Show how you would accomplish the following synthetic conversions

(a)

(b)

(c)

(d)

Short Answer

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(a)

(b)

(c)

(d)

Step by step solution

01

(a): Synthetic compound

A compound is synthesized by a chemical reaction rather than arising naturally.These types of compounds have control by humans in any chemical reaction.

Phenol is a cyclic organic compound that contains one hydroxyl group.

02

Conversion

Phenol reacted with sodium forms an intermediate which in reaction with bromomethyl forms ethyl phenyl ether.

Formation of ethyl phenyl ether

03

(b) : Toluene

Toluene is an aromatic compound that contains a methyl group attached to the phenyl. It is colourless and used in oil refining, and paints.

04

Conversion

2 moles of Toluene-2-bromomethyl treated with sodium hydroxide forms respective alcohol. Then treated with 1 equivalent of sodium hypochlorite form aldehyde, then hydrolyzed and treated with sulfuric acid form 1-methyl-2-[2-(2-methylphenyl)ethyl]benzene.

Formation of 1-methyl-2-[2-(2-methylphenyl) ethyl] benzene

05

(c): Bromobenzene

Bromobenzene is an aromatic compound that is a colourless liquid and acts as a reagent. Bromine is attached to the benzene. Used as solvent.

06

Conversion

Bromobenzene was treated with bromo magnesio benzene, then treated with butan-1-al followed by hydrolysis from respective alcohol. Then finally treated with form cyclopentan-1-butanone.

Formation of cyclopentan-1-butanone

07

(d):Cyclohexan-1-methanol

Cyclohexan-1-methanol is an aromatic compound that contains a methyl alcohol group.

08

Conversion

Cyclohexan-1-methanol treated with 1 equivalent of form cyclohexan-1-al, which on further reaction with bromo magnesio ethyl form cyclohexan-1-propanol.

Formation of cyclohexan-1-propanol

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Most popular questions from this chapter

We have covered several oxidants that use a multi-valent atom (Cr, Cl, S, or I) as their active species, going from a higher oxidation state before the oxidation to a lower oxidation state after oxidizing the alcohol. Draw the structure of the following atoms, before and after the oxidation of an alcohol to a ketone or aldehyde. How many bonds to oxygen does each atom have before and after the oxidation?

(a) the Cr in chromic acid

(b) the Cl in sodium hypochlorite

(c) the S in the Swern oxidation

(d) the I in the DMP reagent

(e)the carbinol C in the alcohol that is oxidized.

Trichloroisocyanuric acid, TCICA, also known as “swimming pool chlorine,” is a stable solid that oxidizes alcohols, following a mechanism similar to oxidation by HOCl. No reaction occurs between TCICA and the alcohol (in a solvent such as acetonitrile) until one drop of HCl(aq) is added, whereupon the reaction is over in a few minutes. Write the mechanism for this oxidation that shows the key role of the acid catalyst. Show the oxidation of just one alcohol, not three. (Hint: The carbonyls are the most basic sites on TCICA.)

Show the alcohol and the acid chloride that combine to make the following esters.

(a)

(b)

(c)

(d)

Predict the esterification products of the following acid/alcohol pairs.

(a) CH3CH2COOH + CH3OH

(b) CH3CH2OH + HNO3

(c) 2CH3CH2CH2OH + H3PO4

(d)

(e)

The following reaction involves a starting material with a double bond and a hydroxyl group, yet its mechanism resembles a pinacol rearrangement. Propose a mechanism, and point out the part of your mechanism that resembles a pinacol rearrangement.

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