Organic Chemistry Plus Mastering Chemistry with Pearson eText -- Access Card Package (9th Edition) (New in Organic Chemistry)
9th Edition
ISBN: 9780321971128
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 11, Problem 11.54SP
Interpretation Introduction
Interpretation: The mechanism of formation of dihydropyran is to be stated.
Concept introduction: The acid catalysis reaction of tetrahydrofurfuryl occurs through two steps. First is protonation of alcohol, second is formation of carbocation with elimination of water molecule and third is stabilisation of carbocation by hydride shift followed by the conversion of primary carbocation into secondary carbocation.
To determine: The mechanism of the given reaction.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Add conditions above and below the arrow that turn the reactant below into the product below in a single transformation.
+ More...
If you need to write reagents above and below the arrow that have complex hydrocarbon groups in them, there is a set of standard abbreviations you can use.
More...
T
H,N
NC
Dat
Indicate the order of basicity of primary, secondary and tertiary amines.
>
Classify each of the following molecules as aromatic, antiaromatic, or nonaromatic.
Cl
Z-
N
O aromatic
O antiaromatic
O nonaromatic
O aromatic
O antiaromatic
O nonaromatic
O aromatic
○ antiaromatic
nonaromatic
Chapter 11 Solutions
Organic Chemistry Plus Mastering Chemistry with Pearson eText -- Access Card Package (9th Edition) (New in Organic Chemistry)
Ch. 11.1 - Prob. 11.1PCh. 11.2C - Prob. 11.2PCh. 11.3 - Prob. 11.3PCh. 11.3 - Prob. 11.4PCh. 11.3 - Prob. 11.5PCh. 11.3 - Suggest the most appropriate method for each of...Ch. 11.4 - A chronic alcoholic requires a much larger dose of...Ch. 11.4 - Unlike ethylene glycol, propylene glycol...Ch. 11.5 - Predict the major products of the following...Ch. 11.5 - Show how you would convert propan-1-ol to the...
Ch. 11.6 - Predict the products of the following reactions....Ch. 11.7A - Propose a mechanism for the reaction of a....Ch. 11.7B - Prob. 11.13PCh. 11.7B - Show how you would use a simple chemical test to...Ch. 11.7C - Neopentyl alcohol, (CH3)3CCH2OH, reacts with...Ch. 11.7C - Prob. 11.16PCh. 11.7C - When cis-2-methylcyclohexanol reacts with the...Ch. 11.8 - Prob. 11.18PCh. 11.9 - Prob. 11.19PCh. 11.9 - Prob. 11.20PCh. 11.9 - Prob. 11.21PCh. 11.10A - Prob. 11.22PCh. 11.10A - Some alcohols undergo rearrangement or other...Ch. 11.10B - Prob. 11.24PCh. 11.10B - Explain why the acid-catalyzed condensation is a...Ch. 11.10B - Prob. 11.26PCh. 11.10B - When the following substituted cycloheptanol...Ch. 11.11A - Prob. 11.28PCh. 11.11A - Prob. 11.29PCh. 11.11B - Predict the products formed by periodic acid...Ch. 11.12 - Prob. 11.31PCh. 11.13A - Prob. 11.32PCh. 11.14 - Prob. 11.33PCh. 11.14 - a. Show how ethanol and cyclohexanol may be used...Ch. 11.14 - Prob. 11.35PCh. 11.14 - Phenols (pKa 10) are more acidic than other...Ch. 11.14 - To practice working through the early parts of a...Ch. 11.14 - Prob. 11.38PCh. 11 - Predict the major products of the following...Ch. 11 - Show how you would convert 2-methylcyclopentanol...Ch. 11 - In each case, show how you would synthesize the...Ch. 11 - Prob. 11.42SPCh. 11 - Prob. 11.43SPCh. 11 - Prob. 11.44SPCh. 11 - Both cis- and trans-2-methylcyclohexanol undergo...Ch. 11 - Prob. 11.46SPCh. 11 - Prob. 11.47SPCh. 11 - Show how you would make each compound, beginning...Ch. 11 - Predict the major products (including...Ch. 11 - Show how you would use simple chemical tests to...Ch. 11 - The compound shown below has three different types...Ch. 11 - Prob. 11.52SPCh. 11 - Prob. 11.53SPCh. 11 - Prob. 11.54SPCh. 11 - Prob. 11.55SPCh. 11 - Show how you would synthesize the following...Ch. 11 - Show how you would synthesize the following...Ch. 11 - The following pseudo-syntheses (guaranteed not to...Ch. 11 - Two unknowns, X and Y, both having the molecular...Ch. 11 - The Williamson ether synthesis involves the...Ch. 11 - Prob. 11.61SPCh. 11 - Prob. 11.62SPCh. 11 - Alcohols combine with ketones and aldehydes to...Ch. 11 - Prob. 11.64SPCh. 11 - Prob. 11.65SPCh. 11 - Prob. 11.66SP
