Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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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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