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Chapter 20: Q13P (page 1038)

The reaction of tert-butyl alcohol with concentrated HCl goes by the SN1 mechanism. Write a mechanism for this reaction.

Short Answer

Expert verified

In a Unimolecular nucleophile substitution ( SN1 ) reaction, only one molecule (carbocation formation) is involved in the 鈥渞ate-determining step.鈥�

Unimolecular nucleophilic substitution is also known as a first-order reaction.

Hydrolysis of tertiary alkyl halide follows a Unimolecular nucleophilic substitution reaction.

Step by step solution

01

Unimolecular Nucleophilic substitution Reaction ( SN1 )

In a Unimolecular nucleophile substitution ( SN1 ) reaction, only one molecule (carbocation formation) is involved in the 鈥渞ate-determining step.鈥�

Unimolecular nucleophilic substitution is also known as a first-order reaction.

Hydrolysis of tertiary alkyl halide follows a Unimolecular nucleophilic substitution reaction.

02

Formation of 1- bromo-1-methylcyclohexane from tert-butyl alcohol

tert-butyl alcoholis tertiary alcohol; thus, it will react with HCl by the SN1 mechanism.

Protonation of tert-butyl alcoholconverts the hydroxy group to a good leaving group.

Water leaves, forming a carbocation.

Bromide ion attacks the carbocation to form the product 2-chloro-2-methylpropane.

Mechamism of forming 2-chloro-2-methylpropane

Mechanism of formation of 1- bromo-1-methylcyclohexane

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Most popular questions from this chapter

Question: Give both IUPAC names and common names for the following compounds.

(a) phCH2COOH

(b) phCO2Na

(c) (CH3)2 CHCHCICOOH

(d) HOOC (CH2)4CO2H

(e) (CH3)2 CHCH2COOK

(f) CH3 CH(NH2) COOH

(g)

(h)

(i)

Which of the following compounds are chiral? Draw each compound in its most symmetric conformation, star any asymmetric carbon atoms, and draw any mirror planes. Label any meso compounds. You may use Fischer projections if you prefer.

(a) meso-2,3-dibromo-2,3-dichlorobutane

(b) -2,3-dibromo-2,3-dichlorobutane

(c) (2R,3S)-2-bromo-3-chlorobutane

(d) (2R,3S)-2,3-dibromobutane

(e) (R,R)-2,3-dibromobutane

(f)

(g)

(h)

Circle the isoprene units in geranial, menthol, camphor, and abietic acid.

Question: Show how you would synthesize the following carboxylic acids, using the indicated starting materials.

(a) hex-3-yne鈫�propanoicacid

(b) cis-cyclodecene鈫�decanedioicacid

(c ) iodobenzene鈫�phenylaceticacid

(d)pentan-3-ol鈫�2-ethylbutanoicacid

(e)o-xylene鈫�phthalicacid

(f) allylbromide鈫�but-3-enoicacid

Question:

  1. Determine the structure of the carboxylic acid whose proton NMR spectrum appears below.
  2. Draw the NMR spectrum you would expect from the corresponding aldehyde whose oxidation gives this carboxylic acid.
  3. Point out two distinctive differences in the spectra of the aldehyde and the acid.
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