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Organic Chemistry: A Guided Inquiry

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter8: Addition Via Carbocation

Section: Chapter Questions

Problem 8E

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Question

2. Draw the missing structure(s) in each of the following reactions. The missing
structure(s) can be a starting material or the major reaction product(s). Structures
you draw should take into account the regiochemistry and stereochemistry of
electrophilic additions to alkenes. If a starting material + reagent will not react,
write "No Rxn" in the product box. If a product can't be prepared from the reagent
specified and any alkene, write "Not possible" in the reactant box.
C5H10
H-CI
CH2Cl2
-0

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Curved arrows are used to illustrate the flow of electrons. Follow the arrows and draw the starting material and product in this reaction. Include all lone pairs and charges as appropriate. Ignore stereochemistry. Ignore inorganic byproducts.
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i. Fill in the missing starting materials, products, or reagents as necessary. ii. Label each transformation as SN1, SN2, or acid/base. iii. Indicate if the product is racemic or a single enantiomer
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Do hydration reactions like this one have Markovnikov and anti-Markovnikov products? I know that for addition of halides on alkene double bonds, there are Markovnikov products becasue of 1,2-halide/methyl shifts, but there usually aren't shifts in hydration reactions. Essentially, would the Markovnikov/major product for this reaction have a hydroxy group attached to the tertiary carbocation and the anti-Markovnikov/minor product for this reaction have a hydroxy group attached to the adjacent secondary carbocation?
Once treated with HBr, which alkene is the most likely to undergo a carbocation rearrangement after the electrophilic addition step?
Curved arrows are used to illustrate the flow of electrons. Follow the arrows and draw the intermediate and product in this reaction. Include all lone pairs and charges as appropriate. Ignore stereochemistry. Ignore inorganic byproducts.

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