Examine the reaction/mechanism provided for the acid-catalyzed dehydration of 2-methyl-2-butanol. Select all the following statements that are correct. OH H OH -OH -OH 2 H2SO4 + 人 6 5 + H₂O The curved arrows shown in the mechanism are not drawn correctly 2-methyl-1-butene is also produced by the dehydration. This dehydration reaction proceeds by an E2 mechanism. Compound 6 is the most stable alkene produced. The curved arrows shown in the mechanism are drawn correctly.

Examine the reaction/mechanism provided for the acid-catalyzed dehydration of 2-methyl-2-butanol. Select all the following statements that are correct. OH H OH -OH -OH 2 H2SO4 + 人 6 5 + H₂O The curved arrows shown in the mechanism are not drawn correctly 2-methyl-1-butene is also produced by the dehydration. This dehydration reaction proceeds by an E2 mechanism. Compound 6 is the most stable alkene produced. The curved arrows shown in the mechanism are drawn correctly.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter10: Alcohols

Section10.8: Oxidation Of Alcohols

Problem 10.12P: -Hydroxyketones and -hydroxyaldehydes are also oxidized by treatment with periodic acid. It is not...

See similar textbooks

Similar questions

Acid-catalyzed hydrolysis of the following epoxide gives a trans diol. CH3 CH3 CH3 НО, НО, H,SO, + H,O HO HO Only this glycol This glycol is is formed. not formed. Of the two possible trans diols, only one is formed. How do you account for this stereoselectivity?
-Hydroxyketones and -hydroxyaldehydes are also oxidized by treatment with periodic acid. It is not the -hydroxyketone or aldehyde, however, that undergoes reaction with periodic acid, but the hydrate formed by addition of water to the carbonyl group of the -hydroxyketone or aldehyde. Write a mechanism for the oxidation of this -hydroxyaldehyde by HIO4.
When warmed in dilute sulfuric acid, 1-phenyl-1,2-propanediol undergoes dehydration and rearrangement to give 2-phenylpropanal. (a) Propose a mechanism for this example of a pinacol rearrangement (Section 10.7). (b) Account for the fact that 2-phenylpropanal is formed rather than its constitutional isomer, 1-phenyl-1-propanone.
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.
All rearrangements we have discussed so far have involved generation of an electron-deficient carbon followed by a 1,2-shift of an atom or a group of atoms from an adjacent atom to the electron-deficient carbon. Rearrangements by a 1,2-shift can also occur following the generation of an electron-deficient oxygen. Propose a mechanism for the acid-catalyzed rearrangement of cumene hydroperoxide to phenol and acetone.
The base-promoted rearrangement of an -haloketone to a carboxylic acid, known as the Favorskii rearrangement, is illustrated by the conversion of 2-chlorocyclohexanone to cyclopentanecarboxylic acid. It is proposed that NaOH first converts the a-haloketone to the substituted cyclopropanone shown in brackets and then to the sodium salt of cyclopentanecarboxylic acid. (a) Propose a mechanism for base-promoted conversion of 2-chlorocyclohexanone to the proposed intermediate. (b) Propose a mechanism for base-promoted conversion of the proposed intermediate to sodium cyclopentanecarboxylate.
Show reasonable mechanisms for the following reaction.
Br2, H3O+ གོ་ཤི་ན་ཤི་ H3C CH3 CH3 CH3 Aldehydes and ketones can be halogenated at their a-position by reaction with Cl₂, Br2, or 12, under acidic conditions. Using Br2 under acidic conditions, an intermediate enol is formed which adds bromine at the a-position. The reaction stops after the addition of one bromine because the electron-withdrawing halogen decreases the basicity of the carbonyl oxygen, making the protonation less favorable. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions :OH :OH Br-Br H3C H3C. Br Br CH₂ H₂ H3C CH3 H3C CH3 2b
Suggest a reasonable series of reagents and reactions conditions to prepare cis-2-methylcyclohexly acetate (A) from trans-2-methylcyclohexanol.
Chloral hydrate is a hypnotic drug known as the "knockout drops". It is a gem-diol and can be prepared from chloral (an aldehyde) via hydration reaction as follows. он H,0 H,O Chloral Chloral hydrate i) Write the mechanism for the formation of chloral hydrate in acidic condition. ii) Hydration is reversible. A gem-diol can eliminate water to regenerate its aldehyde. However, with regards to the above schematic diagram, chloral hydrate is more stable compared to chloral. Give an explanation for this stability.
The following substances can be prepared by a nucleophilic addition reaction between an aldehyde or ketoneand a nucleophile. Identify the reactants from which they were prepared. If the substance is an acetal, identifythe carbonyl compound and the alcohol; if it is an imine or enamine, identify the carbonyl compound and theamine. You do not have to consider stereochemistry. In cases where there is more than one answer, just giveone. Use Grignard reagents when an organometallic reagent is required. Draw the Grignard reagent as acovalent magnesium bromide.
OH of H H H3C- Dess-Martin periodinane provides a means to oxidize a primary alcohol to an aldehyde, while avoiding the use of toxic Cr(VI) compounds. The mechanism involves a reaction similar to the E2 elimination, whereby a C=O double bond is formed with a reduced iodine compound as the leaving group. The reaction occurs in a nonaqueous solvent, CH₂Cl₂, so that the aldehyde product can be recovered. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions AOC XT OAc AcO -OAc & A H3C H H AcO CH3 H -OACH OAC ACO CH3 -OAc H Асӧн ета