What is the reaction product between Bromotoluene and sodium amide?

Question: Reaction of ortho-bromotoluene with sodium amide in liquid ammonia produces two major products, ortho-toluidine (i.e., 2-methylaniline) and mete-toluidine (i.e., 3-methylaniline).

What does sodium amide do?

Uses. Sodium amide is mainly used as a strong base in organic chemistry, often in liquid ammonia solution. It is the reagent of choice for the drying of ammonia (liquid or gaseous). One of the main advantages to the use of sodium amide is that it mainly functions as a nucleophile.

What does NaNH2 in liq NH3 do?

NaNH2 in Liq NH3 acts as a strong base. It is used in the following reactions: (1) Reaction involving alkynes to abstract acidic hydrogen. (2) To form alkyne from vicinal halide.

What happens when chlorobenzene is treated with Sodamide in the presence of liquid ammonia?

Chlorobenzene reacted with the very strong base sodium amide NaNH2 at low temperature −33oC in liquid ammonia to give aniline (aminobenzene).

Is sodium amide a strong base?

Sodium amide is a strong base. For example, it can be used as shown here to deprotonate a terminal alkyne such as propyne to produce an alkyne anion.

Is NaNH2 stronger than NaOH?

When a strong acid is dissolved in water, it reacts with it to form hydronium ion (H3O+). Thus, even though sodium amide (NaNH2) is an exceptional base (pKa of NH3 ~ 33), in water it is only as good as sodium hydroxide. On the other hand, NaNH2 is a far more basic reagent in ammonia than is NaOH.

How do you handle sodium amide?

Handling. Wear safety glasses, impervious gloves and a fire-retardant laboratory coat. Control ignition sources and avoid dust formation. Avoid contact with water or moisture.

What is amide formula?

6.9 Amides The simplest amides are derivatives of ammonia (NH3) in which one hydrogen atom has been replaced by an acyl group. Closely related and even more numerous are amides derived from primary amines (R′NH2) with the formula RC(O)NHR′.

Is NaNH2 acid or base?

NaNH2 is a strong base, intended to be strong enough to deprotonate the alkyne (pKa ≈ 25). But that would also make it strong enough to deprotonate the alcohol (pKa ≈ 16, close to water), and because the alcohol is a stronger acid, it would be deprotonated first.

When chlorobenzene is treated with soda mine and liquid nh3 the product is?

When chlorobenzene is treated with NaNH2in liquid ammonia at 196K, aniline is formed.

What is the formula of Sodamide?

NaNH2
Sodium amide/Formula

Is NaOH or NaNH2 a stronger base?

NaNH2 has a stronger conjugate acid than that of NaOH, so NaNH2 is a stronger base than NaOH NaOH is a stronger base but nitrogen is more polarizable NaNH2 has a weaker conjugate acid than that of NaOH, so NaNH2 is a stronger base than NaOH OH-is a stronger base.

How does the reaction of ortho-bromoanisole and potassium amide work?

The reaction of ortho -bromoanisole with potassium amide in liquid ammonia (b. p. -33 °C) is extremely rapid. Step 1. The amide ion attacks the H atom that is ortho to C3, generating a carbanion. Step 2. Loss of Br- to form a benzyne intermediate. The elimination is by an E2cb pathway.

How is bromotoluene used as a solvent in the environment?

Bromotoluene may be released to the environment in waste streams and as emissions during its use as a solvent (for fats, waxes or resins, and as a medium for carrying out reactions) and as chemical intermediate(1,2). Use of 2-bromotoluene as a solvent may result in direct environmental release through evaporation.

What kind of liquid is m-bromotoluene?

M-bromotoluene is a clear colorless liquid. (NTP, 1992) National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina. Budavari, S. (ed.).

What is the SRC of 2 bromotoluene?

Using an estimation method based on molecular connectivity indices(1), the Koc for 2-bromotoluene is estimated to be 440(SRC). According to a suggested classification scheme(2), this Koc value suggests that 2-bromotoluene will have medium mobility in soil(SRC).