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EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
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Question
Chapter 14, Problem 14.45AP
Interpretation Introduction
Interpretation:
The structure of compound A is to be proposed with the help of given information.
Concept introduction:
Ozonolysis is the oxidative cleavage of the double bond, where
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Compound A has the formula C₂H₁9Cl. B is a C₂H19Br compound.
A and B undergo base-promoted E2 elimination to give the same alkene C as the major product as well as different minor products.
C reacts with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2,6-dimethylheptane.
Addition of HCI to C yields A as the major product.
Propose structures for A and B.
• Do not use stereobonds in your answer.
• In cases where there is more than one possible structure for each molecule, just give one for each.
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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?
Compound 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-hexene
Chapter 14 Solutions
EBK ORGANIC CHEMISTRY
Ch. 14 - Prob. 14.1PCh. 14 - Prob. 14.2PCh. 14 - Prob. 14.3PCh. 14 - Prob. 14.4PCh. 14 - Prob. 14.5PCh. 14 - Prob. 14.6PCh. 14 - Prob. 14.7PCh. 14 - Prob. 14.8PCh. 14 - Prob. 14.9PCh. 14 - Prob. 14.10P
Ch. 14 - Prob. 14.11PCh. 14 - Prob. 14.12PCh. 14 - Prob. 14.13PCh. 14 - Prob. 14.14PCh. 14 - Prob. 14.15PCh. 14 - Prob. 14.16PCh. 14 - Prob. 14.17PCh. 14 - Prob. 14.18PCh. 14 - Prob. 14.19PCh. 14 - Prob. 14.20PCh. 14 - Prob. 14.21PCh. 14 - Prob. 14.22PCh. 14 - Prob. 14.23PCh. 14 - Prob. 14.24PCh. 14 - Prob. 14.25PCh. 14 - Prob. 14.26APCh. 14 - Prob. 14.27APCh. 14 - Prob. 14.28APCh. 14 - Prob. 14.29APCh. 14 - Prob. 14.30APCh. 14 - Prob. 14.31APCh. 14 - Prob. 14.32APCh. 14 - Prob. 14.33APCh. 14 - Prob. 14.34APCh. 14 - Prob. 14.35APCh. 14 - Prob. 14.36APCh. 14 - Prob. 14.37APCh. 14 - Prob. 14.38APCh. 14 - Prob. 14.39APCh. 14 - Prob. 14.40APCh. 14 - Prob. 14.41APCh. 14 - Prob. 14.42APCh. 14 - Prob. 14.43APCh. 14 - Prob. 14.44APCh. 14 - Prob. 14.45APCh. 14 - Prob. 14.46APCh. 14 - Prob. 14.47AP
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- 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.arrow_forwardCompound W has molecular formula C₁4H18 and reacts with H₂ to form X. Oxidative cleavage of W with O3 followed by CH3 SCH3 affords Y. What is the structure of W?arrow_forwardTreatment 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_forward
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