Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 6, Problem 43DSP
Interpretation Introduction
Interpretation:
The reaction which takes place at the fastest rate is to be determined.
Concept Introduction:
In general,
Primary alkyl halides are less crowded at the site of substitution than secondary and tertiary alkyl halides, and thus, react faster in substitution by
Among the alkyl halides, alkyl iodides undergo nucleophilic substitution at the fastest rate while alkyl fluorides at the slowest rate.
The strength of nucleophilicity increases from top to bottom in a group.
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b) Fill in the gaps by drawing the structures of the missing reagents, intermediates and/or
products of the following electrophilic aromatic substitutions. Chemical formulas have been
added for guidance.
Step 1
Step 2
CH3
HNO3
H2
1.
C6H5NO2
C,HgN
H2SO4
`NO2
Pd/C
1
2
4
CH3
Br2/FeBr3
C3H;Bro
5
6
Using resonance structures, justify whether the acetyl group of compound 5 will direct the
bromination reaction to the meta or ortho/para positions.
Answer the following questions regarding the nucleophilic substitution reaction shown below:
CH3CH2CH2-Br + I- ------> CH3CH2CH2I + Br-
(a) Write the rate law for this reaction assuming that it is a one step reaction that is first order in each of the reactants.
(b) Holding the concentration of the iodide ion constant, what change would be observed in the rate if the concentration of the n- propyl bromide was tripled?
(b) Assume that this is an exothermic reaction, draw the energy profile and identify the location of the transition state.
(c) Draw the transition state for this reaction.
(d) What change is observed for the entropy of the system during this reaction?
(e) Show the likely mechanism of this reaction using the proper curved arrows
Imagine that phenol (“hydroxybenzene”) and nitrobenzene are reacted (in separate beakers) with a hot solution containing both concentrated sulfuric acid and concentrated nitric acid.
A) In analyzing the products, you discover that the substitution pattern resulting from the reaction with phenol differs from the reaction with nitrobenzene. Explain this difference in substitution patterns using one or more judiciously selected reaction mechanisms or portions of mechanisms.
Chapter 6 Solutions
Organic Chemistry - Standalone book
Ch. 6.1 - Prob. 1PCh. 6.2 - 1-Bromo-3-chloropropane reacts with one molar...Ch. 6.3 - Prob. 3PCh. 6.3 - The Fischer projection for (+)-2-bromooctane is...Ch. 6.3 - Would you expect the 2-octanol formed by SN2...Ch. 6.3 - Prob. 6PCh. 6.4 - Prob. 7PCh. 6.4 - The first step in the synthesis of the...Ch. 6.6 - Prob. 9PCh. 6.6 - Prob. 10P
Ch. 6.7 - Prob. 11PCh. 6.8 - Prob. 12PCh. 6.9 - Diethyl ether (CH3CH2OCH2CH3) has a dielectric...Ch. 6.9 - Unlike protic solvent which solvate from complexes...Ch. 6.10 - Prob. 15PCh. 6.10 - Prob. 16PCh. 6.10 - The hydrolysis of sulfonate of 2-octanol is...Ch. 6.11 - Prob. 18PCh. 6 - Prob. 19PCh. 6 - Prob. 20PCh. 6 - Both of the following reactions involve...Ch. 6 - Prob. 22PCh. 6 - Prob. 23PCh. 6 - Sodium nitrite (NaNO2) reacted with 2-iodooctane...Ch. 6 - Prob. 25PCh. 6 - Prob. 26PCh. 6 - Prob. 27PCh. 6 - The reaction of 2,2-dimethyl-1-propanol with HBr...Ch. 6 - If the temperature is not kept below 25oC during...Ch. 6 - The reaction of cyclopentyl bromide with sodium...Ch. 6 - Prob. 31PCh. 6 - Prob. 32PCh. 6 - Write an equation, clearly showing the...Ch. 6 - Prob. 34PCh. 6 - Based on what we know about nucleophiles and...Ch. 6 - Prob. 36PCh. 6 - Prob. 37PCh. 6 - Prob. 38PCh. 6 - Prob. 39PCh. 6 - Prob. 40PCh. 6 - Prob. 41DSPCh. 6 - Prob. 42DSPCh. 6 - Prob. 43DSPCh. 6 - Prob. 44DSPCh. 6 - Prob. 45DSPCh. 6 - Prob. 46DSP
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