Chapter 12, Problem 35P

Interpretation Introduction

Interpretation:

The route to convert given starting materials into final products is to be provided.

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 which 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 to alcohols. The reaction of cyanides with RMgX forms ketones. It reacts with carbon dioxide to form carboxylic acid.

Treatment of alcohol bearing beta hydrogen forms alkene, on heating with sulfuric acid.

Alkenes form cis-diols on reaction with potassium permanganate while they form trans-diols by epoxidation with mCPBA (metachloroperbenzoic acid)

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.

Cyclohexanone reacts with methylmagnesium bromide to form $1-\text{methyl cyclohexan}-1-\text{ol}$.

The secondary alcohol is treated with concentrated acid to form an alkene.

Alkene on reaction with mCPBA forms epoxide which on acidic hydrolysis forms $trans-\text{diol}$.

Butyrolactone reacts with an excess of ethyl magnesium bromide to form a diol with one secondary and one primary alcohol.

The primary alcohol is oxidized into the aldehyde by PCC.

Benzaldehyde reacts with $\text{hex}-5-\text{ene}$ magnesium bromide to form a secondary alcohol. On treating the formed product with diborane in the presence of peroxide in basic medium forms a primary alcohol.