Compound AA, C4H®O, gives a positive result (formation of a silver mirror) when reacted with Tollen's reagent. Reduction of compound AA with lithium aluminium hydride, LIAIH4 followed by acidified water, H3O* produces an alcohol, BB. Oxidation of BB with hot acidified potassium dichromate, K2Cr2O7 gives butanoic acid, C3H7COOH. Esterification between butanoic acid and methanol, CH3OH produces compound Cc. Dehydration of compound BB using concentrated sulphuric acid, H2SO4 at a temperature of 180°C produces compound DD.

Compound AA, C4H®O, gives a positive result (formation of a silver mirror) when reacted with Tollen's reagent. Reduction of compound AA with lithium aluminium hydride, LIAIH4 followed by acidified water, H3O* produces an alcohol, BB. Oxidation of BB with hot acidified potassium dichromate, K2Cr2O7 gives butanoic acid, C3H7COOH. Esterification between butanoic acid and methanol, CH3OH produces compound Cc. Dehydration of compound BB using concentrated sulphuric acid, H2SO4 at a temperature of 180°C produces compound DD.

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

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.47P: When warmed in dilute sulfuric acid, 1-phenyl-1,2-propanediol undergoes dehydration and...

See similar textbooks

Similar questions

Compound EE, C5H10O gives a positive result (formation of silver mirror) when reacted with Tollen’s reagent. Reduction of EE with sodiumborohydride, NaBH4 followed by acidified water, H3O+ produces compound FF. Dehydration of compound FF uses concentrated sulphuric acid, H2SO4 at a temperature of 180°C produces compound GG. Compound FF also reacts with hot acidified potassium dichromate, K2Cr2O7 to produce 2-methylbutanoic acid, C4H9COOH. Esterification between 2-methylbutanoic acid and methanol, CH3OH produces compound HH. Draw the structural formula of compounds EE, FF, GG, and HH.
When warmed in dilute sulfuric acid, 1-phenyl-1,2-propanediol undergoes dehydration and rearrangement to give 2-phenylpropanal. (a) Propose a mechanism for this example of a pinacol rearrangement (Section 10.7). (b) Account for the fact that 2-phenylpropanal is formed rather than its constitutional isomer, 1-phenyl-1-propanone.
Following is a retrosynthetic analysis for the synthesis of the herbicide (S)-Metolachlor from 2-ethyl-6-methylaniline, chloroacetic acid, acetone, and methanol. Show reagents and experimental conditions for the synthesis of Metolachlor from these four organic starting materials. Your synthesis will most likely give a racemic mixture. The chiral catalyst used by Novartis for reduction in Step 2 gives 80% enantiomeric excess of the S enantiomer.
a) Give the appropriate base for the above reaction and draw the resonance structures of the enolate ions derived from compound A. Then write the mechanism for the formation of the Dieckmann cyclized product B. b) If compound B above is reacted with NaBH 4 , draw the structure of the reduced product. Give a reason for your choice of product. c) Being a β-ketoester, B could undergo a 3-step synthesis involving alkylation, hydrolysis and decarboxylation reactions to yield the cyclopentanone, C. Write the outline synthesis for each step which include the appropriate regents and correct intermediate.
1. Compound A, C9H12, absorbs 3 equivalents of H2 on catalytic hydrogenation over palladium catalyst to give B, C9H18. On the treatment with acidic KMnO4, compound A gives among other things, a ketone that was identified as cyclohexanone. On reaction with NaNH2 in NH3, followed by addition of iodomethane, compound A gives a new hydrocarbon C, C10H14. What are the structures of A , B and C?
Compound 4 has two functional groups and it will formed an oily yellow liquid when it reacts with nitrous acid. They discovered that compound B is produced during the halogenation process of compound A. When compound B is reacted with nitric acid, compound C is formed. While Friedel Crafts alkylation of compound A produces compound D. Compound E was produced by Friedel Crafts acylation of compound A. This compound E reacts positively with alkaline iodine and 2,4-dinitropheny hydrazine. However, it returns negative results for Tollens* and Benedict's tests. a) Illustrate the potential 1H NMR spectrum for compound A. b) Identify the possible structural formula of compound A (according to the carbon type) based on your proposed 13C NMR spectrum. c) Predict the possible structural formula compounds B to E. The carbon atoms for compound A should be more than SIX (6). d) Distinguish between compound 4 with benzenedizonium chloride. e) Predict the possible chemical reaction for formation of…
. A colorless liquid, C4H6O, having a boiling point of 97-98°C was found to be soluble in water and also in ether. It gave a negative test for the presence of halogens, sulfur, and nitrogen. It did however, give a positive test to 2,4-dinitrophenylhydrazine reagent. It gave a negative result when treated with ceric nitrate solution and also Tollen’s reagent. Treatment with ozone followed by hydrolysis in the presence of zinc gave formaldehyde as one of the products. What is the structure and name of the colorless liquid?
Which of the following statements is correct? A) The haloform reaction proceeds under very difficult conditions and the yield is very low. B) The haloform reaction is used only for the identification of compounds containing secondary alcohol groups. C) Methyl ketones or alcohols are oxidized with halogens in acidic solutions to give carboxylic acids and the appropriate haloform product. D) Enolate anions react rapidly with halogens to give alpha-halocarbonyl compounds.
Butanone undergoes a nucleophilic addition with a Grignard reagent made from 1-bromopropane and magnesium metal in THF solution. The alkoxide formed from the nucleophilic addition is then conveted into the final product by the careful addition of dilute acid. Complete the mechanism by following the instructions provided for each step. Step 1. Nucleophilic Addition in THF
Benzene, C6H6 undergoes substitution reaction with concentrated nitricacid, HNO3 to produce compound L. The reaction of compound L withbromine, Br2 in the presence of iron tribromide, FeBr3 produced compoundM. Benzene also undergoes Fridel-crafts alkylation reaction withchloroethane, CH3CH2Cl using catalyst N to produce compound P (i) Draw the structural formula of L, M and P (ii) State catalyst N. (iii) Show the formation of electrophile that will be reacted with benzene for theformation of compound P.
What reaction would be best for preparing 2-isopropoxy pentane in high yield? 2-iodopentane and sodium isopropoxide sodium hydride added to 2-pentanol, then 2-iodopropane mercury acetate added to 1-pentene and isopropanol, then NaBH4 mercury acetate added to 2-pentene and isopropanol, then NaBH4
An unknown alkyl chloride, designated as compound F, forms a Grignard reagent which on treatment with water yields a compound whose formula is C7H16. When compound F is treated with sodium metal 2,2,9,9-tetramethyldecane is formed. What is the structure of compound F? Show your line of reasoning including all equations.