III. It is known that the solvolysis of 2-bromo-2-methylbutane in ethanol at 25 produces a mixture of substitution (64% mole) and elimination (36% mole) products. If the same alkyl halide is allowed to undergo solvolysis at the same temperature in tert-butyl alcohol, please predict (qualitatively) how the composition of the mixture will change and rationalize your prediction. You only need to consider nucleophilic substitution and elimination. its)

III. It is known that the solvolysis of 2-bromo-2-methylbutane in ethanol at 25 produces a mixture of substitution (64% mole) and elimination (36% mole) products. If the same alkyl halide is allowed to undergo solvolysis at the same temperature in tert-butyl alcohol, please predict (qualitatively) how the composition of the mixture will change and rationalize your prediction. You only need to consider nucleophilic substitution and elimination. its)

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

Chapter19: Enolate Anions And Enamines

Section: Chapter Questions

Problem 19.40P: Enamines normally react with methyl iodide to give two products: one arising from alkylation at...

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Enamines normally react with methyl iodide to give two products: one arising from alkylation at nitrogen and the second arising from alkylation at carbon. For example, Heating the mixture of C-alkylation and N-alkylation products gives only the product from C-alkylation. Propose a mechanism for this isomerization.
Reaction of -pinene with borane followed by treatment of the resulting trialkylborane with alkaline hydrogen peroxide gives the following alcohol. Of the four possible cis,trans isomers, one is formed in over 85% yield. (a) Draw structural formulas for the four possible cis,trans isomers of the bicyclic alcohol. (b) Which is the structure of the isomer formed in 85% yield? How do you account for its formation? Create a model to help you make this prediction.
The following sequence of steps converts (R)-2-octanol to (S)-2-octanol. Propose structural formulas for intermediates A and B, specify the configuration of each, and account for the inversion of configuration in this sequence.
When 2-iodo-1,4-dimethylcyclohexane is heated in acetic acid, CH3COOH, a mixture of substitution and elimination products is obtained. Provide structures for all possible products, writing [not drawing] the name of the mechanism by which each one is formed.
Write the formula of reagents used in the following reactions:(i) Bromination of phenol to 2,4,6-tribromophenol(ii) Hydroboration of propene and then oxidation to propanol.(b) Arrange the following compound groups in the increasing order of their property indicated:(i) p-nitrophenol, ethanol, phenol (acidic character)(ii) Propanol, Propane, Propanal (boiling point)
Bromine reacts with alkenes in methanol according to the equation: - When this reaction was carried out with 4-tert-butylcyclohexene, only one isomer was formed with the molecular formula C12H23BrO (80% yield). Which of the following is the structure more reasonable for this compound?. Explain your reasoning through acorresponding mechanism.
(a) Give the products of the phosphoric acid-catalyzed dehydration of 2-methylcyclohex-3- enol. Label the three products with major, minor, and trace amounts. OH H3PO4, heat (b) Describe the rule that is applied in the acid-catalyzed dehydration of 2-methylcyclohex-3- enol. Explain your answer based on the products formed.
3-Chloro-2-methylpropene reacts with sodium methoxide in methanol to form 3-methoxy-2-methylpropene. For each of the following changes in the reaction conditions, state whether the reaction rate would increase, decrease, or remain the same. Explain your reasoning. In some cases the identity of the major organic product would be expected to change; in such cases, give the expected major product. (a) the same quantities of reagents are dissolved in half the volume of methanol (b) 3-bromo-2-methylpropene is used in place of 3-chloro-2-methylpropene (c) sodium methanethiolate (CH3SNa) is used in place of of sodium methoxide
Choose from the options A-E and explain briefly by illustrations the chemistry behind each answer. Preamble: A reaction flask contains a 2-bromopentane in an ethanolic solution of sodium ethoxide at room temperature and results in the formation of two olefinic 1.All the following parameters would affect the rate and kinetics of the reaction exceptA.Solvent mediumB.Reaction temperatureC.Reaction timeD.Geometry and structure of the alkyl halideE.pH 2.What would be the major product when 2-iodopentane is involved in a dehydrohalogenation reaction? A.2-iodo-1-penteneB.2-penteneC.(E)-2-penteneD.(Z)-2-penteneE.Cis-2-pentene
(a) For the reaction of 1-methoxy-4-methylbenzene with CH3C(O)CI in the presence of AICI3, describe the bonding and electron distribution in 1-methoxy- 4-methylbenzene, formation and structure of the electrophile in the reaction, and the most stable intermediate responsible for the end product. i H3C1 CI, AICI 3 Me- -OMe 1-methoxy-4-methylbenzene (b) Use phenol as the substrate, propose a synthetic scheme to produce 2-allyl-4-bromophenol (Mechanism not required). Br OH OH phenol 2-allyl-4-bromophenol (c) Propose a synthesis of Compound A starting from benzaldehyde and other necessary reagents of your choice (Mechanism not required). OH CHO CI. Compound A benzaldehyde (d) For the given 13C NMR chemical shifts of the carbonyl carbons in the order of ketones > aldehydes > carboxylic acids, provide an explanation. O CH3 H3C. 13C NMR Chemical Shifts: H₂C1 H₂C H > OH 200 ppm 181 ppm 209 ppm
Under strongly acidic conditions, hexane is observed to undergo an isomerization process, during which it is converted into branched alkanes having the same molecular formula as hexane (C6H₁4). The rate at which each constitutional isomer is produced is related to the type of acid that is used in the reaction and the degree of mixing that occurs during the reaction (J. Chem. Soc., Perkins Trans. 2 1999, 12, 2715-2718). Step 1 Draw a bond-line structure of hexane. Draw Your Solution There are four branched isomers of hexane. Draw bond-line structures of all four of its isomers. Draw Your Solution
Optically active (R)-2-bromobutane can be converted to 2-butanol under either conditions A or conditions B. Describe the stereochemistry of the product solutions for the two different conditions.