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
- Please help me answer this question. I don't understand how or even if this can happen in a single transformation. Please provide a detailed explanation and a drawing showing how it can happen in a single transformation. Add the necessary reagents and reaction conditions above and below the arrow in this organic reaction. If the products can't be made from the reactant with a single transformation, check the box under the drawing area instead.arrow_forward2) Draw the correct chemical structure (using line-angle drawings / "line structures") from their given IUPAC name: a. (E)-1-chloro-3,4,5-trimethylhex-2-ene b. (Z)-4,5,7-trimethyloct-4-en-2-ol C. (2E,6Z)-4-methylocta-2,6-dienearrow_forwardපිපිම Draw curved arrows to represent the flow of electrons in the reaction on the left Label the reactants on the left as either "Acid" or "Base" (iii) Decide which direction the equilibrium arrows will point in each reaction, based on the given pk, values (a) + H-O H 3-H + (c) H" H + H****H 000 44-00 NH₂ (e) i Дон OH Ө NHarrow_forward
- 3) Label the configuration in each of the following alkenes as E, Z, or N/A (for non-stereogenic centers). 00 E 000 N/A E Br N/A N/A (g) E N/A OH E (b) Oz N/A Br (d) 00 E Z N/A E (f) Oz N/A E (h) Z N/Aarrow_forward6) Fill in the missing Acid, pKa value, or conjugate base in the table below: Acid HCI Approximate pK, -7 Conjugate Base H-C: Hydronium (H₂O') -1.75 H-O-H Carboxylic Acids (RCOOH) Ammonium (NH4) 9.24 Water (H₂O) H-O-H Alcohols (ROH) RO-H Alkynes R--H Amines 25 25 38 HOarrow_forward5) Rank the following sets of compounds in order of decreasing acidity (most acidic to least acidic), and choose the justification(s) for each ranking. (a) OH V SH я вон CH most acidic (lowst pKa) least acidic (highest pKa) Effect(s) Effect(s) Effect(s) inductive effect O inductive effect O inductive effect electronegativity electronegativity O electronegativity resonance polarizability resonance polarizability O resonance O polarizability hybridization Ohybridization O hybridization оarrow_forward
- How negatively charged organic bases are formed.arrow_forwardNonearrow_forward1) For the following molecules: (i) Label the indicated alkenes as either cis (Z), trans (E), or N/A (for non-stereogenic centers) by bubbling in the appropriate label on the molecule. (ii) Complete the IUPAC name located below the structure (HINT: Put the letter of the configuration in parentheses at the beginning of the name!) E z N/A ()-3,4,6-trimethylhept-2-ene E Oz O N/A ()-3-ethyl-1-fluoro-4-methylhex-3-ene E -+- N/A Me )-2,3-dimethylpent-2-ene (d) (b) E O N/A Br ()-5-bromo-1-chloro-3-ethyloct-4-ene ОЕ Z N/A Et (___)-3-ethyl-4-methylhex-3-ene E (f) Oz N/A z N/A HO (4.7)-4-(2-hydroxyethyl)-7-methylnona-4,7-dien-2-onearrow_forward
- O 9:21AM Tue Mar 4 ## 64% Problem 51 of 15 Submit Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s). Be sure to account for all bond-breaking and bond-making steps. H :0: CI. AI :CI: :CI: Cl AI Select to Add Arrows Select to Add Arrows O: Cl :CI: :0: H CI: CI CO Select to Add Arrows Select to Add Arrows :O: CI :0: Cl. 10: AIarrow_forward(i) Draw in the missing lone pair(s) of electrons of the reactants on the left (ii) Draw (curved) arrows to show the flow of electrons in the acid/base reaction on the left (iii) Draw the products of the acid/base on the right (iv) Select the correct label for each product as either "conjugate acid" or "conjugate base" (a) JOH OH NH₂ acid base (b) De "H conjugate acid conjugate acid conjugate base conjugate base acid base conjugate acid conjugate base conjugate acid conjugate base acid basearrow_forwardCould someone answer this NMR and explain please Comment on the general features of the 1H-NMR spectrum of isoamyl ester provided below.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning