Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 12.9, Problem 8P
As measured by their first-order rate constants, the compound shown (
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D. When the alkyl bromides (listed here) were subjected to hydrolysis in a mixture of
ethanol and water (80% EtOH/20% H20) at 55 °C, the rates of the reaction showed the
following order:
(CH3);CBr > CH3Br > CH;CH;Br > (CH3);CHBr
Provide an explanation for this order of reactivity.
b) Listed below are several hypothetical nucleophilic substitution reactions.
None is synthetically useful because the product indicated is not formed at an
appreciable rate. In each case provide an explanation for the failure of the
reaction to take place as indicated.
OMe
HO
+ OMe
+ OH
HO
+ CH;
OH
9. (a) Under certain conditions, the reaction of 0.5 M 1-bromobutane with 1.0 M sodium
methoxide forms 1-methoxybutane at a rate of 0.05 mol/L per second. What would be the
rate if 0.1 M 1-bromobutane and 2.0 M NaOCH3 were used?
(b) Consider the reaction of 1-bromobutane with a large excess of ammonia (NH3). Draw
the reactants, the transition state, and the products. Note that the initial product is the salt
of an amine (RNH* Br) which is deprotonated by the excess ammonia to give the amine.
(c) Show another SN2 reaction using a different combination of an alkoxide and an alkyl
bromide that also produces 1-methoxybutane.
Chapter 12 Solutions
Organic Chemistry - Standalone book
Ch. 12.2 - Write structural formulas for toluene (C6H5CH3)...Ch. 12.3 - Prob. 2PCh. 12.5 - Prob. 3PCh. 12.5 - Prob. 4PCh. 12.6 - Prob. 5PCh. 12.6 - Chrysene is an aromatic hydrocarbon found in coal...Ch. 12.8 - Prob. 7PCh. 12.9 - As measured by their first-order rate constants,...Ch. 12.9 - Give the structure of the principal organic...Ch. 12.9 - Prob. 10P
Ch. 12.10 - Prob. 11PCh. 12.11 - Prob. 12PCh. 12.12 - Prob. 13PCh. 12.13 - Prob. 14PCh. 12.13 - Prob. 15PCh. 12.15 - The regioselectivity of Birch reduction of...Ch. 12.16 - Prob. 17PCh. 12.17 - Both cyclooctatetraene and styrene have the...Ch. 12.17 - Prob. 19PCh. 12.18 - Give an explanation for each of the following...Ch. 12.19 - Prob. 21PCh. 12.19 - What does a comparison of the heats of combustion...Ch. 12.20 - Prob. 23PCh. 12.20 - Prob. 24PCh. 12.20 - Prob. 25PCh. 12.20 - Prob. 26PCh. 12.20 - Prob. 27PCh. 12.20 - Prob. 28PCh. 12.21 - Prob. 29PCh. 12.21 - Prob. 30PCh. 12.22 - Prob. 31PCh. 12.22 - Prob. 32PCh. 12 - Write structural formulas and give the IUPAC names...Ch. 12 - Prob. 34PCh. 12 - Prob. 35PCh. 12 - Prob. 36PCh. 12 - Prob. 37PCh. 12 - Acridine is a heterocyclic aromatic compound...Ch. 12 - Prob. 39PCh. 12 - Prob. 40PCh. 12 - Prob. 41PCh. 12 - Evaluate each of the following processes applied...Ch. 12 - Prob. 43PCh. 12 - Prob. 44PCh. 12 - Prob. 45PCh. 12 - Prob. 46PCh. 12 - Anthracene undergoes a DielsAlder reaction with...Ch. 12 - Prob. 48PCh. 12 - Prob. 49PCh. 12 - The relative rates of reaction of ethane, toluene,...Ch. 12 - Both 1,2-dihydronaphthalene and...Ch. 12 - Prob. 52PCh. 12 - Prob. 53PCh. 12 - Prob. 54PCh. 12 - Prob. 55PCh. 12 - Prob. 56PCh. 12 - Each of the following reactions has been described...Ch. 12 - Prob. 58PCh. 12 - A compound was obtained from a natural product and...Ch. 12 - Prob. 60PCh. 12 - Suggest reagents suitable for carrying out each of...Ch. 12 - Prob. 62PCh. 12 - Prob. 63DSPCh. 12 - Prob. 64DSPCh. 12 - Prob. 65DSPCh. 12 - Prob. 66DSP
