ORGANIC CHEMISTRY (LL)-PACKAGE
ORGANIC CHEMISTRY (LL)-PACKAGE
8th Edition
ISBN: 9781319316389
Author: VOLLHARDT
Publisher: MAC HIGHER
bartleby

Concept explainers

bartleby

Videos

Question
Book Icon
Chapter 7.9, Problem 7.21E

(a)

Interpretation Introduction

Interpretation: The structure of the major organic product that would result from the reaction of 2-bromo-2-methylbutane water in acetone along with the dominant pathway adopted should be written.

Concept introduction: Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from alkyl halides have two fates; they can be either trapped by nucleophiles to give substitution product or may deprotonate to yield a small amount of alkene. Stronger the base more is the probability of elimination over substitution over elimination. Further, if the still higher concentration is employed reaction proceeds via bimolecular elimination. On the other hand,the weak base waits until the carbocation is formed and the type of elimination with a relatively weak base is two-step elimination or E1 .

Analogous to the case that strong nucleophiles are more favored to react via SN2 pathway, the greater concentration of strong bases are more favored for single-step elimination E2 pathway. Such strong bases include hydroxide ion or alkoxide ions. The reason of predominance of E2 elimination is that strong bases have high probabilities and high rates to abstract hydrogen from carbon adjacent to the carbocation.

(b)

Interpretation Introduction

Interpretation: The structure of the major organic products that would result from the reaction of 3-chloro-3-ethylpentane with sodium methoxide in methanol along with the dominant pathway adopted should be written.

Concept introduction:Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from alkyl halides have two fates; they can be either trapped by nucleophiles to give substitution product or may deprotonate to yield a small amount of alkene. Stronger the base more is the probability of elimination over substitution over elimination. Further, if the still higher concentration is employed reaction proceeds via bimolecular elimination. On the other hand, the weak base waits until the carbocation is formed and the type of elimination with a relatively weak base is two-step elimination or E1 .

Analogous to the case that strong nucleophiles are more favored to react via SN2 pathway, the greater concentration of strong bases are more favored for single-step elimination E2 pathway. Such strong bases include hydroxide ion or alkoxide ions. The reason of predominance of E2 elimination is that strong bases have high probabilities and high rates to abstract hydrogen from carbon adjacent to the carbocation.

Blurred answer
Students have asked these similar questions
None
Dr. Mendel asked his BIOL 260 class what their height was and what their parent's heights were. He plotted that data in the graph below to determine if height was a heritable trait. A. Is height a heritable trait? If yes, what is the heritability value? (2 pts) B. If the phenotypic variation is 30, what is the variation due to additive alleles? (2 pts) Offspring Height (Inches) 75 67.5 60 52.5 y = 0.9264x + 4.8519 55 60 65 MidParent Height (Inches) 70 75 12pt v V Paragraph B IUA > AT2 v V
Experiment:  Each team will be provided with 5g of a mixture of acetanilide and salicylic acid. You will divide it into three 1.5 g portions in separate 125 mL Erlenmeyer flasks savıng some for melting point analysis. Dissolve the mixture in each flask in ~60mL of DI water by heating to boiling on a hotplate. Take the flasks off the hotplate once you have a clear solution and let them stand on the bench top for 5 mins and then allow them to cool as described below. Sample A-Let the first sample cool slowly to room temperature by letting it stand on your lab bench, with occasional stirring to promote crystallization. Sample B-Cool the second sample 1n a tap-water bath to 10-15 °C Sample C-Cool the third sample in an ice-bath to 0-2 °C Results: weight after recrystalization and melting point temp. A=0.624g,102-115° B=0.765g, 80-105° C=1.135g, 77-108 What is the percent yield of A,B, and C.
Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
  • Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305580350
    Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
    Publisher:Cengage Learning
    Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305080485
    Author:John E. McMurry
    Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning
Coenzymes and cofactors; Author: CH15 SWAYAM Prabha IIT Madras;https://www.youtube.com/watch?v=bubY2Nm7hVM;License: Standard YouTube License, CC-BY
Aromaticity and Huckel's Rule; Author: Professor Dave Explains;https://www.youtube.com/watch?v=7-BguH4_WBQ;License: Standard Youtube License