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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Nucleophilic substitution happens on compounds having nucleophilic
groups as leaving groups. The rule is, the weaker the basicity of a group of
the substrate, the better is its leaving ability. In these substitution
reactions, the basicity of leaving group must be less than the incoming
nucleophilic group. Nucleophilic substitution reaction at sp3-hybridized
carbon is either bimolecular (SN2) or unimolecular. Bimolecular reaction
takes place in single step, involving transition state intermediate. In SN2
reaction, inversion in configuration occurs. In case of optically active alkyl
halides, the inversion in configuration is called Walden inversion. SN2
reaction is preferred if the compound has less steric hindrance. On the
other hand, unimolecular (SN1) reaction involves two steps and a
carbonium ion intermediate. Optically active substrates give racemic
mixture in these type of reactions. Which of the following will produce
enantiomeric pair on treatment with HOH? "
I ÇH,
C,Hs-C-Br…
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*
Two products are possible when pent-2-ene is treated with HBr. Write the structures of the possible products, and explain why they are made in about equal amounts.
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_forwardWhich of the alkynes of molecular formula C5H8 can be prepared in good yield by alkylation or dialkylation of acetylene? Explain why the preparation of the other C5H8 isomers would not be practicalarrow_forwardМЕСНANISMS 1,2-epoxy-1-methylcyclopentane undergoes both acid-catalyzed and base-catalyzed opening of the epoxide ring to form two different products. > Using ethanol as the solvent and an appropriate acid, show the steps in the acid catalyzed mechanism, writing structures for all products of the steps. Circle the major product(s). > Using ethanol as the solvent and an appropriate base, show the steps in the base- catalyzed mechanism, writing structures for all products of the steps. Circle the major product(s). 1,2-epoxy-1-methylcyclopentane CH3arrow_forward
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- 2-Methylhex-3-yne can be prepared by the reaction of an alkynide with an alkyl halide. Does the better synthesis involve alkynide attack on bromoethane or on 2-bromopropane? Explain your reasoning.arrow_forwardX Upon ozonolysis, Compound X produces two compounds: Compound Y and Compound Z. Compound Y can also be prepared from the following synthetic route: PCC 1. R₂BH, THF 1. Mg. Et₂O PCC Compound Y 2. CH₂Cl₂ 2. NaOH, HO CH₂Cl₂ 3. H₂O* From this information, draw the structures of Compounds X, Y, and Z. For Compounds X and Z, different substituents are possible. For grading purposes, just use hydrogens as the substituents. Br مرد →] ►arrow_forwardDo hydration reactions like this one have Markovnikov and anti-Markovnikov products? I know that for addition of halides on alkene double bonds, there are Markovnikov products becasue of 1,2-halide/methyl shifts, but there usually aren't shifts in hydration reactions. Essentially, would the Markovnikov/major product for this reaction have a hydroxy group attached to the tertiary carbocation and the anti-Markovnikov/minor product for this reaction have a hydroxy group attached to the adjacent secondary carbocation?arrow_forward
- When we have discussed the enol-keto tautomerization of ketones in class, the isomerization has been facililated by an acid or base catalyst, with most ketones heavily favoring the carbonyl isomer at equilibrium. However, samples of the ketone below in its pure form (with no acid, base or water present) contain nearly 10% of the enol form! OH -90% -10% From this data, we can infer that the enol isomer of this ketone is particularly stable. Explain the stability of this enol, using terms and ideas that we have discussed in this unit.arrow_forwardWhen 2-bromo-2-methylbutane is treated with a base, a mixture of 2-methyl-2-butene and 2-methyl-1- butene is produced. When potassium hydroxide is the base, 2-methyl-1-butene accounts for 45% of the product mixture. However, when potassium tert-butoxide is the base, 2-methyl-1-butene accounts for 70% of the product mixture. What percent of 2-methyl-1-butene would be in the mixture if potassium propoxide were the base? base Br A. Less than 45% B. C. 45% Between 45% and 70% D. More than 70%arrow_forwardThe carbocation electrophile in a Friedel-Crafts reaction can be generated in ways other than by reaction of an alkyl chloride with AlCl3. For example, reaction of benzene with 2-methylpropene in the presence of H3PO4 yields tert-butylbenzene. Draw a structure for the electrophile.arrow_forward
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