Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 11, Problem 11.63AP
Interpretation Introduction
Interpretation:
The compounds
Concept introduction:
When an allylic alcohol is reacted with enantiomeric tartrate esters,
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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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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.
Compound A has molecular formula C7H15B.. Treatment of compound A with sodium ethoxide yields only one elimination product
(compound B) and no substitution products. When compound B is treated with dilute sulfuric acid, compound C is obtained, which
has molecular formula C7H160. Draw the structures of compounds A, B, and C.
Chapter 11 Solutions
Organic Chemistry
Ch. 11 - Prob. 11.1PCh. 11 - Prob. 11.2PCh. 11 - Prob. 11.3PCh. 11 - Prob. 11.4PCh. 11 - Prob. 11.5PCh. 11 - Prob. 11.6PCh. 11 - Prob. 11.7PCh. 11 - Prob. 11.8PCh. 11 - Prob. 11.9PCh. 11 - Prob. 11.10P
Ch. 11 - Prob. 11.11PCh. 11 - Prob. 11.12PCh. 11 - Prob. 11.13PCh. 11 - Prob. 11.14PCh. 11 - Prob. 11.15PCh. 11 - Prob. 11.16PCh. 11 - Prob. 11.17PCh. 11 - Prob. 11.18PCh. 11 - Prob. 11.19PCh. 11 - Prob. 11.20PCh. 11 - Prob. 11.21PCh. 11 - Prob. 11.22PCh. 11 - Prob. 11.23PCh. 11 - Prob. 11.24PCh. 11 - Prob. 11.25PCh. 11 - Prob. 11.26PCh. 11 - Prob. 11.27PCh. 11 - Prob. 11.28PCh. 11 - Prob. 11.29PCh. 11 - Prob. 11.30PCh. 11 - Prob. 11.31PCh. 11 - Prob. 11.32PCh. 11 - Prob. 11.33PCh. 11 - Prob. 11.34PCh. 11 - Prob. 11.35PCh. 11 - Prob. 11.36PCh. 11 - Prob. 11.37PCh. 11 - Prob. 11.38PCh. 11 - Prob. 11.39PCh. 11 - Prob. 11.40PCh. 11 - Prob. 11.41PCh. 11 - Prob. 11.42PCh. 11 - Prob. 11.43PCh. 11 - Prob. 11.44APCh. 11 - Prob. 11.45APCh. 11 - Prob. 11.46APCh. 11 - Prob. 11.47APCh. 11 - Prob. 11.48APCh. 11 - Prob. 11.49APCh. 11 - Prob. 11.50APCh. 11 - Prob. 11.51APCh. 11 - Prob. 11.52APCh. 11 - Prob. 11.53APCh. 11 - Prob. 11.54APCh. 11 - Prob. 11.55APCh. 11 - Prob. 11.56APCh. 11 - Prob. 11.57APCh. 11 - Prob. 11.58APCh. 11 - Prob. 11.59APCh. 11 - Prob. 11.60APCh. 11 - Prob. 11.61APCh. 11 - Prob. 11.62APCh. 11 - Prob. 11.63APCh. 11 - Prob. 11.64APCh. 11 - Prob. 11.65APCh. 11 - Prob. 11.66APCh. 11 - Prob. 11.67APCh. 11 - Prob. 11.68APCh. 11 - Prob. 11.69APCh. 11 - Prob. 11.70APCh. 11 - Prob. 11.71APCh. 11 - Prob. 11.72APCh. 11 - Prob. 11.73APCh. 11 - Prob. 11.74APCh. 11 - Prob. 11.75APCh. 11 - Prob. 11.76APCh. 11 - Prob. 11.77APCh. 11 - Prob. 11.78APCh. 11 - Prob. 11.79APCh. 11 - Prob. 11.80APCh. 11 - Prob. 11.81AP
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- (S)-2-butanol reacts with potassium dichromate (K2CrO4) in aqueous sulfuric acid to give A(C,HgO). Treatment of A with ethylmagnesium bromide in anhydrous ether gives B(C,H140). Draw the structure of B.arrow_forwardAn achiral hydrocarbon A of molecular formula C7H12 reacts with two equivalents of H2 in the presence of Pd-C to form CH3CH2CH2CH2CH(CH3)2. One oxidative cleavage product formed by the treatment of A with O3 is CH3COOH. Reaction of A with H2 and Lindlar catalyst forms B, and reaction of A with Na, NH3 forms C. Identify compounds A, B, and C. Be sure to answer all parts.arrow_forwardA certain compound of molecular formula C19H38 was isolated from fish oil and from plankton. On hydrogenation it gave 2,6,10,14-tetramethylpentadecane. Ozonolysis gave (CH3)2C O and a 16-carbon aldehyde. What is the structure of the natural product? What is the structure of the aldehyde?arrow_forward
