Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 7, Problem 53P
Interpretation Introduction
Interpretation:
Theelementary steps depicting the mechanisms of each of the given reaction are to be written.
Concept introduction:
>The dehydration of secondary and tertiary alcohol proceeds through
The
Thestability order of carbocation is methyl
The carbocation may be rearrangedbyshift of hydride oralkyl group of adjacent carbons.
>The selection of hydride or alkyl group shift depends on the stability of the carbocation formed.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Although benzene is normally written with three double bonds, benzene is not reactive towards many reagents that alkenes normally react with. This lack of reactivity can be explained by the unusual stability created by cyclic conjugation. First, (i) describe at least one of the physical properties of benzene that demonstrates how the true structure of benzene does match the way the structure is normally written. Then, (ii) explain how the unusual stability of benzene can be demonstrated by its thermodynamic properties through some form of experiment. Be sure to (iii) include an appropriately labeled diagram as part of your answer (you do not have to quote any numerical values).
G. (a) Identify the acid and base in each of the following reaction. (b) Show the
mechanism by using arrows. (c) For each reaction, what acid-base concept (or
definition) is applicable in classifying them? Explain why.
Label the acid and base below the structure.
Acid-base concept.
Explanation
Draw arrow (You may copy/paste the reaction in
paint or powerpoint to be able to draw the arrow. You
may also draw the arrow manually.)
1. :0:
II
CHIC-H + CH30:
:ö:
CH3C-H
:OCH3
H
2.
:0:
:0:
+
H
CH3-C-CH3 +
CH3-C-CH3
H-
1) Complete the following reaction and provide a detailed, step-by-step mechanism for
the process.
HBr
Chapter 7 Solutions
Organic Chemistry - Standalone book
Ch. 7.1 - Name each of the following using IUPAC...Ch. 7.1 - Prob. 2PCh. 7.2 - How many carbon atoms are sp2-hybridized in the...Ch. 7.3 - Prob. 4PCh. 7.3 - Are cis-2-hexene and trans-3-hexene stereoisomers?...Ch. 7.4 - Prob. 6PCh. 7.4 - Prob. 7PCh. 7.4 - Give the IUPAC name of each of the compounds in...Ch. 7.5 - Arrange the following in order of increasing...Ch. 7.6 - Prob. 10P
Ch. 7.6 - Standard enthalpies of formation are known for all...Ch. 7.6 - Prob. 12PCh. 7.6 - Despite numerous attempts, the alkene...Ch. 7.6 - Write structural formulas for the six isomeric...Ch. 7.7 - Place a double bond in the carbon skeleton shown...Ch. 7.9 - Identify the alkene obtained on dehydration of...Ch. 7.10 - Prob. 17PCh. 7.11 - Prob. 18PCh. 7.12 - Prob. 19PCh. 7.13 - The alkene mixture obtained on dehydration of...Ch. 7.14 - Write the structures of all the alkenes that can...Ch. 7.14 - Write structural formulas for all the alkenes that...Ch. 7.15 - A study of the hydrolysis behavior of...Ch. 7.15 - Use curved arrows to illustrate the electron flow...Ch. 7.15 - Predict the major product of the reaction shown.Ch. 7.16 - Prob. 26PCh. 7.17 - Prob. 27PCh. 7.18 - Prob. 28PCh. 7.19 - Predict the major organic product of each of the...Ch. 7.19 - A standard method for the synthesis of ethers is...Ch. 7 - Write structural formulas for each of the...Ch. 7 - Prob. 32PCh. 7 - Give an IUPAC name for each of the following...Ch. 7 - A hydrocarbon isolated from fish oil and from...Ch. 7 - Prob. 35PCh. 7 - Prob. 36PCh. 7 - Prob. 37PCh. 7 - Prob. 38PCh. 7 - Choose the more stable alkene in each of the...Ch. 7 - Suggest an explanation for the fact that...Ch. 7 - Prob. 41PCh. 7 - Write structural formulas for all the alkene...Ch. 7 - Prob. 43PCh. 7 - Prob. 44PCh. 7 - Predict the major organic product of each of the...Ch. 7 - Prob. 46PCh. 7 - Prob. 47PCh. 7 - The rate of the reaction In the first order in...Ch. 7 - Prob. 49PCh. 7 - Prob. 50PCh. 7 - You have available 2,2-dimethylcyclopentanol (A)...Ch. 7 - Prob. 52PCh. 7 - Prob. 53PCh. 7 - Prob. 54PCh. 7 - Acid-catalyzed dehydration of...Ch. 7 - The ratio of elimination to substitution is...Ch. 7 - Prob. 57PCh. 7 - Prob. 58DSPCh. 7 - Prob. 59DSPCh. 7 - Prob. 60DSPCh. 7 - Prob. 61DSPCh. 7 - A Mechanistic Preview of Addition Reactions The...Ch. 7 - Prob. 63DSPCh. 7 - Prob. 64DSPCh. 7 - Prob. 65DSP
