Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 8, Problem 44P
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Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov
regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called
an enol. The enol immediately rearranges to a more stable ketone via tautomerization.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
-X티
Hö:
H-O
-CH3
-CH3
H30*
NAME and DRAW the STRUCTURE of ALL the alkenes which could
undergo catalytic hydrogenation at 900°C to form methylcyclopentane. Circle the
alkene with the HIGHEST stability and X the alkene with the HIGHEST heat of
hydrogenation. Give reasons for your choice.
f) Alkene X can be decomposed with hydrogen peroxide catalyzed by sodium tungstate to substance Q. This can be further
degraded by iodoform reaction to substance R. Give the structures of substances Q and R.
Xx
S
Na₂WO4
H₂O2
Q
(C9H1603)
1: NaOH, 1₂
2: H+
P₂O5
teplo
- CHI3
R
(C8H1404)
P₂O5
teplo
T
g) The preparation of substance Q from substance X using hydrogen peroxide is a redox reaction.
Identify the reductant and oxidant in this reaction, write the formal oxidation number
to the atoms where it changes during the reaction and calculate the reaction.
h) Substances Q and R undergo a reaction with phosphorous oxide under heating to form
various products T and S. Determine the structure of substances T and S if you know their H NMR :
1H NMR (S): 2.2 (t, 2H); 1.8 (t, 2H); 1.3 (s, 6H).
1H NMR (T): 4.6 (d, 1H); 4.3 (d, 1H); 2.2 (t, 2H); 1.5 (t, 2H); 1.3 (s, 6H).
Chapter 8 Solutions
Organic Chemistry
Ch. 8 - Prob. 1PPCh. 8 - PRACTICE PROBLEM Outline mechanisms for the...Ch. 8 - Practice Problem 8.3 Provide mechanistic...Ch. 8 - Prob. 4PPCh. 8 - PRACTICE PROBLEM
8.5 In one industrial synthesis...Ch. 8 - Prob. 6PPCh. 8 - Prob. 7PPCh. 8 - Prob. 8PPCh. 8 - Prob. 9PPCh. 8 - PRACTICE PROBLEM (a) Outline a likely mechanism...
Ch. 8 - Prob. 11PPCh. 8 - Prob. 12PPCh. 8 - Practice Problem 8.13
Specify the appropriate...Ch. 8 - Prob. 14PPCh. 8 - Practice Problem 8.15 Write a mechanism to explain...Ch. 8 - Prob. 16PPCh. 8 - Prob. 17PPCh. 8 - Prob. 18PPCh. 8 - Practice Problem 8.19 Treating cyclohexene with l,...Ch. 8 - Prob. 20PPCh. 8 - Practice Problem 8.21
Predict the products of the...Ch. 8 - Prob. 22PPCh. 8 - Prob. 23PPCh. 8 - Prob. 24PPCh. 8 - Prob. 25PPCh. 8 - Write structural formulas for the products that...Ch. 8 - Prob. 27PCh. 8 - Prob. 28PCh. 8 - 8.29. Give the structure of the products that you...Ch. 8 - Give the structure of the products you would...Ch. 8 - Prob. 31PCh. 8 - Prob. 32PCh. 8 - Prob. 33PCh. 8 - Prob. 34PCh. 8 - Prob. 35PCh. 8 - Prob. 36PCh. 8 - Prob. 37PCh. 8 - When 3, 3-dimethyl-2-butanol is neared with...Ch. 8 - Prob. 39PCh. 8 - Prob. 40PCh. 8 - Prob. 41PCh. 8 - The reaction of bromine with cyclohexene involves...Ch. 8 - Prob. 43PCh. 8 - Internal alkynes can be isomerized to terminal...Ch. 8 - 8.43. Write a mechanism that explains the...Ch. 8 - 8.44. Write a mechanism for the following...Ch. 8 - Write a mechanism that explains formation of the...Ch. 8 - Prob. 48PCh. 8 - 8.49 Farnesene (below) is a compound found in the...Ch. 8 - Prob. 50PCh. 8 - Limonene is a compound found in orange oil and...Ch. 8 - Prob. 52PCh. 8 - Synthesize the following compound starting with...Ch. 8 - Prob. 54PCh. 8 - Predict features of their IR spectra that you...Ch. 8 - Deduce the structures of compounds A, B, and C,...Ch. 8 - Ricinoleic acid, a compound that can be isolated...Ch. 8 - 8.54. There are two dicarboxylic acids with the...Ch. 8 - Prob. 59PCh. 8 - Prob. 60PCh. 8 - Prob. 61PCh. 8 - Prob. 64PCh. 8 - Prob. 66PCh. 8 - Prob. 62PCh. 8 - Prob. 63PCh. 8 - 8.65
(a)Based on the following information, draw...Ch. 8 - Triethylamine, (C2H5)3N, like all amines, has a...Ch. 8 - (a) Synthesize (3S, 4R)-3,...Ch. 8 - Prob. 2LGPCh. 8 - Prob. 3LGPCh. 8 - Prob. 4LGPCh. 8 - 8.1 A hydrocarbon whose molecular formula is...Ch. 8 - Prob. 2QCh. 8 - Give the major product of the reaction of...Ch. 8 - The compound shown here is best prepared by which...Ch. 8 - 8.5 A compound whose formula is C6H10 (Compound A)...Ch. 8 - Prob. 6QCh. 8 - 8.7 Which reaction sequence converts cyclohexene...Ch. 8 - Which of the following sequences leads to the best...
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- Alcohols are important for organic synthesis, especially in situations involving alkenes. The alcohol might be the desired product, or the OH group might be transformed into another functional group via halogenation, oxidation, or perhaps conversion to a sulfonic ester derivative. Formation of an alcohol from an alkene is particularly powerful because conditions can be chosen to produce either the Markovnikov or non-Markovnikov product from an unsymmetrical alkene. Using your reaction roadmap as a guide, show how to convert 4-methyl-1-pentene into 5-methylhexanenitrile. You must use 4-methyl-1-pentene and sodium cyanide as the source of all carbon atoms in the target molecule. Show all reagents needed and all molecules synthesized along the way.arrow_forwardQuestion 9 of 9 Choose the best set of conditions for a Friedel-Crafts acylation of aromatic compounds. A) CH;C(O)CI, AICI3 B) CH3C(O)CI C) CH;C(O)CI, NaCI D) CH3C(O)CI, Cl2, H2Oarrow_forwardThe oxygen in water is primarily (99.8%) 16O, but water enriched with theheavy isotope 18O is also available. When a ketone or aldehyde is dissolved inH2O, the isotopic label becomes incorporated into the carbonyl group: R2CPO H2O n R2CPO H2O. Explain.arrow_forward
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