Essential Organic Chemistry, Global Edition
Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 6.2, Problem 3P

(a)

Interpretation Introduction

Interpretation:

For the given set of species the available σ bond orbitals for overlap with vacant p orbital has to be determined.

Concept introduction:

Nucleophile: Nucleophiles are electron rich compounds which donates electrons to electrophilic compounds which results in bond formation.

Nucleophilic nature depends on the negative charge present in the molecule, the solvent in which it present and the electronegativity of the atom.

Electrophile: Electrophiles are electron deficient compounds which accepts electrons from nucleophiles that results in bond formation.

Leaving group: it is a fragment that leaves substrate with a pair of electrons via heterolytic bond cleavage.

Chemical reaction involves bond making and breaking of two or more reactants in order to attain products from the reactants.

Cation: The positively charged chemical species is referred as cation.

(b)

Interpretation Introduction

Interpretation:

From the given carbocation the most stable one has to be identified.

Concept introduction:

Nucleophile: Nucleophiles are electron rich compounds which donates electrons to electrophilic compounds which results in bond formation.

Nucleophilic nature depends on the negative charge present in the molecule, the solvent in which it present and the electronegativity of the atom.

Electrophile: Electrophiles are electron deficient compounds which accepts electrons from nucleophiles that results in bond formation.

Cation: The positively charged chemical species is referred as cation.

Carbocation stability order:

Essential Organic Chemistry, Global Edition, Chapter 6.2, Problem 3P

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Br2 ? How many moles of Br are required to completely halogenate the alkene? A. Three moles B. Four moles C. Two moles D. One mole What is the expected arrangement of the bromine atoms relative to each other among the carbon involved in pi bonding? A. trans-configuration B. anti-conformation C. cis-configuration D. syn-conformation What happens to bromine when it is adjacent to an alkene during a chemical reaction? A. Bromine becomes polarized. B. Bromine becomes acidic. C. Bromine becomes hybridized. D. Bromine becomes stable. The relative arrangement of bromine atoms in the product is primarily due to: A. Hydrogen bonding B. Electronegativity C. Atomic weight D. Repulsion What is your observation after the reaction? A. Bromine water decolorizes. B. A brown precipitate forms. C. The alkene becomes denser. D. A yellow flame is produced.
a. How many s bond orbitals are available for overlap with the vacant p orbital in 1. the isobutyl cation? 2. the n-butyl cation? 3. the sec-butyl cation? b. Which of the carbocations in part a is most stable?
2. For the following nucleophilic substitution reaction: NaOC(CH3)3 CH3 'CH3 CH3 a. Draw the first transition state (TS1), the reaction intermediate, and the second m transition state (TS2) in the labeled boxes. Make sure to show any formal charges, unfilled p-orbitals, and correct stereochemistry. TS₁ 41001 Intermediate ogmos TS2 amond- b. Which of three molecules you drew for part 'a' is lowest in energy? Write your answer in the box below. c. Draw the product(s) of the nucleophilic addition reaction shown. Make sure to use wedged and dashed lines to clearly show the resulting stereochemistry at each chiral center. If there is more than one possible product, draw one in each box - if not, leave one box blank. CH3 Br + NaOC(CH3)3

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Essential Organic Chemistry, Global Edition

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