EBK ORGANIC CHEMISTRY
9th Edition
ISBN: 8220102744097
Author: 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
Predict the product of this organic reaction:
IZ
+
HO
i
P+H₂O
Specifically, in the drawing area below draw the skeletal ("line") structure of P.
If there is no reasonable possibility for P, check the No answer box under the drawing area.
No Answer
Click and drag to start drawing a
structure.
☐ :
Predict the products of this organic reaction:
0
O
-----
A
+ KOH ?
CH3-CH2-C-O-CH2-C-CH3
Specifically, in the drawing area below draw the condensed structure of the product, or products, of this reaction. (If there's more than one product, draw them
in any arrangement you like, so long as they aren't touching.)
If there aren't any products because this reaction won't happen, check the No reaction box under the drawing area.
No reaction
Click anywhere to draw the first
atom of your structure.
X
⑤
è
Predict the products of this organic reaction:
O
CH3
+ H2O + HCI A
A?
CH3-CH2-C-N-CH3
Specifically, in the drawing area below draw the condensed structure of the product, or products, of this reaction. If there's more than one product, draw them
in any arrangement you like, so long as they aren't touching.
If there aren't any products because this reaction won't happen, check the No reaction box under the drawing area.
No Reaction
Click anywhere to draw the first
atom of your structure.
Chapter 11 Solutions
EBK 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
- What is the missing reactant in this organic reaction? R+ HO-C-CH2-CH3 0= CH3 CH3 —CH, C−NH—CH CH3 + H₂O Specifically, in the drawing area below draw the condensed structure of R. If there is more than one reasonable answer, you can draw any one of them. If there is no reasonable answer, check the No answer box under the drawing area. Note for advanced students: you may assume no products other than those shown above are formed. No Answer Click anywhere to draw the first atom of your structure. €arrow_forward个 CHEM&131 9267 - $25 - Intro to Mail - Hutchison, Allison (Student x Aktiv Learnin https://app.aktiv.com Draw the product of the reaction shown below. Ignore inorganic byproducts. + Na2Cr2O7 Acetone, H2SO4 Type here to search Dryng OH W Prarrow_forwardPredict the products of this organic reaction: OH + NaOH A? Specifically, in the drawing area below draw the skeletal ("line") structure of the product, or products, of this reaction. (If there's more than one product, draw them in any arrangement you like, so long as they aren't touching.) If there aren't any products because this reaction won't happen, check the No reaction box under the drawing area. No reaction Click and drag to start drawing a structure. ✓ Sarrow_forward
- Predict the products of this organic reaction: CH3-C-O-CH2-CH2-C-CH3 + H₂O ? A Specifically, in the drawing area below draw the condensed structure of the product, or products, of this reaction. (If there's more than one product, draw them in any arrangement you like, so long as they aren't touching.) If there aren't any products because this reaction won't happen, check the No reaction box under the drawing area. No reaction Click anywhere to draw the first atom of your structure. :☐ darrow_forwardDE d. Draw an arrow pushing mechanism for the following IN O CI N fo 人 P Polle DELL prt sc home end ins F5 F6 F7 F8 F9 F10 F11 F12arrow_forwardPredict the products of this organic reaction: + H₂O H* ? A Specifically, in the drawing area below draw the skeletal ("line") structure of the product, or products, of this reaction. (If there's more than one product, draw them in any arrangement you like, so long as they aren't touching.) If there aren't any products because this reaction won't happen, check the No reaction box under the drawing area. No Reaction Click and drag to start drawing a structure.arrow_forward
- Predict the major organic products of the reaction below and draw them on right side of the arrow. If there will be no significant reaction, check the box below the drawing area instead. C Cl CH, OH There will be no significant reaction. + pyridine G Click and drag to start drawing a structure.arrow_forwardWhat is the missing reactant in this organic reaction? H R+ H2O Δ OH 0= CH3-CH-O-CH3 + CH3-C-OH Specifically, in the drawing area below draw the condensed structure of R. If there is more than one reasonable answer, you can draw any one of them. If there is no reasonable answer, check the No answer box under the drawing area. No Answer Click anywhere to draw the first atom of your structure. dyarrow_forwardYou are trying to determine whether the following organic reaction can be done in a single synthesis step. If so, add any missing reagents or conditions in the drawing area below. If it isn't possible to do this reaction in a single synthesis step, check the box below the drawing area instead. Note for advanced students: if you have a choice of reagents to add, you should choose the least reactive and most economical reagents possible. Cl It isn't possible to do this reaction in a single synthesis step. + T OHarrow_forward
- Predict the products of this organic reaction: CH3 O CH3-CH-C-O-CH2-CH2-CH3 + H₂OH+ Η ? A Specifically, in the drawing area below draw the condensed structure of the product, or products, of this reaction. (If there's more than one product, draw them in any arrangement you like, so long as they aren't touching.) If there aren't any products because this reaction won't happen, check the No reaction box under the drawing area. No Reaction Click anywhere to draw the first atom of your structure.arrow_forward€ CH3-CH-C-O-CH2-CH2-CH3 + NaOH A? Specifically, in the drawing area below draw the condensed structure of the product, or products, of this reaction. (If there's more than one product, draw them in any arrangement you like, so long as they aren't touching.) If there aren't any products because this reaction won't happen, check the No reaction box under the drawing area. Predict the products of this organic reaction: CH3 O Click anywhere to draw the first atom of your structure. No reaction ✓ Garrow_forwardA molecule can have a temporary or permanent depending on the structure and the way the electrons can move. True Falsearrow_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