Question

In: Chemistry

Draw the product(s) formed by heating the following compound in acidic methanol.

Draw the product(s) formed by heating the following compound in acidic methanol.

Solutions

Expert Solution

Concepts and reason

Transesterification is a reaction process where the ester reacts with the alcohol in acid catalyst and heat to produce a new ester and alcohol. In this process, the ester can be converted into other esters using the alcohol group with an acid catalyst.

Fundamentals

Transesterification: Ester conversion to the other ester in the presence of acid catalyst and heat is known as transesterification.

Acid catalyst protonates the carbonyl oxygen in the ester functional group, which leads to oxonium ion. Then, carbonyl electrons are moved towards the oxonium ion while the alcohol group attacks the positively charged carbon in the carbonyl, leading to the formation of a new ester.

 

From the given ester, the structure is shown below.

The protonation of the ester by acid is as follows.

Alcoholic group (methanol) attacks the carbonyl group and forms tetrahedral intermediate.

The acid protonates given ester to form an oxonium ion. The positive charge on oxonium ion attracts the bonded electron pair towards itself, which causes the attack of the methanol group on the positively charged carbon in the carbonyl group to give the tetrahedral intermediate.

Deprotonating the tetrahedral intermediate is as follows.

Acid/base reaction is a process where protonation occurs at non-carbonyl oxygen to make methoxide ion to methanol as a good leaving group.

The leaving group goes out by electrons' movement from the adjacent oxygen and forms oxonium ion, which leads the ester by deprotonation.

Deprotonating of the oxonium ion as follows.

The complete transesterification reaction

 

The tetrahedral intermediate formed through the methanol attack on the oxonium ion, which is formed through the protonation of the ester by an acid. This tetrahedral intermediate further undergoes acid/base reaction through deprotonating at carbonyl oxygen and protonation at non-carbonyl oxygen. This leads to a new ester by leaving the alcohol group.

 

Complete trans esterification reaction

 

Dr. OWL answered 3 years ago
Next > < Previous

Related Solutions

Draw the organic products formed in the following reaction.
Draw the organic products formed in the following reaction.
Write a balanced equation for the oxidation of methanol with KMnO4 in acidic solution; show how...
Write a balanced equation for the oxidation of methanol with KMnO4 in acidic solution; show how you balanced the reaction using half-reactions.
The following compounds can be formed during the Maillard reaction. For each compound: Compound From Caramelization?...
The following compounds can be formed during the Maillard reaction. For each compound: Compound From Caramelization? (Y/N) Color Aroma/Taste #O’s #N’s #S’s Ring Y/N C=O Y/N Diacetyl 2,4,5-trimethyl thiazole 2-acetyl-3,5-dimethyl pyrazine Difurfuryl sulfide 3-ethyl pyridine Furfural Levulinic acid 1-methyl pyrrole Phenylpyruvic acid 2-thienyl mercaptan
1) Draw the structure of the product formed by addition of vitamin B1 and benzaldehyde. 2)...
1) Draw the structure of the product formed by addition of vitamin B1 and benzaldehyde. 2) Ammonia adds to carbonyl groups but is ineffective as a catalyst for the benzoin condensation. Explain. 3) Write a balanced oxidation-reduction equation for the oxidation of benzoin by ammonium nitrate (the cupric ion catalysis need not to be considered). 4) In the benzil oxidation the initial blue color changes to gren as the reaction proceeds. Why? 5) In dilantin sodium it is the imide...
1) Draw the structure of the product formed by addition of vitamin B1 and benzaldehyde. 2)...
1) Draw the structure of the product formed by addition of vitamin B1 and benzaldehyde. 2) Ammonia adds to carbonyl groups but is ineffective as a catalyst for the benzoin condensation. Explain. 3) Write a balanced oxidation-reduction equation for the oxidation of benzoin by ammonium nitrate (the cupric ion catalysis need not to be considered). 4) In the benzil oxidation the initial blue color changes to gren as the reaction proceeds. Why? 5) In dilantin sodium it is the imide...
Draw the product of 2-methylpropene oxide, methyl lithium, hydronium workup Draw the product of (S)-propene oxide,...
Draw the product of 2-methylpropene oxide, methyl lithium, hydronium workup Draw the product of (S)-propene oxide, sodium cyanide, hydronium workup Draw the product of (R)-propene oxide, LiAlD4 and hydronium workup Draw the product of (S)-propene oxide, LiAlD4, hydronium workup
Draw a hybrid solar water heating system.
Draw a hybrid solar water heating system.
Draw the major alkene product formed from dehydrating the following alcohols? a) 2-methylcyclohexanol b) 2,3-dimethylcyclohexanol c)...
Draw the major alkene product formed from dehydrating the following alcohols? a) 2-methylcyclohexanol b) 2,3-dimethylcyclohexanol c) 1,2,2-trimethylcyclohexanol d) 2,2-dimethylcyclohexanol (hint: consider carbocation shifts)     e) 1,2-cyclohexanediol (hint: consider keto-enol tautomerism)
Draw the major organic product(s) for the following reaction. Multiple products may be drawn in one...
Draw the major organic product(s) for the following reaction. Multiple products may be drawn in one box, in any order. Use an expanded octet around sulfur to avoid formal charges. Draw the major organic product(s) for the following reaction. Multiple products may be drawn in one box, in any order. Use an expanded octet around sulfur to avoid formal charges.
A compound dissolved in methanol and need to remove by distillation because heat is sensitive, a...
A compound dissolved in methanol and need to remove by distillation because heat is sensitive, a person hesitate to rait temp above 0C and instead decide to use vacuum distillaion. What required pressure for pure methanol to boil at this temp?
ADVERTISEMENT
Subjects
ADVERTISEMENT
Latest Questions
ADVERTISEMENT