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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Students have asked these similar questions
Provide the reagents and solvents (where appropriate) needed to bring about the following transformations. (a) CI (b)
Write the structure of the major organic product formed in the reaction of each of the following with hydrogen bromide in the absence of peroxides and in their presence. (a) 1-Pentene (b) 2-Methyl-2-butene (c) 1-Methylcyclohexene
Draw a structural formula for the alcohol formed by treating each alkene with borane in tetrahydrofuran (THF) followed by hydrogen peroxide in aqueous sodium hydroxide, and specify stereochemistry where appropriate. (a) (d) (b) (e) (c)

Chapter 13 Solutions

Organic Chemistry

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