Identify compounds A, B, and C. a.Compound A has molecular formula C8H12 and reacts with two equivalents of H2. A gives HCOCH2CH2CHO as the only product of oxidative cleavage with O3 followed by CH3SCH3. b.Compound B has molecular formula C6H10 and gives (CH3)2CHCH2CH2CH3 when treated with excess H2 in the presence of Pd. B reacts with NaNH2 and CH3I to form compound C (molecular formula C7H12).

Identify compounds A, B, and C. a.Compound A has molecular formula C8H12 and reacts with two equivalents of H2. A gives HCOCH2CH2CHO as the only product of oxidative cleavage with O3 followed by CH3SCH3. b.Compound B has molecular formula C6H10 and gives (CH3)2CHCH2CH2CH3 when treated with excess H2 in the presence of Pd. B reacts with NaNH2 and CH3I to form compound C (molecular formula C7H12).

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter14: Conjugated Compounds And Ultraviolet Spectroscopy

Section14.SE: Something Extra

Problem 50AP: -Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the...

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Identify compounds A, B, and C. a. Compound A has molecular formula C8H12 and reacts with two equivalents of H2. A gives HCOCH2CH2CHO as the only product of oxidative cleavage with O3 followed by CH3SCH3. b. Compound B has molecular formula C6H10 and gives (CH3)2CHCH2CH2CHCH3 when treated with excess H2 in the presence of Pd. B reacts with NaNH2 and CH3I to form compound C (molecular formula C7H12).
Identify compounds A, B, and C. a.) Compound A has molecular formula C8H12 and reacts with two equivalents of H2. A gives HCOCH2CH2CHO as the only product ofoxidative cleavage with O3 followed by CH3SCH3. b.) Compound B has molecular formula C6H10 and gives(CH3)2CHCH2CH2CH3 when treated with excess H2 in the presence ofPd. B reacts with NaNH2 and CH3I to form compound C (molecularformula C7H12).
Treatment of compound A (C8H17Br) with NaOCH2CH3 affords two constitutional isomers B and C. Ozonolysis of B affords CH2=O and (CH3CH2CH2)2C=O. Ozonolysis of C affords CH3CH2CH2COCH3 and CH3CH2CHO. What is the structure of A?
An unknown compound A of molecular formula C10H18O reacts with H2SO4 to form two compounds (B and C)of molecular formula C10H16. B and C both react with H2 in the presence of Pd-C to form decalin. Ozonolysis of B forms D, and ozonolysis of C forms a diketone E of molecular formula C10H16O2. Identify the structures of compounds A, B, C, and E.
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.
Write out all the isomers of the compound with molecular formula C4H10O Select the normal/ primaryisomer and treat it with conc. H2SO4 and heat. Identify the reaction and give the product ‘A’ from it. Treatment of ‘A’ with HCl/H2O gives ‘B’ Treatment of ‘A’ with cold KMnO4/ -OH gives ‘C’ Treatment of ‘A’ with Hot KMnO4/-OH gives ‘D’ followed by acidification of the mixture to give ‘E’
Treatment of compound A (C8H17Br) with NaOCH2CH3 affords twoconstitutional isomers B and C. Ozonolysis of B affords CH2=O and(CH3CH2CH2)2C=O. Ozonolysis of C affords CH3CH2CH2COCH3 andCH3CH2CHO. What is the structure of A?
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?
2-bromo-2-methylbutane undergoes hydrolysis reaction with water, H2O toform compound W. Compound X and compound Y are produced when 2-bromo-2-methylbutane undergoes elimination reaction with alcoholic ofsodium hydroxide, NaOH. (ii) What is the type of reaction involved in the formation of compound W? (iii) Identify the major product of the elimination reaction between compound Xand compound Y based on Zaitsev’s rule.
-Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the molecular formula C10H16 and a UV absorption maximum at 232 nm. On hydrogenation with a palladium catalyst, 2,6-dimethyloctane is obtained. Ozonolysis of -ocimene, followed by treatment with zinc and acetic acid, produces the following four fragments: (a) How many double bonds does -ocimene have? (b) Is -ocimene conjugated or nonconjugated? (c) Propose a structure for -ocimene. (d) Write the reactions, showing starting material and products.
Oximene and myrcene, two hydrocarbons isolated from alfalfa that have the molecular formula C10H16, both yield 2,6- dimethyloctane when treated with H2 and a Pd catalyst. Ozonolysis of oximene forms (CH3)2C = O, CH2 = O, CH2(CHO)2, and CH3COCHO. Ozonolysis of myrcene yields (CH3)2C = O, CH2 = O, (two equiv), and HCOCH2CH2COCHO. Identify the structures of oximene and myrcene.
An unknown hydrocarbon A with the formula C6H10 reacts with 1 molar equivalent of H2 over a palladium catalyst to give B C6H12 (Rxn 1). Hydrocarbon A also reacts with OsO4 to give the glycol C (Rxn 2). A gives 5-oxohexanal on ozonolysis (Rxn 3). Draw the structures of A, B, and C. Give the reactions.