preview

4-Bromoacetanalide

Better Essays

The data from the results supports the product that was synthesised was 4-Bromoacetanalide, this was proved by various factors. For example, the literature range for the melting point of 4-bromoacetanalide was 166-170 whereas the average melting point recorded from the final product made was 169.2°C, which fits within the range. Melting points are also sensitive to purity which shows the product obtained was of a pure nature as the product melting point is sharp within the range. Another way in which the product can be proved to be 4-bromoacetanalide is by the IR spectrum. The spectrum shows many peaks for different functional groups, which are found in 4-bromoacetanalide. These include the peaks for the secondary amine (N-H) at 3303.1cm-1, …show more content…

The reason for the percentage yield being slightly low may be due to when substances are being transferred from different beakers and flasks, which lead to some product being lost, also when being filtered, some of the product may have been left on the filter paper or hadn't formed to crystals yet, which lead to it passing through the filter paper and into the flask. Also, not every molecule in the reaction might have reacted which lead to a loss of product. This could be improved by minimising the amount of transfer between different flasks and beakers. Also, the crystals could have been left to develop for a longer period of time before being filtered by the Buchner funnel, and by taking more time to measure out each reactant so that the measurements are exact, to increase the …show more content…

It will be the first to run out and when it does it will limit the rest of the reaction as the reaction cannot continue without it.
The reaction is an electrophilic aromatic substitution, the hydrogen atom of the aromatic ring is replaced as a consequence of an electrophilic attack on the aromatic benzene ring. (chem.ucla.edu, 2015) An electrophile attacks the pi electrons of the benzene ring from acetanilide, and this forms a resonance which stables the carbocation. The carbocation is attacked and it loses a proton.
The reason the product is para-bromoacetanilide is because of the amine substituent. This gives resonance stabilization to carbocations which are created by the addition of ortho and para. The amine provides steric hindrance when it's at the ortho position, and when acetanilide is brominated, it occurs at the para position as its more stable (most resonance stabled carbocation). This affects the regiochemistry of the reaction because the ortho and para directors direct the incoming electrophile to either position ortho or para to themselves, and para is favoured as it is more

Get Access