Chapter 12, Problem 29P

Interpretation Introduction

Interpretation:

Each of the given compounds starting from primary or secondary alcohols is to be synthesized.

Concept introduction:

Electrophiles are electron deficient species that have positive or partially positive charge. Lewis acids are electrophiles that accept electron pair.

Nucleophiles are electron rich species that have negative or partially negative charge. Lewis bases are nucleophiles that donate electron pair.

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

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.

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

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

The Grignard reagent or RMgX is a polar organometallic reagent that undergoes nucleophilic addition reaction with aldehydes and ketones. It contains organic group that is covalently bonded to magnesium atom, which is also bonded to halogen atom.

Grignard reagent or RMgX can be synthesized from haloalkanes by reacting them with magnesium in the presence of dry ether.

The Grignard reagent or RMgX is a reagent that can be prepared from an alkyl halide and magnesium in the ether. It adds on the alkyl group to the carbonyl moiety and converts aldehydes or ketones into alcohols. The reaction of cyanides with RMgX forms ketones. It reacts with carbon dioxide to form carboxylic acid.

Hydroxyl group of an alcohol can undergo substitution to form halogen derivatives with reagents like MsCl or ${\text{PBr}}_3$.

Primary and secondary alcohols can be oxidized to aldehydes or ketones by oxidizing them with PCC and chromic acid respectively.

The $-\text{OH}$ group is replaced by $-\text{Br}$ on reaction with ${\text{PBr}}_{\text{3}}$.

Alkene is converted into alcohol on reaction with THF and water.

Alkene is converted into alkane in presence of ${\text{H}}_{\text{2}}\text{/Pt, Pd}$ or Ni.

Alcohol can be converted into aldehyde in the presence of DMSO, ${\text{Et}}_{\text{3}}\text{N}$, or PCC. ${\text{CH}}_{\text{2}}{\text{Cl}}_{\text{2}}$

Secondary alcohol can be converted into ketone on reaction with ${\text{H}}_{\text{2}}{\text{CrO}}_{\text{4}}$, acetone and water.

Primary alcohol can be converted into carboxylic acid on reaction with (i) ${\text{KMnO}}_{\text{4}}{\text{,HO}}^{-}$ and heat, (ii) ${\text{H}}_{\text{3}}{\text{O}}^{+}$

Primary alcohol can be converted into ether on reaction with sulfuric acid at ${140}^{°}\text{C}$ .

Grignard reagent reacts with a ketone in the presence of ${\text{NH}}_{\text{4}}{\text{Cl/H}}_{\text{2}}\text{O}$ to form an alcohol.