Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 10, Problem 10.58AP
Interpretation Introduction
Interpretation:
The structures of compound
Concept introduction:
The replacement or substitution of one
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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.
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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?
Chapter 10 Solutions
Organic Chemistry
Ch. 10 - Prob. 10.1PCh. 10 - Prob. 10.2PCh. 10 - Prob. 10.3PCh. 10 - Prob. 10.4PCh. 10 - Prob. 10.5PCh. 10 - Prob. 10.6PCh. 10 - Prob. 10.7PCh. 10 - Prob. 10.8PCh. 10 - Prob. 10.9PCh. 10 - Prob. 10.10P
Ch. 10 - Prob. 10.11PCh. 10 - Prob. 10.12PCh. 10 - Prob. 10.13PCh. 10 - Prob. 10.14PCh. 10 - Prob. 10.15PCh. 10 - Prob. 10.16PCh. 10 - Prob. 10.17PCh. 10 - Prob. 10.18PCh. 10 - Prob. 10.19PCh. 10 - Prob. 10.20PCh. 10 - Prob. 10.21PCh. 10 - Prob. 10.22PCh. 10 - Prob. 10.23PCh. 10 - Prob. 10.24PCh. 10 - Prob. 10.25PCh. 10 - Prob. 10.26PCh. 10 - Prob. 10.27PCh. 10 - Prob. 10.28PCh. 10 - Prob. 10.29PCh. 10 - Prob. 10.30PCh. 10 - Prob. 10.31PCh. 10 - Prob. 10.32PCh. 10 - Prob. 10.33PCh. 10 - Prob. 10.34PCh. 10 - Prob. 10.35PCh. 10 - Prob. 10.36PCh. 10 - Prob. 10.37PCh. 10 - Prob. 10.38PCh. 10 - Prob. 10.39APCh. 10 - Prob. 10.40APCh. 10 - Prob. 10.41APCh. 10 - Prob. 10.42APCh. 10 - Prob. 10.43APCh. 10 - Prob. 10.44APCh. 10 - Prob. 10.45APCh. 10 - Prob. 10.46APCh. 10 - Prob. 10.47APCh. 10 - Prob. 10.48APCh. 10 - Prob. 10.49APCh. 10 - Prob. 10.50APCh. 10 - Prob. 10.51APCh. 10 - Prob. 10.52APCh. 10 - Prob. 10.53APCh. 10 - Prob. 10.54APCh. 10 - Prob. 10.55APCh. 10 - Prob. 10.56APCh. 10 - Prob. 10.57APCh. 10 - Prob. 10.58APCh. 10 - Prob. 10.59APCh. 10 - Prob. 10.60APCh. 10 - Prob. 10.61APCh. 10 - Prob. 10.62APCh. 10 - Prob. 10.63APCh. 10 - Prob. 10.64APCh. 10 - Prob. 10.65APCh. 10 - Prob. 10.66APCh. 10 - Prob. 10.67APCh. 10 - Prob. 10.68APCh. 10 - Prob. 10.69APCh. 10 - Prob. 10.70AP
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- 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?arrow_forwardGrignard 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.arrow_forwardCompound A of molecular formula C8H₁4 is reduced by sodium in liquid ammonia to give compound 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 C8H₁40 product, but reaction with bromine gives an achiral C8H₁4Br2 product. What are the identities of A and B? 14 A is 2,5-dimethyl-3-hexyne; B is cis-2,5-dimethyl-3-hexene A is 2,5-dimethyl-3-hexyne; B is trans-2,5-dimethyl-3-hexene A is 2,5-dimethyl-1,5-hexadiene; B is 2,5-dimethyl-3-hexyne A is 2,5-dimethyl-2,4-hexadiene; B is cis-2,5-dimethyl-3-hexenearrow_forward
- 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?arrow_forwardIdentify 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).arrow_forwardIdentify 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).arrow_forward
- Treatment of a hydrocarbon A (molecular formula C9H18) with Br2 in the presence of light forms alkyl halides B and C, both having molecular formula C9H17Br. Reaction of either B or C with KOC(CH3)3 forms compound D (C9H16) as the major product. Ozonolysis of D forms cyclohexanone and acetone. Identify the structures of A–D.arrow_forwardExplain this observation: Ethyl 3-phenylpropanoate (C6H5CH2CH2CO2CH2CH3) reacts with electrophiles to afford ortho- and para-disubstituted arenes, but ethyl 3-phenylprop-2-enoate (C6H5CH=CHCO2CH2CH3) reacts with electrophiles to afford meta- disubstituted arenes.arrow_forwardAn unknown compound A (molecular formula C7H14O) was treated with NaBH4 in CH3OH to form compound B (molecular formula C7H16O). Compound A has a strong absorption in its IR spectrum at 1716 cm−1. Compound B has a strong absorption in its IR spectrum at 3600–3200 cm−1. The 1H NMR spectra of A and B are given. What are the structures of A and B?arrow_forward
- Compound A has a formula of C7H1403. A forms yellow precipitate with NaOH/I2 but does not form silver mirror with Tollens' test. When A is subjected to acid catalyzed hydrolysis, B is formed which gives positive Tollen's test. Propose all possible structures for A C1 6arrow_forwardCompound A is first treated with ylide Y and then reacted with Rh and hydrogen gas. Using the spectroscopic data provided, what is the structure of Compound A?arrow_forwardA chiral amine A having the R configuration undergoes Hofmann elimination to form an alkene B as the major product. B is oxidatively cleaved with ozone, followed by CH3SCH3, to form CH2 = O and CH3CH2CH2CHO. What are the structures of A and B?arrow_forward
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