- Compound 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 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_forwardIn the following sequence of reactions which products are identified correctly? Compound A (C 7H 11B1) is treated with magnesium in ether to give B (C 7H 11MgBr), which reacts violently with D 20 to give 1-methylcyclohexene B with acetone (CH 3COCH 3) followed by hydrolysis gives D (C 10H 180). Heating D with with a deuterium atom on the methyl group C. Reaction concentrated H 2SO 4 gives E (C 10H 16), which decolorizes two equivalents of Br 2 to give F (C 10H 16Br 2). E undergoes hydrogenation with excess H 2 and a Pt catalyst to give isobutylcyclohexane. O The correct structure of C is OH O The correct structure of D is O The correct structure of C is Br OI The correct structure of F is 8rarrow_forward
- Sharpless epoxidation of allylic alcohol X forms compound Y. Treatment of Y with NaOH and C6H5SH in an alcohol–water mixture forms Z. Identify the structure of Y and draw a mechanism for the conversion of Y to Z. Account for the stereochemistry of the stereogenic centers in Z. Z has been used as an intermediate in the synthesis of chiral carbohydrates.arrow_forwardCompound A, C₁1 H160, was found to be an optically active alcohol. Despite its apparent unsaturation, no hydrogen was absorbed on catalytic reduction over a Pd/C catalyst. On treatment of A with dilute H₂SO4, dehydration occurred and an optically inactive alkene B, C₁₁H₁4 was produced as the major product. Alkene B, on ozonolysis, gave two products. Product C, C7H6O, was shown to be an aldehyde while product D, C4H8O, was shown to be a ketone. Draw the structure of compound C. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one.arrow_forwardCompound A (C7H11Br) is treated with magnesium in ether to give B (C7H11MgBr) which reacts violently with D2O to give 1-methylcyclohexene with a deuterium atom on the methyl group (C). Reaction of B with acetone (Ch3COCH3) followed by hydrolysis gives D (C10H18O). Heating D with concentrated H2SO4 gives E (C10H16), which reacts with 2 equivalents of Br2 to give F (C10H16Br4). E undergoes hydrogenation with excess H2 and Pt catalyst to give 2-methylpropylcyclohexane. Determine the structures of compounds A through F, and show your reasoning throughout.arrow_forward
- Compound A (C7H11Br) is treated with magnesium in ether to give B (C7H11MgBr), which reacts violently with D2O to give 1-methylcyclohexene with a deuterium atom on the methyl group (C). Reaction of B with acetone (CH3COCH3) followed by hydrolysis gives D (C10H18O). Heating D with concentrated H2 SO4 gives E (C10 H16), which decolorizes two equivalents of Br2 to give F (C10H16 Br4). E undergoes hydrogenation with excess H2 and a Pt catalyst to give isobutylcyclohexane. Determine the structures of compounds A through F, and show your reasoning throughout.arrow_forwardHow many rings and π(pi) bonds are contained in compound A and draw one possible structure for this compound A. Compound A has molecular formula C6H10 and is hydrogenated to a compound having molecular formula C6H12arrow_forwardWhen A is reacted with hot aqueous NaOH, a compound B of molecular formula C8H11NO is produced. With this information, write the correct structure of B and propose the reaction mechanism (step by step, with the correct use of arrows) to obtain B.arrow_forward
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