Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Textbook Question
Chapter 11, Problem 11.11P
Explain the following result. Although
been added.
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CCH
H20, H2SO4
H9SO4
CH3
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
Hjö:
-CH3
-CH3
H3O*
Draw the structure of each product from the reaction of benzene with 2-chloro-1-methylcyclohexane using AlCl 3 as the catalyst and Identify the major product.
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*
Chapter 11 Solutions
Organic Chemistry
Ch. 11 - Draw structures for the three alkynes having...Ch. 11 - Prob. 11.2PCh. 11 - Give the IUPAC name for each compound.Ch. 11 - Give the structures corresponding to each of the...Ch. 11 - Prob. 11.5PCh. 11 - Prob. 11.6PCh. 11 - Which bases can deprotonate acetylene? The pKa...Ch. 11 - Draw the organic products formed when each alkyne...Ch. 11 - Prob. 11.9PCh. 11 - Problem 11.9 Draw the products formed when is...
Ch. 11 - Explain the following result. Although alkenes...Ch. 11 - Problem 11.11 Draw the keto tautomer of each...Ch. 11 - Prob. 11.13PCh. 11 - a Draw two different enol tautomers of...Ch. 11 - Prob. 11.15PCh. 11 - Prob. 11.16PCh. 11 - Prob. 11.17PCh. 11 - Problem. 11.17 Show how , and can be used to...Ch. 11 - Prob. 11.19PCh. 11 - Draw the products of each reaction. a. b.Ch. 11 - Prob. 11.21PCh. 11 - Problem 11.21 Use retrosynthetic analysis to show...Ch. 11 - Prob. 11.23PCh. 11 - Give the IUPAC name for each compound. a. b.Ch. 11 - Prob. 11.25PCh. 11 - 11.25 Answer the following questions about...Ch. 11 - Prob. 11.27PCh. 11 - Give the IUPAC name for each alkyne.Ch. 11 - Prob. 11.29PCh. 11 - Which of the following pairs of compounds...Ch. 11 - Prob. 11.31PCh. 11 - 11.30 How is each compound related to A? Choose...Ch. 11 - Prob. 11.33PCh. 11 - Prob. 11.34PCh. 11 - Prob. 11.35PCh. 11 - 11.33 Draw the products formed when is treated...Ch. 11 - Draw the products formed when 3-hexyne is treated...Ch. 11 - Prob. 11.38PCh. 11 - Prob. 11.39PCh. 11 - What alkynes give each of the following ketones as...Ch. 11 - Prob. 11.41PCh. 11 - 11.37 What alkyne gives each compound as the only...Ch. 11 - Prob. 11.43PCh. 11 - Draw the structure of compounds A-E in the...Ch. 11 - Prob. 11.45PCh. 11 - Prob. 11.46PCh. 11 - 11.42 What reactions are needed to convert alcohol...Ch. 11 - Prob. 11.48PCh. 11 - Prob. 11.49PCh. 11 - 11.45 Explain the following statement. Although ...Ch. 11 - Draw a stepwise mechanism for the following...Ch. 11 - Prob. 11.52PCh. 11 - Prob. 11.53PCh. 11 - Prob. 11.54PCh. 11 - Prob. 11.55PCh. 11 - Synthesize each compound from acetylene. You may...Ch. 11 - Prob. 11.57PCh. 11 - Prob. 11.58PCh. 11 - 11.55 Devise a synthesis of the ketone, , from ...Ch. 11 - 11.56 Devise a synthesis of each compound using ...Ch. 11 - Prob. 11.61PCh. 11 - Prob. 11.62PCh. 11 - 11.60 Draw a stepwise mechanism for the following...Ch. 11 - Draw a stepwise mechanism for the following...Ch. 11 - Prob. 11.65PCh. 11 - Write a stepwise mechanism for each of the...Ch. 11 - Prob. 11.67PCh. 11 - 11.65 Explain why an optically active solution of ...
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- When 2-pentene is treated with Cl2 in methanol, three products are formed. Account for the formation of each product (you need not explain their relative percentages).arrow_forwardDraw the formulas of the reactants and products of the reaction: 2-ethylbutanoyl bromide with excess ethylmagnesium bromide and heating the product with concentrated H2SO4.arrow_forwardWhy is benzene less reactive toward electrophiles than an alkene, even though it has more π electrons than an alkene (six versus two)?arrow_forward
- .Which one of the following molecules can react as electrophile in reactions with alkenes? CH3OH NaCI HCI KCN NaCI O HCI O KCN O CH3OHarrow_forwardGive the major product(s) of the following reaction. Cro;CH OH N.arrow_forwardNitration of an aromatic ring involves an electrophilic substitution reaction. Draw the structure of the electrophile that is attacked by the aromatic ring and the intermediate formed after attachment of the electrophile to the ring. Be sure to show formal charges.arrow_forward
- The reaction of p-cresol with CH2=O resembles the reaction of phenol (PhOH) with CH2=O, except that the resulting polymer is thermoplastic but not thermosetting. Draw the structure of the polymer formed, and explain why the properties of these two polymers are so different.arrow_forwardThe following product can be synthesized from the reaction of an alkene with Hg(OAc)2 followed by reduction with NaBH4. Draw all possible alkenes that will give the product shown.arrow_forwardWhich is the MAJOR product of the following reaction?arrow_forward
- A. In the following reaction, the alkene is acting as a/n + B. In the following reaction, water is acting as a/n CCH3 + H20: HOCHCH3 + H3oarrow_forwardJust to reiterate, the question is to draw out all possible alkene reactants that will result in the shown product.arrow_forwardHydroxylation of E-2-pentene with osmium tetroxide yields a different product than the same reaction using the Z configuration. Draw the structures of the alkenes and show the stereochemistry for each product. Explain any differences between them.arrow_forward
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