Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 15, Problem 15.70AP
Interpretation Introduction
Interpretation:
The structures of chloroprene and neoprene are to be drawn.
Concept introduction:
The addition reaction the protic acid is added to an asymmetric
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21.) Calculate the enthalpy of hydrogenation of benzene to cyclohexane from the following
reactions
A,H (kJ/mol)
C6H6 (1) + 15/2 02 (g) → 6 CO2 (g) + 3 H20 (1)
C6H12 (1) + 9 02 (g) → 6 CO2 (g) + 6 H20 (1)
H2 (g) + ½ 02 (g) → H2O (1)
-3268
-3920
-285.83
a.) -205 kJ/mol
b.) -1507 kJ/mol
c.) -938 kJ/mol
d.) -366 kJ/mol
An unknown hydrocarbon A with the formula C6H12 reacts with 1 molar equivalent of H2 over a palladium catalyst to give hydrocarbon B. Hydrocarbon A also reacts with OsO4 to give the glycol C. When oxidized with KMnO4 in acidic solution, A gives two fragments. One fragment is propanoic acid, CH3CH2COOH, and the other fragment is ketone D (R2C=O). What are the structures of A, B, C and D? Write all reactions.
5
Isopropylbenzene (C9H12) is commercially produced by Friedel–Crafts alkylation of
compound H with 1-chloropropane in the presence of anhydrous aluminium chloride as a
catalyst. CyH12 can be oxidized with strong oxidizing agent to form compound J.
a)
Draw the structure of H.
b)
Write the chemical reaction of isopropylbenzene to form compound J.
c)
Show the mechanism for the formation of isopropylbenzene (C,H12) from
compound H.
C,H¬B1+ OH¯→ C,H¬OH + NaBr
The rate equation for the hydrolysis of C3H,Br with sodium hydroxide is:
rate = k [C3H»Br] [OH ¯]
a)
Draw the structural formula of C3H¬Br. Explain your answer.
b)
State and show the mechanism of the reaction above.
An alkyl halide E, C5H11B undergoes hydrolysis to form an alcohol F,
CSH120. Alcohol F becomes cloudy immediately when reacted with a Lucas reagent.
c)
(i)
(ii)
Deduce the structures of E and F.
State the type of reaction and propose the mechanism for the conversion of E to F.
d)
Draw the structure of the product formed…
Chapter 15 Solutions
Organic Chemistry
Ch. 15 - Prob. 15.1PCh. 15 - Prob. 15.2PCh. 15 - Prob. 15.3PCh. 15 - Prob. 15.4PCh. 15 - Prob. 15.5PCh. 15 - Prob. 15.6PCh. 15 - Prob. 15.7PCh. 15 - Prob. 15.8PCh. 15 - Prob. 15.9PCh. 15 - Prob. 15.10P
Ch. 15 - Prob. 15.11PCh. 15 - Prob. 15.12PCh. 15 - Prob. 15.13PCh. 15 - Prob. 15.14PCh. 15 - Prob. 15.15PCh. 15 - Prob. 15.16PCh. 15 - Prob. 15.17PCh. 15 - Prob. 15.18PCh. 15 - Prob. 15.19PCh. 15 - Prob. 15.20PCh. 15 - Prob. 15.21PCh. 15 - Prob. 15.22PCh. 15 - Prob. 15.23PCh. 15 - Prob. 15.24PCh. 15 - Prob. 15.25PCh. 15 - Prob. 15.26PCh. 15 - Prob. 15.27PCh. 15 - Prob. 15.28PCh. 15 - Prob. 15.29PCh. 15 - Prob. 15.30PCh. 15 - Prob. 15.31PCh. 15 - Prob. 15.32PCh. 15 - Prob. 15.33PCh. 15 - Prob. 15.34PCh. 15 - Prob. 15.35PCh. 15 - Prob. 15.36PCh. 15 - Prob. 15.37PCh. 15 - Prob. 15.38PCh. 15 - Prob. 15.39PCh. 15 - Prob. 15.40PCh. 15 - Prob. 15.41PCh. 15 - Prob. 15.42APCh. 15 - Prob. 15.43APCh. 15 - Prob. 15.44APCh. 15 - Prob. 15.45APCh. 15 - Prob. 15.46APCh. 15 - Prob. 15.47APCh. 15 - Prob. 15.48APCh. 15 - Prob. 15.49APCh. 15 - Prob. 15.50APCh. 15 - Prob. 15.51APCh. 15 - Prob. 15.52APCh. 15 - Prob. 15.53APCh. 15 - Prob. 15.54APCh. 15 - Prob. 15.55APCh. 15 - Prob. 15.56APCh. 15 - Prob. 15.57APCh. 15 - Prob. 15.58APCh. 15 - Prob. 15.59APCh. 15 - Prob. 15.60APCh. 15 - Prob. 15.61APCh. 15 - Prob. 15.62APCh. 15 - Prob. 15.63APCh. 15 - Prob. 15.64APCh. 15 - Prob. 15.65APCh. 15 - Prob. 15.66APCh. 15 - Prob. 15.67APCh. 15 - Prob. 15.68APCh. 15 - Prob. 15.69APCh. 15 - Prob. 15.70APCh. 15 - Prob. 15.71APCh. 15 - Prob. 15.72APCh. 15 - Prob. 15.73APCh. 15 - Prob. 15.74APCh. 15 - Prob. 15.75APCh. 15 - Prob. 15.76APCh. 15 - Prob. 15.77APCh. 15 - Prob. 15.78APCh. 15 - Prob. 15.79APCh. 15 - Prob. 15.80APCh. 15 - Prob. 15.81APCh. 15 - Prob. 15.82APCh. 15 - Prob. 15.83APCh. 15 - Prob. 15.84APCh. 15 - Prob. 15.85APCh. 15 - Prob. 15.86AP
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- Draw Lewis structures for pyridine and its conjugate acid, the pyridinium ion, C5H5NH+. What are the geometries and hybridizations about the nitrogen atoms in pyridine and in the pyridinium ion?arrow_forwardCompound A is unsaturated hydrocarbon with molecular formula (C6H12) reacted with Br2 in water to form compound B. compound C was produced from the reaction between compound A, sulphuric acid and H2O (g). Compound A undergo hydrogenation to form compound D. Compound E was produced from the reaction of compound A with Br2 in room temperature. Compound A undergo hydrohalogenation in the presences of hydrogen peroxide to form compound F. The reaction between compound F with aqueous sodium hydroxide will form compound G. Compound H was produced when compound F reacts with the aqueous ammonia in ethanol. Compound F also reacts with aqueous sodium cyanide to produce compound I. Draw the possible structural formulae of compounds A, B, C, D, E, F, G, H and I. Give the IUPAC nomenclature of compounds H and I. Distinguish between compound A and D.arrow_forwardWhen cyclopropane is treated with HI, 1-iodopropane is formed. A similar type of reaction does not occur with cyclopentane or cyclohexane. Suggest an explanation for cyclopropane’s reactivity.arrow_forward
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Chapter 4 Alkanes and Cycloalkanes Lesson 1; Author: Linda Hanson;https://www.youtube.com/watch?v=PPIa6EHJMJw;License: Standard Youtube License