Phenol to phenyl ethanoate

https://chem.libretexts.org/@app/auth/3/login?returnto=https%3A%2F%2Fchem.libretexts.org%2FCourses%2FUniversity_of_Illinois_Springfield%2FUIS%253A_CHE_269_(Morsch_and_Andrews)%2FChapters%2FChapter_19%253A_Acidity_of_Carboxylic_Acids%2F19.09_Carboxylic_Acids%25E2%2580%2594Strong_Organic_Br%25C3%25B8nsted%25E2%2580%2593Lowry_Acids Comparing the strengths of weak acids The strengths of weak acids are measured on the pK a scale. The smaller the number on this scale, the stronger the acid is. Three of the compounds we shall be looking at, together with their pK a values are: Remember - the smaller the number the stronger the acid. Comparing the other two to ethanoic acid, you will see that phenol is very much weaker with a pK a of 10.00, and ethanol is so weak with a pK a of about 16 that it hardly counts as acidic at all! Acidity of Carboxylic Acids The pK a 's of some typical carboxylic acids are listed in the following table. When we compare these values with those of comparable alcohols, such as ethanol (pK a = 16) and 2-methyl-2-propanol (pK a = 19), it is clear that carboxylic acids are stronger acids by over ten powers of ten! Furthermore, electronegative substituents near the carboxyl group act to increase the acidity. Compound pK a Compound pK a HCO 2H 3.75 CH 3CH 2CH 2CO 2H 4.82 CH 3CO 2H 4.74 ClCH 2CH 2CH 2CO 2H 4.53 FCH 2CO 2H 2.65 CH 3CHClCH 2CO 2H 4.05 ClCH 2CO 2H 2.85 CH 3CH 2CHClCO 2H 2.89 BrCH 2CO 2H 2.90 C 6H 5CO 2H 4.20 ICH 2CO 2H 3.10 p-O 2NC 6H 4CO 2H 3.45 ...

https://chem.libretexts.org/@app/auth/3/login?returnto=https%3A%2F%2Fchem.libretexts.org%2FBookshelves%2FOrganic_Chemistry%2FMap%253A_Organic_Chemistry_(Vollhardt_and_Schore)%2F22%253A_Chemistry_of_the_Benzene_Substituents%253A_Alkylbenzenes_Phenols_and_Benzenamines%2F22.06%253A_Electrophilic_Substitution_of_Phenols The strongest activating and ortho/para-directing substituents are the amino (-NH 2) and hydroxyl (-OH) groups. Direct nitration of phenol (hydroxybenzene) by dilute nitric acid gives modest yields of nitrated phenols and considerable oxidative decomposition to tarry materials; aniline (aminobenzene) is largely destroyed. Bromination of both phenol and aniline is difficult to control, with di- and tri-bromo products forming readily. Because of their high nucleophilic reactivity, aniline and phenol undergo substitution reactions with iodine, a halogen that is normally unreactive with benzene derivatives. The mixed halogen iodine chloride (ICl) provides a more electrophilic iodine moiety, and is effective in iodinating aromatic rings having less powerful activating substituents. C 6H 5–NH 2 + I 2 + NaHCO 3 p- I–C 6H 4–NH 2 + Na I + CO 2 + H 2O By acetylating the heteroatom substituent on phenol and aniline, its activating influence can be substantially attenuated. For example, acetylation of aniline gives acetanilide (first step in the following equation), which undergoes nitration at low temperature, yielding the para-nitro product in high yield. The modifying a...

acid anhydrides and water, alcohols or phenol THE REACTION OF ACID ANHYDRIDES WITH WATER, ALCOHOLS AND PHENOL This page looks at the reactions of acid anhydrides with water, alcohols and phenols (including the manufacture of aspirin). These reactions are all considered together because their chemistry is so similar. There is also a great similarity between acid anhydrides and acyl chlorides (acid chlorides) as far as these reactions are concerned. Concentrate on these similarities as you go through this page because it should help you to remember. Similarities between the reactions Comparing the structures of water, ethanol and phenol Each substance contains an -OH group. In water, this is attached to a hydrogen atom. In an alcohol, it is attached to an alkyl group - shown in the diagrams below as "R". In phenols, it is attached to a benzene ring. Phenol (the simplest member of the family of phenols) is C 6H 5OH. Note: If you aren't sure about using this It isn't particularly important in the context of the current page. All you need to know is that at each corner of the hexagon there is a carbon atom, together with a hydrogen atom apart from where the -OH group is attached. If you choose to follow the link, use the BACK button (or the HISTORY file or GO menu) on your browser to return to this page. Comparing the reactions of acyl chlorides and acid anhydrides with these compounds Because the formula is much easier, it helps to start with the acyl chlorides. The reactions ...

Phenol makes hydrogen bonds with water. Therefore phenol should be dissolved in water. Adding more phenol into the water will make separate layers of both substances. Phenol dissolve in ether and ethanol very well. Uses of phenol • Dilute solutions of phenol is used as germicides. • As a raw material of dyes, pharmaceutical, detol, bakelight. • to manufacture herbicide Preparation of phenol Prepare phenol from benzene We cannot synthesis phenol from benzene in a single step. We have to follow several steps to prepare phenol from benzene. • Benzene is translated into the nitrobenzene by adding concentrated sulfuric acid and Concentrated nitric acid at 40 0C. • Aniline is prepared by reduction of nitrobenzene. Zinc, concentrated HCl as added to the nitrobenzene and then add excess NaOH to the given aniline salt to release aniline. • Nitrous acid ( NaNO 2(aq) and concentrated HCl (aq) ) is added into the 0C. It will produce benzene diazonium chloride. • Finally, water is added to the benzene diazonium chloride at higher temperatures than 10 0C. • Also we can add directly NaNO 2(aq) and concentrated HCl (aq) to the aniline room temperature. This will also give phenol as the product. 2 and concentrated HCl and how to prepare HNO 2 acid Reactions of phenol Phenol is ortho para activator and a weak acid. Electrons density of benzene ring in phenol is much higher than benzene. Therefore substitutions reactions of phenol occurs much easier than benzene. Phenol reactions and their c...