Knowledge Booster
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
- 4. Propose a sequence of steps to carry out the following conversion. ( a) b)arrow_forwardRefer to the reaction energy diagram to answer parts (a) through (e). (a) The rate-limiting step is: ______. (b) The transition state for the fastest step is: _____. (c) In the third step which intermediate structurally resembles the transition state according to the Hammond postulate? _____. (d) Which step no. is endergonic? _____. (e) The number of intermediates in the overall reaction is: _____.arrow_forwardRefer to the reaction energy diagram to answer parts (a) through (e). (a) What is the rate-limiting STEP? (Select from 1, 2, 3, or 4) (b) The TRANSITION STATE for the fastest step is: (c) In the 3rd step which INTERMEDIATE structurally resembles the transition state according to the Hammon postulate? (d) Which STEP NUMBER is endergonic? (e) The number of intermediates in the overall reaction is:arrow_forward
- 4. Describe in table format the following criteria for S,' reactions: (a) strength of nucleophile; (b) substrate (RX); (c) solvent; (d) kinetics; (e) stereochemistry; (f) possibility of rearrangements.arrow_forwardFor the reaction scheme below: (a) Suggest a reagent X that could be used to accomplish the first step. (b) Draw the curly arrow mechanism for the second step in the scheme.arrow_forward(a) Name the reactant (including E/Z configuration) and draw the structure of the major product for the following reaction. + HBr (b) Explain your answer for the product in part (a), and include the structure of the carbocation intermediate in your explanation. (c) Draw the mechanism for the reaction in part (a), showing all intermediates and electron movement with arrows.arrow_forward
- Compound A and compound B are in equilibrium. Write a stepwise mechanism from compound Ato compound B showing ALL intermediates. Use curved arrows to symbolize the flow of electrons to show how each of the intermediates and products are formed. Show all lone pairs and formal charges. Lastly, explain which compound (Aor B) will be in higher concentration.arrow_forwardUsing cyclohexane as your starting material, show how you would synthesize each of the following compounds. (Onceyou have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.)(a) bromocyclohexanearrow_forwardUsing cyclohexane as your starting material, show how you would synthesize each of the following compounds. (Onceyou have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.)(a) bromocyclohexane (b) cyclohexenearrow_forward
- Give a clear explanation handwritten answer..complete the following reactionarrow_forwardFor each of the following, write the major product(s) and then draw out each step in the mechanism using curved arrows. Show ALL lone pair electrons and formal charges. Redraw ALL molecules as to show explicitly ALL bonds being broken or formed. Identify the molecular orbital (HOMO) of the nucleophile and the molecular orbital (LUMO) of electrophile involved in the nucleophilic attack. MO diagrams are not necessary. (a). (b). -CHO 2. H₂O 1. LiAlH4 2. H₂O MgBr , etherarrow_forward(a) What reagents would be used for the conversion of alkene A into the target? (b) What reaction is involved in the conversion of alcohol B into alkene A? Suggest a reagent that might affect this transformation. (c) Give a retrosynthetic analysis showing the disconnection of B, the synthons produced that lead to the synthetic equivalents given (draw their structures).arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage Learning
ChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill Education
Principles of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill Education
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY