Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Textbook Question
Chapter 11.8, Problem 10P
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.
Criteria for satisfactory score
Reactants, products, and reagents that complete a reaction scheme must specific compounds, not generic categories.
Reagents and structures must be valid Lewis structures.
Tasks
1. Complete the synthetic sequences by drawing products/substrates/reagents in empty spaces in reactions below.
2. Draw the mechanism of tautomerization (line 3).
Chapter 11 Solutions
Organic Chemistry (6th Edition)
Ch. 11.1 - Problem 11.1 Neopheliosyne B is a novel acetylenic...Ch. 11.2 - Give the IUPAC name for each compound.Ch. 11.2 - Give the structures corresponding to each of the...Ch. 11.3 - Prob. 4PCh. 11.5 - Prob. 5PCh. 11.6 - Which bases can deprotonate acetylene? The pKa...Ch. 11.7 - Draw the organic products formed when each alkyne...Ch. 11.7 - Draw additional resonance structures for each...Ch. 11.8 - Problem 11.9 Draw the products formed when is...Ch. 11.8 - Explain the following result. Although alkenes...
Ch. 11.9 - Problem 11.11 Draw the keto tautomer of each...Ch. 11.9 - Prob. 12PCh. 11.9 - a Draw two different enol tautomers of...Ch. 11.10 - Prob. 14PCh. 11.10 - Problem 11.15 Draw the organic products formed in...Ch. 11.11 - Problem 11.16 What acetylide anion and alkyl...Ch. 11.11 - Problem. 11.17 Show how , and can be used to...Ch. 11.11 - Prob. 18PCh. 11.11 - Draw the products of each reaction. a. b.Ch. 11.11 - Prob. 20PCh. 11 - Prob. 25PCh. 11 - 11.25 Answer the following questions about...Ch. 11 - 11.26 Give the IUPAC name for each alkyne.
a. ...Ch. 11 - Prob. 28PCh. 11 - Which of the following pairs of compounds...Ch. 11 - Prob. 30PCh. 11 - 11.30 How is each compound related to A? Choose...Ch. 11 - Prob. 32PCh. 11 - 11.33 Draw the products formed when is treated...Ch. 11 - What reagents are needed to convert (CH3CH2)3CCCH...Ch. 11 - 11.36 What alkynes give each of the following...Ch. 11 - 11.37 What alkyne gives each compound as the only...Ch. 11 - 11.38 Draw the organic products formed in each...Ch. 11 - 11.42 What reactions are needed to convert alcohol...Ch. 11 - 11.50 What acetylide anion and alkyl halide are...Ch. 11 - 11.52 Devise a synthesis of each compound using ...Ch. 11 - Prob. 58PCh. 11 - 11.59 N-Chlorosuccinimide (NCS) serves as a source...Ch. 11 - 11.60 Draw a stepwise mechanism for the following...Ch. 11 - 11.61 Draw a stepwise mechanism for the following...
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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 products (including stereoisomers) formed when 2- methylhex-2-ene is treated with HBr in the presence of peroxides.arrow_forwarddraw the two possible carbocations that can form when this alkene reacts with a strong acid (such as HBr or H3O+). of the two structures you drew, circle the more stable carbocationarrow_forward
- 4. What are the products obtained from the following elimination reaction? Indicate the major product. CH3 CH,CH,ČCH, H2O 5. a) Determine the major product that is formed when the alkyl halide reacts with a hydroxide ion in an elimination reaction. CH;CH,CH,CH,CCH, Br b) For the major elimination product obtained in 5a), which stereoisomer (cis or trans) is obtained in greater yield? Draw the two isomers and provide the names of the compounds.arrow_forward4. What are the products from the following reaction? H3O+ کاarrow_forward4-pyranone will readily undergo an acid-base reaction. Identify the reaction conditions that will result in the formation of an aromatic product. Then, draw the aromatic resonance product structure. Include all lone pairs in your structure. Ignore inorganic byproducts. H3O+arrow_forward
- Ketones and aldehydes react with sodium acetylide (the sodium salt of acetylene) to give alcohols, as shown in the following example: R1 ОН 1. НС—с: Na* R2 R1 R2 2. Нзо" HC Draw the structure of the major reaction product when the following compound reacts with sodium acetylide, assuming that the reaction takes preferentially from the Si face of the carbonyl group. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • You do not have to explicitly draw H atoms. • If a group is achiral, do not use wedged or hashed bonds on it. CH3 CHarrow_forwardKetones and aldehydes react with sodium acetylide (the sodium salt of acetylene) to give alcohols, as shown in the following example: R, OH 1. HC=C: Na* 2. Hзо C. R2 R2 HC Draw the structure of the major reaction product when the following compound reacts with sodium acetylide, assuming that the reaction takes preferentially from the Re face of the carbonyl group. Use the wedge/hash bond tools to indicate stereochemistry where it exists. You do not have to explicitly draw H atoms. If a group is achiral, do not use wedged or hashed bonds on it.arrow_forwardWhat reaction conditions are needed to convert (R)-2-ethyl-2- methyloxirane to (R)-2-methylbutane-1,2-diol ?arrow_forward
- What reaction conditions are needed to convert (R)-2-ethyl-2-methyloxirane to (S)-2- methylbutane-1,2-diol ?arrow_forwardExplain why the addition of HBr to alkenes A and C is regioselective, forming addition products B and D, respectively.arrow_forwardWhich alkene is the main product of the following reaction? О А.Н.С О B. H с Ос. Н.С H.C H3C H.C H₂C CH3 CH₂ CH3 CH3 H3C H3C OH CH3 cat H₂SO4 Дarrow_forward
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