A compound, HOCH2CH2CH2CH2COCl, reacts with itself to give a new compound. Give the IUPAC name for the starting compound, draw the mechanism for the formation of the new compound and give the prominant feature of the IR spectrum of the new compound.

This compound is highly unstable, and it's IUPAC name would be 5-hydroxypentyl chloride. The "hydroxy" part is from the OH alcohol group, "pent" from the number of carbons in the chain, the "-yl chloride" is from the COCl group, which is the heaviest group, and so is the suffix. The "5" for hydroxy shows that the alcohol group is on the 5th carbon of the chain. 

The OH group is a nucleophile, so will react with the electrophilic COCl group. This is a group is a very strong electrophile, as the Cl draws the electron density away from the C=O bond, making the carbon very electron deficient. The lone pair of electrons on OH attacks the C=O bond, pushing the electrons onto the O. The O- lone pair then comes back down and kicks out the Cl, which is a very good leaving group.As there is nucleophilic attack followed by the loss of a leaving group, this mechanism is a nucleophilic addition-elimination reaction.

The new molecule is a cyclic ester, in a 6 membered ring. In an IR spectrum, the C=O group is strongly absorbing at around 1700 cm-1, so the most prominent peak would be a very sharp peak in that region due to the ester C=O. (Note: you can see that all the starting material has reacted because there would be no large absorbtion peak at around 3000cm-1 from the OH group, as this has all reacted.

DH
Answered by David H. Chemistry tutor

7443 Views

See similar Chemistry A Level tutors

Related Chemistry A Level answers

All answers ▸

why does silicon dioxide have such a high melting/boiling point?


Calculate the standard enthalpy of combustion of a methane sample by using the standard enthalpies of formation.


Explain and draw the mechanism of the nucleophillic substitution reaction between bromoethane and aqueous sodium hydroxide. How is this reaction different to the elimination reaction which may occur?


Rank the following acids according to acid strength, strongest to weakest: HF, HCl, HBr. Explain your reasoning.


We're here to help

contact us iconContact ustelephone icon+44 (0) 203 773 6020
Facebook logoInstagram logoLinkedIn logo

MyTutor is part of the IXL family of brands:

© 2025 by IXL Learning