Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 8, Problem 35P
Interpretation Introduction
(a)
Interpretation: The by-products of the given reaction are to be drawn and the movement of electrons is to be shown by using curved arrow notation.
Concept introduction: In E2 elimination reactions, the proton is abstracted from the beta carbon to form an
Interpretation Introduction
(b)
Interpretation: The effect of the given change on the reaction rate is to be stated.
Concept introduction: In E2 elimination reactions, substituents which are adjacent to each other are eliminated from an alkyl halide to form an alkene. A concerted mechanism is followed for this type of reactions.
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Draw the energy diagram of the following reaction (label and draw reactants, intermediates, and products). Label transition state of the rate limiting step and draw the transition state of the rate determining step. Is it a concerted or stepwise reaction? Write the rate law for this reaction. How do we increase the reaction rate? If we use deutrium-tert-butyl bromide such as (CD3)3CBr instead of (CH3)3CBr, will it increase or decrease the reaction rate? Or there is no meaningful rate change. Write reasons for your answer. Draw mechanisms for reactions by drawing arrows and intermediates.
Br
CH2
HBr
CH3
Draw curved arrows to show the movement of electrons in this step of the reaction mechanism.
Arrow-pushing Instructions
CH2
Н— Br:
The mechanism proceeds through a first cationic intermediate, intermediate 1. Nucleophilic attack leads to intermediate 2, which goes on to form the final product. In cases that involve
negatively charged nucleophile, the attack of the nucleophile leads directly to the product.
H.
Br
+ CH3OH
Br
Intermediate 2
(product)
Intermediate 1
In a similar fashion, draw intermediate 1 and intermediate 2 (final product) for the following reaction.
OCH3
Cl2
MEOH
ĆI
racemic mixture
Pay attention to the reactants, they may differ from the examples. In some reactions, one part of the molecule acts as the nucleophile.
• You do not have to consider stereochemistry.
• Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate intermediate 1 and intermediate 2 using the
the dropdown menu.
→ symbol from
Chapter 8 Solutions
Organic Chemistry (6th Edition)
Ch. 8.1 - Problem 8.1 Label the and carbons in each alkyl...Ch. 8.2 - Problem 8.2 Classify each alkene in the following...Ch. 8.2 - Prob. 3PCh. 8.2 - Prob. 4PCh. 8.2 - Problem 8.5 Label each pair of alkenes as...Ch. 8.2 - Problem 8.6 Which alkene in each pair is more...Ch. 8.2 - Problem 8.7 Several factors can affect alkene...Ch. 8.4 - Prob. 8PCh. 8.4 - Prob. 9PCh. 8.4 - Prob. 10P
Ch. 8.4 - Prob. 11PCh. 8.5 - Problem 8.12 What alkenes are formed from each...Ch. 8.6 - Prob. 13PCh. 8.6 - Problem 8.14 What alkenes are formed from each...Ch. 8.6 - Problem 8.15 How does each of the following...Ch. 8 - 8.24 Rank the alkenes shown in the ball-and-stick...Ch. 8 - Prob. 25PCh. 8 - 8.26 What is the major E2 elimination product...Ch. 8 - Prob. 27PCh. 8 - Prob. 28PCh. 8 - Prob. 29PCh. 8 - 8.30 Label each pair of alkenes as constitutional...Ch. 8 - Prob. 31PCh. 8 - Prob. 32PCh. 8 - Prob. 33PCh. 8 - For each of the following alkenes, draw the...Ch. 8 - Prob. 35PCh. 8 - Prob. 36PCh. 8 - Prob. 37PCh. 8 - What alkene is the major product formed from each...Ch. 8 - Prob. 39PCh. 8 - Prob. 41PCh. 8 - Draw the products formed when each dihalide is...Ch. 8 - Draw all of the substitution and elimination...Ch. 8 - Prob. 56PCh. 8 - 8.59 Draw a stepwise, detailed mechanism for each...Ch. 8 - Draw the major product formed when...Ch. 8 - Draw a stepwise, detailed mechanism for the...Ch. 8 - Explain why the reaction of with gives ...Ch. 8 - Draw a stepwise detailed mechanism that...Ch. 8 - Prob. 63PCh. 8 - 8.65 Explain the selectivity observed in the...Ch. 8 - Prob. 65PCh. 8 - Prob. 66PCh. 8 - 8.68 (a) Draw all products formed by treatment of...
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