EBK ORGANIC CHEMISTRY STUDY GUIDE AND S
6th Edition
ISBN: 9781319385415
Author: PARISE
Publisher: VST
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Chapter 10, Problem 10.57AP
Interpretation Introduction
Interpretation:
The compounds
Concept introduction:
The conversion of an alcohol to
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Compound A has the molecular formula C14H25Br and was obtained by reaction of sodium acetylide (HC≡CNa) )with 1,12-dibromododecane. On treatment of compound A with sodium amide, it was converted to compound B (C14H24). Ozonolysis of compound B gave the diacid HO2C(CH2)12CO2H. Catalytic hydrogenation of compound B over Lindlar palladium gave compound C (C14H26), while hydrogenation over platinum gave compound D (C14H28). Sodium-ammonia reduction of compound B gave compound E (C14H26). Both C and E yielded O═CH(CH2)12CH═O on ozonolysis. Assign structures to compound A through E so as to be consistent with the observed transformations.
5. Compound A, C 10H 18O, undergoes reaction with dilute H 2SO 4 at 50 °C to yield a mixture of two alkenes, C 10H 16. The major alkene B, gives only cyclopentanone after ozone treatment followed by reduction with zinc in acetic acid. Which of the following reactions are correct.
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.
Chapter 10 Solutions
EBK ORGANIC CHEMISTRY STUDY GUIDE AND S
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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- Compound A and compound B both have molecular formula C6H12. Both compounds produce epoxides when treated with a peroxy acid (RCO3H). The epoxide resulting from compound A was treated with aqueous acid (H3O+) and the resulting diol has no chiral centers. Identify the two possible structures for compound A (enter two numbers separated by commas with no spaces, e.g. "1,2") The epoxide resulting from compound B was treated with (H3O*) and the resulting diol was a meso compound. Identify compound B 2 3 potn 7 1 5 6 4 8arrow_forwardCompound 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.arrow_forwardOn treatment with Cl2/hν, a compound with the formula C9H12 yields only a single monochloride. What is a possible structure of the compound?arrow_forward
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- A compound of unknown structure (Compound A) is determined by elemental analysis to have a molecular formula of C10H12. Upon reaction with H2 and Pd/CacO3 the unknown absorbs one mole equivalent of hydrogen gas. Upon reaction with ozone, followed by zinc/acetic acid a product with structure shown is obtained. Four possibilities are given for the structure of Compound A. Select the correct answer. HO,C B A D В Both B and C are correct O o o o oarrow_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_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 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_forward
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