What is the expected alkyl bromide product from reaction: 3-methyl-1-butanol with HBr

Expert Solution

When 3-methyl-1-butanol reacts with HBr, the expected alkyl bromide product formed is 2-Bromo-3-methylbutane.

The mechanism of the product follows the following four steps:

1. Protonation

2. Formation of primary carbocation by elimination of water molecule.

3. Re-arrangement by the hydride ion shift

4. Nucleophilic attack

The whole mechanism is explained in the following images:

queen_honey_blossom answered 10 months ago

Why is that when 3-methyl-2-butanol is treated with HBr, a single alkyl bromide is formed that...

Why is that when 3-methyl-2-butanol is treated with HBr, a single alkyl bromide is formed that results from a hydride shift and when 2-methyl-1-propanol is treated with HBr, no rearrangement occurs to form an alkyl bromide ??

What is the major organic product obtained from the following reaction? HBr

Hydrochloric acid and hydrobromic acid react with both 3-methyl-2-butanol and 2-methyl-2-butanol to form halides or alkenes,...

Hydrochloric acid and hydrobromic acid react with both 3-methyl-2-butanol and 2-methyl-2-butanol to form halides or alkenes, while nitric acid reacts with the aromatic ring in 1,4-dimethoxybenzene. Why does sulfuric acid allow for the formation of the desired product in high yields? 1. The alcohols used in this lab cannot undergo elimination reactions, so using sulfuric acid cannot result in any side products. 2. Acetic acid in the solution prevents the formation of side products by acting as an electrophile, enhancing...

Which alkyl bromide reacts fastest with sodium iodide in acetone:1- bromobutane or neopentyl bromide? Is this...

Which alkyl bromide reacts fastest with sodium iodide in acetone:1- bromobutane or neopentyl bromide? Is this consistent with your prediction? If not, what were you expecting? Explain the difference inreactivity even though both of these are primary alkyl bromides. Which solvent gave the fastest reaction; acetone or the ethanol/acetone mixture? Is this consistent with your prediction? If not, what were you expecting? Explain how the solvent affects the rate in the SN2 reaction. Explain the reactivity of bromobenzene in the...

SN2 Reactions of Alkyl Halides 1.a) Which alkyl bromide reacted fastest with sodium iodide in acetone:...

SN2 Reactions of Alkyl Halides 1.a) Which alkyl bromide reacted fastest with sodium iodide in acetone: 1-bromobutane, 2-bromobutane or 2-bromo-2-methylpropane? b) Which alkyl bromide reacted slowest? Explain how the structure of the alkyl halide affects the rate of an SN2 reaction. 2. a)Which alkyl bromide reacted faster with sodium iodide in acetone: 1-bromobutane or 1-bromo2,2-dimethylpropane (neopentyl bromide)? b)Both of these are primary halides. Why was there a difference in reactivity? 3.a)Which halide reacted faster with sodium iodide in acetone: 1-bromobutane...

1.) Methyl butyrate is made by an acid catalyzed condensation of a. Butanol and methanoic acid...

1.) Methyl butyrate is made by an acid catalyzed condensation of a. Butanol and methanoic acid b. Methyl butyric acid and methanol c. Butyric acid and sodium methoxide d. Methanol and butyric acid 2.) True or false: Esters have a lower potential for hydrogen bonding than either alcohols or carboxylic acids.

Hydrogen bromide, HBr, is a colourless gas. Consider its dissociation reaction 2HBr (g) « H2 (g)...

Hydrogen bromide, HBr, is a colourless gas. Consider its dissociation reaction 2HBr (g) « H2 (g) + Br2 (g) DfHo (kJ/mol) -36.4 +30.9 So (J/K.mol) +198.7 +130.7 +245.5 ooo a) Determine DeltaH , DeltaS , DeltaG , and Kp (all at T= 298 K) for this reaction. b) A 100. mL constant volume reaction vessel is loaded with 0.05 mol HBr and heated to 800 K. Calculate the equilibrium constant for this temperature and the partial pressure of Br2 in...

Vitride has the formula NaAlH2(OCH2CH2OCH3)2. it can be added to alkyl bromide / magnesium solutions to start a gringnard reaction.

Vitride has the formula NaAlH2(OCH2CH2OCH3)2. it can be added to alkyl bromide / magnesium solutions to start a gringnard reaction. however it is a hydride source and is capable of adding to the c=o bonds in addition to reacting with water. these questions pertain to an organic lab I did. we prepared an gringnard reaction of 0.05g (0.021 moles) Mg with 2.5mL (0.023 mol) of 1-bromobutane and 1.8mL(0.0197 moles) of 2-methylpropanal as the electrophilie. 1) As a preventative measure,...

The dehydration of 2-methyl-2-butanol in sulfuric acid produces 2 elimination products. However, this same reaction can...

The dehydration of 2-methyl-2-butanol in sulfuric acid produces 2 elimination products. However, this same reaction can also undergo substitution. What is the product of the substitution reaction?

1) What alkene(s) will be produced when each of the following alcohols is dehydrated? Cyclopentanol 2-methyl-2-butanol...

1) What alkene(s) will be produced when each of the following alcohols is dehydrated? Cyclopentanol 2-methyl-2-butanol 2) What is the purpose of adding 2% sodium carbonate solution to the distillate in Experiment A? 3) If 8.0 grams of cyclohexanol are used in Experiment A, add 5.5 grams of cyclohexene are produced, what is the percentage yield? 4) The dehydration of 3,3-dimethyl-2-butanol yields three different products. Write equations to show how carbocation rearrangements explain two of the products. 5) List four...

Question