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Interpretation:
The stereoisomers formed in the reaction of acid catalysed dehydration of 3,4-dimethyl-3-hexanol and the major product has to be determined.
Concept Introduction:
Dehydration reaction:
Removal of water molecule from the reaction when the alcohol is treated with strong acid like sulfuric acid is known as dehydration reaction, for example
Alcohols are reacts with acids like hydrochloric acid or hydrobromic acid to yield the corresponding carbocation intermediates and then the carbocation intermediate undergoes elimination reaction to give a corresponding
The stability of carbocation is given below,
Tertiary carbocation is more stable than the secondary and primary.
Cis–trans isomerism (or) geometric isomerism or configurational isomerism:
- If the
functional groups are in the same side of the carbon chain, then it is called cis isomer. - If the functional groups are in opposite to each other in the carbon chain, then it is called Trans isomer.
- If two similar functional groups are in same side which is called as Z-isomer.
- If two similar functional groups are opposite side which is called as E-isomer.
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Chapter 9 Solutions
Pearson eText for Essential Organic Chemistry -- Instant Access (Pearson+)
- Which of the compound(s) is expected to be the major product in the acid-catalyzed elimination of 2-Methylcyclohexanol? O 4-Methylcyclohexene O 1-Methylcyclohexene O 3-Methylcyclohexene O 2-Methylcyclohexene O Methylenecyclohexanearrow_forwardAcid-catalyzed dehydration of 3-methyl-2-pentanol gives three alkenes: 3-methyl-1-pentene, 3-methyl-2-pentene, and 3-methylenepentane. Draw the structure of the carbocation intermediate leading to the formation of 3-methyl-2-pentene.arrow_forwardWhich is an alkylation product of benzene? NO2 CH3 NH2 В А A Вarrow_forward
- If 1-bromopentane is heated in acetone containing NaOH, what is the alkane produced? Draw and explain the step-by-step mechanism of the production of the compoundarrow_forwardThe southern pine beetle utilizes a multi-component aggregation pheromone (one component shown below) to start mass colonization of healthy trees. The biosynthetic pathway involves the cyclization of this acetal from the straight chain structure. Draw the straight chain structure that could be used to form this acetal. Use wedges and dashes to correctly depict the stereochemistry. HgC O OH aarrow_forwardWhen the following compound is treated with a mixture of nitric and sulfuric acids, which of the following will be produced? O 5-chloro-2-nitrotoluene O 3-chloro-2-nitrotoluene O a mixture of 5-chloro-2-nitrotoluene. 3-chloro-4-nitrotoluene, 3-chloro-2-nitrotoluene, and 5-chloro-3-nitrotoluene O an equimolar mixture of 3-chloro-2-nitrotoluene. 5-chloro-2-nitrotoluene, and 3-chloro-4-nitrotoluene O 5-chloro-3-nitrotoluene O a mixture of 3-chloro-4-nitrotoluene (major) and 5-chloro-2-nitrotoluene (minor) O3-chloro-4-nitrotoluenearrow_forward
- If the reaction of an alcohol with PB13 follows an SN2 mechanism, what is the stereochemistry of the alkyl bromide formed from (2R)-2-butanol?arrow_forwardHow many stereoisomers are obtained from the reaction of 3-methyl-2-butanone with each of the following organometallic reagents followed by the addition of dilute acid? Name each stereoisomer. ethyllithium methylmagnesium bromidearrow_forwardThe major product from the dehydration of 2-methylcyclohexanol with H2SO4 catalyst is O 2-Methylcyclohexene O 1-Methylcyclohexene O 5-Methylcyclohexene O 4-Methylcyclohexene O 3-Methylcyclohexenearrow_forward
- Draw the two reactants used to form the following compound, label the nucleophile and the electrophile, and using arrows show the points of attack of the nucleophile on the electrophile that enables the formation of the heterocyclic product.arrow_forwardWhich of the following sequences of reactions would convert toluene to 2-bromo-4-cyanotoluene? ? Br CN Nitration, bromination, reduction, diazotization, reaction with cyanide anion Bromination, nitration, reduction, diazotization, reaction with cyanide anion Bromination, nitration, diazotization, reduction , reaction with cyanide anion Nitration, bromination, diazotization, reduction, reaction with cyanide anionarrow_forwardexplain why cis-2-chloro-1-cyclohexanol yields a cyclohexanone but the trans isomer yields cyclohexene oxidearrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningEBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
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