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- If the rate of reaction of [0.1 M] sodium cyanide with [0.1 M] 2-bromo-2-methylpropane is 1.2 mole/second, what would be the effect on theoverall rate if the concentration of sodium cyanide is increased to [0.2 M] and the concentration of the alkyl bromide is decreased to [0.05 M]?arrow_forwardList the following in increasing order of nucleophilic strength. CH3COO-, H2O, CH3O-, OH-, CH3CH20-arrow_forwardA student adds NBS to a solution of 1-methylcyclohexene and irradiates the mixture with a sunlamp until all the NBS has reacted. After a careful distillation, the product mixture contains two major products of formula C7H11Br. (a) Draw the resonance forms of the three possible allylic free radical intermediates.arrow_forward
- A chemist needs an ether to use as a solvent for a reaction and wants to synthesize it in one step from two of the following available reagents: sodium ethoxide, bromomethane, potassium tert-butoxide, and 2-bromo-2-methylpropane. i) Which combination(s) will give a good yield of an ether? Illustrate, showing the mechanism of the reaction. ii) Illustrate with a mechanism the reaction of one of the combinations that will not yield an ether?arrow_forwardWhen the alkyl bromides (listed here) were subjected to hydrolysis in a mixture of ethanol and water (80% EtOH/20% H2O) at 55 °C, the rates of the reaction showed the following order: (CH3)3CBR > CH3Br > CH3CH2Br > (CH3)2CHBR Provide an explanation for this order of reactivity.arrow_forwardThe reaction of 2-bromopropane and sodium ethoxide in ethanol reacts 6.7 times 1). faster than 2-bromo-1-deuteriopropane under the same conditions. Explain what mechanism this data is consistent with, and why. H(D) ELOH Br 2) the following reactions. Explain the reason(s) for the difference in relative rates and regiochemistry in Fast Slow EtO EtO ETOH ETOHarrow_forward
- Identify compounds A and B from the following reaction sequence LINH lig MeO 0 (Ozone) MeOH Me₂S Barrow_forwardBr Brz CH3 CH3 H3C CH2CI2 H3C Br Electrophilic addition of bromine, Br2; to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl). In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br: :Br: .CH3 H3C H3C CH3 Br:arrow_forwardwhat structure show the transition state for the rate determining step in the sn1 reaction with this picture?arrow_forward
- Write the appropriate reagents, conditions and products for the following transformations, in a single step. OH II HNO, ? (1) H,SO,arrow_forwardSuggest a reasonable mechanism for the reaction shown Br here. HO CH;CH,OHarrow_forwardThe following reaction involves two sequential Heck reactions. Draw structural formu- las for each organopalladium intermediate formed in the sequence and show how the final product is formed. Note from the molecular formula given under each structural formula that this conversion corresponds to a loss of H and I from the starting material. Acetonitrile, CH,CN, is the solvent. 1% mol Pd(OAc), 4% mol Ph,P CH,CN C4H171 C4H16arrow_forward
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Chapter 4 Alkanes and Cycloalkanes Lesson 2; Author: Linda Hanson;https://www.youtube.com/watch?v=AL_CM_Btef4;License: Standard YouTube License, CC-BY
Chapter 4 Alkanes and Cycloalkanes Lesson 1; Author: Linda Hanson;https://www.youtube.com/watch?v=PPIa6EHJMJw;License: Standard Youtube License