide the major organic…

A: The reactions involving organic compounds are called organic reactions. Organic reactions are of…

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

3. When compound 11 is treated with two equivalents of methansulfonic acid (MSOH) in
dichloromethane, the pyrazole 12 and hydrazine 13 are obtained (after the reaction mixture
has been neutralized):
COMe
OMe
OMe
MSOH
2
EtO
CH,Cl,
EtO
H.
11
12
13
OEt
Propose a reasonable mechanism!

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 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

The following reactions involve combinations of pericyclic reactions. Give detailed mechanisms for each transformation. Be sure to illustrate all observed stereochemistry. Identify (by name) the pericyclic reaction(s) in each example. v. vi. + ACO V. NC NC vi. MeO OMe 110 °C OMe CN BC CN OMe m AcO
Friedel–Crafts alkylations can be carried out with carbocations formed from reactions other than the reaction of an alkyl halide with AlCl3. Propose a mechanism for the following reaction:
2-phenylethanol, a molecule extensively used in perfumery, can be prepared by treating benzene with ethylene oxide in the presence of a strong acid catalyst. Propose a mechanism for this reaction, showing all resonance forms of the sigma complex intermediate. [H+] OH
X6-156. Arrange the following substituted anilines in increasing order of reactivity toward acetic anhydride: sllo NH2 ร้อเป็น NH2 NH2 edi NH2 O₂N. (a) (b) ---- (c) (d) bund NO2 CI H3C-N-CH3 Insmiy X 6-157. Suggest a mechanism for the preparation of acetic anhydride from acetic acid and acetyl chloride in the presence pyridine (an amine base).
When pent-1-ene is treated with mercury(II) acetate in methanol and the resulting product is reacted with NaBH4, what is the primary organic compound which results? 1-ethoxypentane 1-methoxypentane 3-ethoxypentane 2-ethoxypentane 2-methoxypentane
lo CI H3C H3C 07 ↔X + :0: OH Dimethylaminopyridine (DMAP) is often used as a catalyst in esterification reactions. A basic solvent such as triethylamine is used to react with the liberated proton from the alcohol group. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CI NMe₂ N(CH₂CH3)3 CH3 6--10-- NMe2
10. Propose a mechanism for the benzoin condensation, which is specifically catalyzed by cya- nide: () 2Ar-C-H CH₂-C-CH₂-C-H CN O OH Ar-C-C-Ar H 11. Propose a mechanism for the following transformation: COOC H. Nall COOC₂H₂ H₂C-CH-PPh,Br H₂C coỌC H COOCH, + Phụ P=0
In an SN2 reaction between 2-chlorobutane and iodide ion, what happens to the rate of the reaction if: (a) the concentration of 2-chlorobutane is doubled? (b) the concentration of iodide is doubled?
10-Bromo-a-chamigrene, a compound isolated from marine algae, is thought to be biosynthesized from y-bisabolene by the following route: "Br* Bromonium Cyclic carbocation -H*) Base ion Bromo peroxidase Br y-Bisabolene 10-Bromo-a- chamigrene
H₂C ཏཱཏི 1 ནི OH 1. Br2, PBг3 2. H₂O H3C OH Br The a-bromination of carbonyl compounds by Br2 in acetic acid is limited to aldehydes and ketones because acids, esters, and amides don't enolize to a sufficient extent. Carboxylic acids, however, can be a-brominated by first converting the carboxylic acid to an acid bromide by treatment with PBr3. Following enolization of the acid bromide, Br2 reacts in an a-substitution reaction. Hydrolysis of the acid bromide completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions :0: H3C Br Br + :::OH2 Br H₂O H3C Br за
1. Propose reasonable mechanisms for the following transformations: OH H+ 女 Η
5-The hydrolysis of a series of ethyl benzoates by hydroxide ion in 85% aqueous ethanol has been investigated. A Hammett plot of the second order rate constants (Ku) gave a reaction constant p = 2.56. Calculate how much faster ethyl 4- nitrobenzoate will undergo base catalyzed hydrolysis compared to ethyl benzoate under similar conditions. ON 6-The PKa of p-chlorobenzoic acid is 3.98, and that of benzoic acid 4.19. Calculate o-value of p-chloro group.