Concept explainers
(a)
Interpretation:
The mechanism with appropriate arrows showing the conversion of intermediate A to B through two
Concept introduction:
Carbocation intermediate can rearrange to become more stable via two possible rearrangements,
(b)
Interpretation:
The mechanism with appropriate curved arrows showing the conversion of intermediate B to Lanosterol is to be drawn.
Concept introduction:
The Carbocation intermediate rearrangement is followed by electrophilic elimination resulting in the formation of C=C bond.
Two curved arrows are needed to show electrophilic elimination. The first curved arrow originates from the base to the electrophile, and the second arrow is drawn from the electrophile to the mid of the C-C bond where C=C bond is formed.
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Organic Chemistry: Principles and Mechanisms (Second Edition)
- Identify A–E.arrow_forwardDraw the reaction mechanism using curved arrows. What mechanism is involved? From what can it be deduced?arrow_forwardDraw a mechanism for the reaction of the ketone with hydronium ion. In the first box, draw any necessary curved arrows. Show the products of the reaction in the second box. Include any nonzero formal charges and all lone pairs of electrons.arrow_forward
- Identify A through H.arrow_forwardH8. For the addition of bromine to fumaric acid, which stereoisomer(s) is/are formed in this reaction? Draw a mechanism that explains the stereochemical outcome.arrow_forwardDraw a mechanism to show how the cyanide anion (-CN) reacts with butan-2-one, and afurther mechanism to show how this initial product would react with dilute acid (+H).arrow_forward
- Retrosynthesis. Correctly complete the following: a. Predict a synthetic pathway to achieve the following product. ⟶arrow_forwardWhen 1-methoxy-2-methylpropene is treated with HCl, the major product is 1-chloro-1-methoxy-2-methylpropane. Although this reaction proceeds via an iconic mechanism, the Cl is ultimately positioned at the less substituted carbon. Draw a mechanism with this outcome and explain why the less substituted carbonation intermediate is more stable. Explanation: The less substituted carbonation has better stabilization because of a. resonance b. electron donation by the methyl groups c. reduced steric hindrance d. electron withdrawal by the methyl groups while the more substituted carbon is only stabilized by: a. resonance b. electron donation by the methyl groups c. reduced steric hindrance d. electron withdrawal by the methyl groupsarrow_forwardHow does an SN1 reaction mechanism form answers A and C?arrow_forward
- EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT