
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Secondary alcohols are often dehydrated in an E2 reaction to give an
Draw curved arrows to show the movement of electrons in this step of the mechanism.

Transcribed Image Text:CH3
POCl3
pyridine
CH2 OH
H20
CH3
H3C
CH3
Secondary alcohols are often dehydrated in an E2 reaction to give an alkene. Elimination follows Zaitsev's rule to give the more substituted alkene as the major
product. Since the reaction occurs via an E2 mechanism, there is no risk of rearrangement of the carbon skeleton as could possibly occur if the elimination occurred
via an E1 mechanism with a carbocation intermediate
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
Il
CI
CH3 HO
+CI
Cl
H3C
CH3
Нас
CH3
Cl
Retry Entire Group
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While dehydrating 2-Methlycyclohexanol to 1-Methlycyclohexanol, and 3-Methlycyclohexanol
1)what is the common problem associate with E1 reaction? Discuss the intermediate.
2) Briefly compare and contrast E1 vs E2 Elimination reactions. INclude details such as speed of the reactions in relation to each other, rate-determining steps (E1), and stereochemical requirements (E2). Mention whether the steps of the reactions are reversible and discuss the conditions that can drive the equilibrium to favor product formation.
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The following bicyclic ketone has two -carbons and three -hydrogens. When this molecule is treated with D2O in the presence of an acid catalyst, only two of the three -hydrogens exchange with deuterium. The -hydrogen at the bridgehead does not exchange. How do you account for the fact that two -hydrogens do exchange but the third does not? You will find it helpful to build models of the enols by which exchange of -hydrogens occurs.
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Wittig reactions with the following -chloroethers can be used for the synthesis of aldehydes and ketones. (a) Draw the structure of the triphenylphosphonium salt and Wittig reagent formed from each chloroether. (b) Draw the structural formula of the product formed by treating each Wittig reagent with cyclopentanone. Note that the functional group is an enol ether or, alternatively, a vinyl ether. (c) Draw the structural formula of the product formed on acid-catalyzed hydrolysis of each enol ether from part (b).
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-Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the molecular formula C10H16 and a UV absorption maximum at 232 nm. On hydrogenation with a palladium catalyst, 2,6-dimethyloctane is obtained. Ozonolysis of -ocimene, followed by treatment with zinc and acetic acid, produces the following four fragments: (a) How many double bonds does -ocimene have? (b) Is -ocimene conjugated or nonconjugated? (c) Propose a structure for -ocimene. (d) Write the reactions, showing starting material and products.
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2-bromo-2-methylbutane undergoes hydrolysis reaction with water, H2O toform compound W. Compound X and compound Y are produced when 2-bromo-2-methylbutane undergoes elimination reaction with alcoholic ofsodium hydroxide, NaOH.
(ii) What is the type of reaction involved in the formation of compound W?
(iii) Identify the major product of the elimination reaction between compound Xand compound Y based on Zaitsev’s rule.
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Which one of the statements below is wrong about Zaitsev’s Rule.
a.
None of the above
b.
The Zaitsev’s Rule demonstrate the principle of regioselectivity in elimination reactions
c.
The more substituted alkene is the major product of E1 or E2 elimination
d.
The more substituted alkane product is obtained when a proton is removed from β-carbon that is bonded to the fewest hydrogens
e.
The most stable alkene is generally the major product
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Give the structure of the major product formed in each case when the reactant or reactants shown undergo alkene metathesis in the presence of an appropriate ruthenium catalyst.
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Show how to prepare each alkyne from the given starting material. In part (c), D indicates deuterium. Deuterium-containing reagents such as BD3, D2O, and CH3COOD are available commercially.
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Give reasons for the following:
(i) Benzyl chloride is highly reactive towards the SN1 reaction.
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(iii) Electrophilic reactions in haloarenes occur slowly.
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Given that an E2 reaction proceeds with anti periplanar stereochemistry, draw the products of each elimination. The alkyl halides in (a) and (b) are diastereomers of each other. How are the products of these two reactions related? Recall from Section 3.2A that C6H5 −is a phenyl group, a benzene ring bonded to another group.
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Ethers can often be prepared by SN2 reaction of alkoxide ions, RO*, with alkyl halides. Which of the two possible routes would be the better choice to synthesize the molecule shown below? Explain briefly.
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The compound shown below can be synthesised by the reaction of alkyl halide and an alkoxide in the Williamson ether synthesis via an SN2 mechanism. Identify the reagents required and use the plausible mechanism to show the product formation. Also look at the combination of alkyl halide and alkoxide chosen and explain whether or not a good yield of the product is expected.
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