Interpretation: Among the given two molecules, the major product that is formed by
Concept Introduction:
Addition reaction of dienes:
The diene with a four carbon system is
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Chapter 20 Solutions
Organic Chemistry
- 1,3-pentadiene reacts with HBr. When the double bond at the 3-position reacts, the hydrogen attaches to the 4-carbon, thus forming an allylic carbocation with delocalized electrons. This carbocation has another resonance structure. Because there are equal amounts of diene and hydrogen bromide, in which molecule only one of the double bonds reacts. Which of the following correctly describes this new resonance structure? a) It has a double bond between carbons 3 and 4 b) It has a positive charge on carbon 2 c) It has a positive charge on carbon 4 d) It has a double bond between carbons 2 and 3arrow_forwardNAME and DRAW the STRUCTURE of ALL the alkenes which could undergo catalytic hydrogenation at 900°C to form methylcyclopentane. Circle the alkene with the HIGHEST stability and X the alkene with the HIGHEST heat of hydrogenation. Give reasons for your choice.arrow_forwardWhat would be the major product obtained from the reaction of Br2 with 1-butene if the reaction were carried out in the solvent dichloromethane? Draw the molecule.arrow_forward
- Two substitution products result from the reaction between 3-chloro-3-methyl-1- butene with sodium acetate (CH3COO – Na +) in acetic acid under SN1. Identify the products.arrow_forwardDraw the organic product that is expected to form when the following compound is oxidized under biological conditions. oxidation SH reduction • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. • If no reaction occurs, draw the organic starting material.arrow_forward(dehydrobromination) A chemist carried out an elimination reaction of 1,1-dimethyl-2- bromocyclopentane. The chemist expected the reaction to yield alkene Z as product. However, alkene Z DID NOT form. Instead, three alkenes were produced: one alkene was the major product, the other two alkenes was the minor products. What was the major alkene product that formed? Br Select one: A. I B. II C. IV D. III alcohol HEAT || Z = + (HBr) IVarrow_forward
- Draw the mechanism of the hydroboration reaction for 1-octene. Why are carbocation rearrangements not observed in this reaction?arrow_forwardWhen 2-bromobutane is reacted with CH3O-, two alkene products, namely 2-butene and 1-butene are obtained. Explain why the E2 reaction produces 2-butene as the major product (80%) and 1-butene as the minor product (20%)arrow_forwardAlkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions -X티 Hö: H-O -CH3 -CH3 H30*arrow_forward
- Show how to control the stereochemistry and regiochemistry (orientation) of additions to alkenes to obtain the products we want.arrow_forwardDraw the alkene that would react with the reagent given to account for the product formed. OH H₂SO4 CH3CH2CCH2CH3 ? + H₂O CH2CH3 . You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one.arrow_forwardReaction of 2-methyl-2-butene (above) with HBr might, in principle, lead to a mixture of two alkyl bromide addition products. Draw these two alkyl bromides.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningMacroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks Cole