Organic Chemistry
Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 13, Problem 21P
Interpretation Introduction

Interpretation:

The reagents required to convert 2,3-dimethyl-1,3-butadiene to the given products are to be provided.

Concept introduction:

舧 Electrophiles are electron-deficient species, which has positive or partially positive charge. Lewis acids are electrophiles, which accept electron pair.

舧 Nucleophiles are electron-rich species, which has negative or partially negative charge. Lewis bases are nucleophiles, which donate electron pair.

舧 Free radical is an atom, molecule, or ion that has an unpaired electron, which makes it highly chemically reactive.

舧 Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction.

舧 Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.

舧 Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.

舧 The reaction in which there is addition of hydrogen molecule is called hydrogenation reaction.

H2/Pt is a reducing agent, which reduces alkynes to alkanes.

舧 Hydrogenation with platinum as a catalyst is used to convert unsaturated carbohydrates to saturated hydrocarbons

舧 Oxidation of alkenes with ozone in the presence of dimethyl sulphate results in the formation of ketones or aldehydes, depending on the orientation and position of the double bond.

舧 Ozonolysis helps convert the carbon–carbon double bonds to carbon–oxygen double bond (carbonyl compounds).

舧 Dimethyl sulfide is used as a reducing agent that decomposes the intermediate formed into the carbonyl group.

舧 Alkenes react with bromine and form alkyl dihalides. The product stereochemistry is dependent on the stereochemistry of the reactant alkene.

舧 The 1,2 – addition of hydrohalogenation (HX) to a diene is the addition of hydrogen to the carbon designated as 1 and halogen to the carbon designated as 2. But the positions of carbons as 1 and 2 are not according to the IUPAC numbering of the molecule but as a conjugated diene. The mechanism is similar with 1,4-addition.

舧 The mechanism of 1,2 addition and 1,4-addition of hydrohalogenation is given below:

Organic Chemistry, Chapter 13, Problem 21P

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11:43 Q1. (a) (c) (d) (b) Two stereoisomers of but-2-ene are formed when 2-bromobutane reacts with ethanolic potassium hydroxide. (i) Explain what is meant by the term stereoisomers. Library Name and outline a mechanism for the reaction of 2-bromo-2-methylpropane with ethanolic potassium hydroxide to form the alkene 2-methylpropene, (CH3)2C=CH₂ Name of mechanism Mechanism (ii) Draw the structures and give the names of the two stereoisomers of but-2-ene. Stereoisomer 1 Name (iii) Name this type of stereoisomerism. Select Name Stereoisomer 2 When 2-bromo-2-methylpropane reacts with aqueous potassium hydroxide, 2-methylpropan-2-ol is formed as shown by the following equation. CH3 H₂C-C-CH3 + KOH Br Page 2 of 14 CH3 H3C-C-CH3 + KBr ОН State the role of the hydroxide ions in this reaction. Write an equation for the reaction that occurs when CH3CH₂CH₂CH₂Br reacts with an excess of ammonia. Name the organic product of this reaction. Equation Name of product 9,284 Photos, 1,166 Videos For You…
Write the structure of the major organic product formed in the reaction of 1-pentene with each of the following: (a) Hydrogen chloride (b) Dilute sulfuric acid (c) Diborane in diglyme, followed by basic hydrogen peroxide (d) Bromine in carbon tetrachloride (e) Bromine in water (f) Peroxyacetic acid (g) Ozone (h) Product of part (g) treated with zinc and water (i) Product of part (g) treated with dimethyl sulfide (CH3)2S
Provide the reagents and solvents (where appropriate) needed to bring about the following transformations. (a) CI (b)

Chapter 13 Solutions

Organic Chemistry

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