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Get Ready for Organic Chemistry
2nd Edition
ISBN: 9780321774125
Author: KARTY, Joel
Publisher: PEARSON
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Question
Chapter 12, Problem 12.57P
Interpretation Introduction
Interpretation:
The mechanism for the given Simmons-Smith reaction is to be completed.
Concept introduction:
The Simmons-Smith reaction is an addition of CH2 across the double bond of the
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Students have asked these similar questions
In Section 12.2, we learned that the Simmons-Smith reaction produces a cyclopropane ring from an alkene.
Diiodomethane (CH,I2) is treated with a source of zinc to produce the Simmons-Smith reagent (ICH,ZnI), which reacts
with the alkene in a single elementary step. Complete the mechanism below by adding the necessary curved arrows for
this elementary step. Hint: The curved arrow notation is very similar to that for epoxidation involving a peroxyacid.)
H,
CH2
Enantiomer
+
Simmons-Smith reagent
Your answer is incorrect. Predict the relative rates of these reactions. That is, select 1 next to the reaction with the fastest rate, 2 next to the
reaction with the next fastest rate, and so on. Note for advanced students: you may assume these reactions all take place in a polar aprotic
solvent, like DMSO.
Incorrect
Your answer is incorrect.
Predict the relative rates of these reactions. That is, select I next to the reaction with the fastest rate, 2 next to the reaction with the next fastest rate, and so
on.
Note for advanced students: you may assume these reactions all take place in a polar aprotic solvent, like DMSO.
Reaction
Relative Rate
G
+ H₂O
-
OH₂
2
Br
+ H₂S
-
+ Br
3
+ H₂S
SHI
+ ci
I (fastest)
Br
+ H₂O
OM₂
+ Br
4 (slowest)
ow the mechanism for the following reaction conducted at -5 °C in CC14:
cyclohexene + bromine yields a dibromocyclohexane
Draw structures - including charges and electrons - and add curved arrows. Details count.
Step 1
Add three curved arrows to the first step.
Draw the step 1 products:
1 organic species;
1 inorganic species.
Step 2
• Reproduce the step 1 products.
Add two curved arrows to show the bromide
ion reacting with the organic species.
Draw the final product.
1L
o
↑
Map
Chapter 12 Solutions
Get Ready for Organic Chemistry
Ch. 12 - Prob. 12.1PCh. 12 - Prob. 12.2PCh. 12 - Prob. 12.3PCh. 12 - Prob. 12.4PCh. 12 - Prob. 12.5PCh. 12 - Prob. 12.6PCh. 12 - Prob. 12.7PCh. 12 - Prob. 12.8PCh. 12 - Prob. 12.9PCh. 12 - Prob. 12.10P
Ch. 12 - Prob. 12.11PCh. 12 - Prob. 12.12PCh. 12 - Prob. 12.13PCh. 12 - Prob. 12.14PCh. 12 - Prob. 12.15PCh. 12 - Prob. 12.16PCh. 12 - Prob. 12.17PCh. 12 - Prob. 12.18PCh. 12 - Prob. 12.19PCh. 12 - Prob. 12.20PCh. 12 - Prob. 12.21PCh. 12 - Prob. 12.22PCh. 12 - Prob. 12.23PCh. 12 - Prob. 12.24PCh. 12 - Prob. 12.25PCh. 12 - Prob. 12.26PCh. 12 - Prob. 12.27PCh. 12 - Prob. 12.28PCh. 12 - Prob. 12.29PCh. 12 - Prob. 12.30PCh. 12 - Prob. 12.31PCh. 12 - Prob. 12.32PCh. 12 - Prob. 12.33PCh. 12 - Prob. 12.34PCh. 12 - Prob. 12.35PCh. 12 - Prob. 12.36PCh. 12 - Prob. 12.37PCh. 12 - Prob. 12.38PCh. 12 - Prob. 12.39PCh. 12 - Prob. 12.40PCh. 12 - Prob. 12.41PCh. 12 - Prob. 12.42PCh. 12 - Prob. 12.43PCh. 12 - Prob. 12.44PCh. 12 - Prob. 12.45PCh. 12 - Prob. 12.46PCh. 12 - Prob. 12.47PCh. 12 - Prob. 12.48PCh. 12 - Prob. 12.49PCh. 12 - Prob. 12.50PCh. 12 - Prob. 12.51PCh. 12 - Prob. 12.52PCh. 12 - Prob. 12.53PCh. 12 - Prob. 12.54PCh. 12 - Prob. 12.55PCh. 12 - Prob. 12.56PCh. 12 - Prob. 12.57PCh. 12 - Prob. 12.58PCh. 12 - Prob. 12.59PCh. 12 - Prob. 12.60PCh. 12 - Prob. 12.61PCh. 12 - Prob. 12.62PCh. 12 - Prob. 12.63PCh. 12 - Prob. 12.64PCh. 12 - Prob. 12.1YTCh. 12 - Prob. 12.2YTCh. 12 - Prob. 12.3YTCh. 12 - Prob. 12.4YTCh. 12 - Prob. 12.5YTCh. 12 - Prob. 12.6YTCh. 12 - Prob. 12.7YTCh. 12 - Prob. 12.8YTCh. 12 - Prob. 12.9YTCh. 12 - Prob. 12.10YTCh. 12 - Prob. 12.11YTCh. 12 - Prob. 12.12YT
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