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.

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.

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

Chapter11: Ethers, Epoxides, And Sulfides

Section: Chapter Questions

Problem 11.41P: Aldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in...

See similar textbooks

Similar questions

Structure of product C A hydrocarbon, A, with formula C11H16 undergoes hydrogenation with Pd to give product B, C11H22, and with Lindlar's catalyst to give product C, C11 H18. Ozonolysis leads to a mixture of products including cyclohexanone and 4-oxobutanoic acid. Treatment with sodium amide (NaNH2) followed by bromoethane gives compound D, C13H20. Draw possible structures for A, B, C, and D. H₂, Lindlar's Problem 13 of 14 Structure of A 1. NaNH2 Submit 2. CH3CH₂Br Structure of product D
Grignard reagent is a versatile tool in synthetic organic chemistry. Using bromocyclopentane as a starting material, show how a Grignard reagent, X, is synthesized. Reaction of X with water produces compound Y while treatment in carbon dioxide followed by hydrolysis forms compound Z. 3-methyl-2butanone reacts with X and hydrolyses to yield compound AA. Draw the structural formulae of compounds Y, Z and AA and write the chemical equations respectively.
Compound AA has a molecular formula of C3H6O and gives a positiveresult using Tollen’s reagent. The reaction of compound AA with hotacidified potassium permanganate, KMnO4 gives compound BB. Thecatalytic hydrogenation of compound AA with nickel, Ni producedcompound CC. The reaction of compound BB with ethanamine,CH3CH2NH2 produces compound DD I) Draw the structural formula of compounds AA, BB, CC and DD. 2)Name the type of chemical reaction for the formation of compound CC.
Consider the compound C5H9Br (Compound X). It reacts with potassium tert-butoxide to give Compound Y, C5H8. Compound Y upon reaction with hydrogen produced methylcyclobutane. Compound Y upon reaction with ozone produces one compound with two aldehyde functional groups. Provide the structures of Compound X and Y.
Compound T (C6H6O) reacts with sodium hydroxide to form Compound U. Compound V can be formed when Compound T reacted with sodium. Compound W formed when Compound T reacts with dilute nitric acid at room temperature while Compound X formed when Compound T reacts with concentrated nitric acid at room temperature. Compound T reacts with Br2 in CS2 to produce Compound Y. Identify the possible structural formulae for compound T to Y and give TWO (2) characteristics of compound T.
The reaction of N−bromosuccinimide with 4−methyl−3−nitroanisole has been reported in the chemical literature. This reaction yields a single product in 95% yield. Identify the product formed from this starting material.
An unknown organic compound P has a molecular formula of CaHi60. P reacts with 2,4- dinitrophenylhydrazine but not with Tollen's reagent. P also reacts with iodine in sodium hydroxide to give yellow precipitate. On reduction, compound P produces a new compound Q. On heating the compound Q with concentrated sulphuric acid produces R which decolourises bromine in tetrachloromethane. Identify P, Q and R. Explain your reasoning. 10.
An optically active monoterpene (compound A) with molecular formula C10H18O undergoes catalytic hydrogenation to form an optically inactive compound with molecular formula C10H20O (compound B). When compound B is heated with acid, followed by reaction with O3 and then with dimethyl sulfide, one of the products obtained is 4-methylcyclohexanone. Give possible structures for compounds A and B.
Compound A of molecular formula C8H14 is reduced by sodium in liquid ammonia to give compound B of molecular formula C8H16. product (Y).Both A and B undergo hydrogenation in the presence of a platinum catalyst to give 2,5-dimethylhexane. Ozonolysis of B with an oxidative workup produces a carboxylic acid of molecular formula C4H8O2. Reaction of B with a peroxyacid gives a chiral C8H14O product, but reaction with bromine gives an achiral C8H14Br2 product. What are the identities of A and B?
Nitromethane is reacted with ethyl prop-2-enoate with EtO-Na+, EtOH 3 equivalents to give the product X(C16). X then reacts with H2/Raney Ni to give the product Y(C14), which in turn reacts with Na to give Z (C12). Indicate which products X, Y and Z are.
Dehydration of 2,2,3,4,4,-pentamethyl-3-pentanol gives two alkenes A and B. Ozonolysis of A gives formaldehyde and 2,2,4,4-tetramethyl-3- pentanone. Ozonolysis of B gave formaldehyde and 3,3,4,4-tetramethyl-2-pentanone. Identify and draw the structures of A and B, and explain how B could be formed in the dehydration reaction.
Compound J, C16H16Br2, is optically active. On treatment with strong base, compounds K and L (each C16H14) are formed; K and L each absorb only 2 equivalents of hydrogen when reduced over a Pd/C catalyst. Compound K reacts with ozone to give phenylacetic acid (C6H5CH2COOH), while similar treatment of L gives 2 products. One product, M, is an aldehyde with formula C7H6O; the other product is glyoxal (CHO)2. Draw the structure of compound L.