Question

The product of the reaction of ethyl orthoformate, $HC{(OEt)_3}$ with one equivalent of $C{H_2}MgBr$ followed by hydrolysis would be
A. $C{H_3}CH{(OEt)_2}$
B. $C{H_3}CHO$
C. $C{H_3}C{(OEt)_3}$
D. No reaction takes place

Answer 1

Hint: Triethyl orthoformate is an organic compound with the molecular formula $HC{(OEt)_3}$ or $HC{(O{C_2}{H_5})_3}$ and is used in the Bodroux-Chichibabin aldehyde synthesis to produce acetaldehyde.

Complete Step by step answer: Triethyl orthoformate is an organic compound with the molecular formula $HC{(OEt)_3}$ or $HC{(O{C_2}{H_5})_3}$ . It is a colourless volatile liquid and the orthoester of formic acid and is commercially available. The industrial synthesis is from hydrogen cyanide and ethanol. It may be prepared from the reaction of sodium ethoxide and chloroform. It is used in the Bodroux-Chichibabin aldehyde synthesis as given below.

$RMgBr + HCl{(O{C_2}{H_5})_3} \to RC(H){(O{C_2}{H_5})_2} + MgBr(O{C_2}{H_5}) \to ROH$

Triethyl orthoformate is an excellent reagent for converting compatible carboxylic acids to ethyl esters. Alternatively, added to ordinary esterification using catalytic acid and ethanol. TEOF helps drive esterification to completion by converting the by-product water formed to ethanol and ethyl formate.
The Bodroux-Chichibabin aldehyde synthesis is a chemical reaction whereby a Grignard reagent is converted to an aldehyde one carbon longer. The general formula of output is $ROH$ and the option matching this general form is option b which is $C{H_3}CHO$.

Therefore, the correct answer is option B.

Additional Information: The output formed in the above reaction is $C{H_3}CHO$ which is also known as acetaldehyde also known by its systematic name as ethanal is an organic chemical compound which is sometimes abbreviated as $MeCHO$ . It is one of the most important aldehydes occurring widely in nature and being produced on a large scale in industry. It occurs naturally in coffee, bread and ripe fruit.

Note: Triethyl orthoformate is an organic compound with the molecular formula $HC{(OEt)_3}$ or $HC{(O{C_2}{H_5})_3}$ and is used in the Bodroux-Chichibabin aldehyde synthesis to produce acetaldehyde having molecular formula $C{H_3}CHO$ and with general formula $ROH$ .