Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 9.8, Problem 32P
After a proton is removed from the OH group, which compound in each pair forms a cyclic ether more rapidly?
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
9. Which below is the keto form?
Which below is the enol form?
OH
OH
OH
I
II
III
IV
Which of the following reactions are correct? Explain the answer.
+ H₂O
+ H₂O
H₂SO4
H OH
H
OH
7. For compound A in acid, it is the hydroxyl that is protonated
to a greater extent than the carbonyl oxygen. However, for
compound B in acid, it is the carbonyl oxygen that is
protonated to a greater extent than the hydroxyl oxygen.
Explain this difference.
H2SO4
ОН
ОН2
ОН
H2SO4
ОН
ОН
Chapter 9 Solutions
Organic Chemistry
Ch. 9.1 - Prob. 3PCh. 9.1 - Does increasing the energy barrier for an SN2...Ch. 9.1 - Rank the following alkyl bromides from most...Ch. 9.2 - Prob. 8PCh. 9.2 - Prob. 9PCh. 9.2 - Prob. 10PCh. 9.2 - Prob. 11PCh. 9.2 - Which substitution reaction lakes place more...Ch. 9.2 - Prob. 14PCh. 9.2 - Prob. 16P
Ch. 9.3 - Prob. 17PCh. 9.4 - Prob. 18PCh. 9.5 - Prob. 19PCh. 9.5 - Prob. 20PCh. 9.5 - Prob. 21PCh. 9.5 - Prob. 22PCh. 9.6 - Prob. 23PCh. 9.6 - Prob. 24PCh. 9.6 - Which of the following reactions take place more...Ch. 9.7 - Prob. 26PCh. 9.7 - Prob. 27PCh. 9.7 - Prob. 28PCh. 9.7 - Prob. 30PCh. 9.7 - Under which of the following reaction conditions...Ch. 9.8 - After a proton is removed from the OH group, which...Ch. 9.8 - Prob. 33PCh. 9.9 - Prob. 34PCh. 9 - Prob. 1PCh. 9 - Methoxychlor is an insecticide that was intended...Ch. 9 - Prob. 35PCh. 9 - Prob. 36PCh. 9 - Prob. 37PCh. 9 - Prob. 38PCh. 9 - Prob. 39PCh. 9 - Prob. 40PCh. 9 - Starting with cyclohexene, how can the following...Ch. 9 - Prob. 42PCh. 9 - The pKa of acetic acid in water is 4.76. What...Ch. 9 - Prob. 44PCh. 9 - Prob. 45PCh. 9 - Prob. 46PCh. 9 - Prob. 47PCh. 9 - Prob. 48PCh. 9 - Prob. 49PCh. 9 - Prob. 50PCh. 9 - Prob. 51PCh. 9 - tert-Butyl chloride undergoes solvolysis in both...Ch. 9 - Prob. 53PCh. 9 - Prob. 54PCh. 9 - In which solventethanol or diethyl etherwould the...Ch. 9 - Prob. 56PCh. 9 - Two bromoethers are obtained from the reaction of...Ch. 9 - Prob. 58PCh. 9 - Prob. 59PCh. 9 - Prob. 60PCh. 9 - Propose a mechanism for the following reaction:Ch. 9 - Prob. 62PCh. 9 - Prob. 63PCh. 9 - Prob. 64PCh. 9 - Prob. 65PCh. 9 - When equivalent amounts of methyl bromide nod...Ch. 9 - Prob. 67PCh. 9 - The reaction of chloromethane with hydroxide ion...
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
- Rank the following compounds in order of increasing reactivity in a substitution reaction with −CN as nucleophile.arrow_forwardDenote how many nucleophilic centers are present in the following molecular structure (in case of polar bonds show clearly on the structure the dipoles õ+ and d-). :o: сноarrow_forwardb) The Wolf-Kishner reduction is a reaction used in Organic Chemistry to convert carbonyl functionalities into methylene group. The reaction was used to convert an aldehyde or ketone to an alkane using hydrazine, base and thermal conditions. The mechanism begins with the attack of hydrazine of the aldehyde or ketone. Stage 1: The reaction of aldehyde/ketone with hydrazine to produce hydrazine Stage 2: Reaction with the base and heat to convert hydrozone to alkane Write the mechanism of the reaction.arrow_forward
- This question is about the reaction scheme shown. CH₂ CH₂ step 2 step 1 NO₂ NH₂ NHCOCK, Amine A CH₂CI step 4 step 5 Amine B State the reagents needed for step 1 and the reagents needed for step 2. step 1 step 2 Give the name of the mechanism for the reaction in step 3. CH₂ CHÍNH, step 3arrow_forward3A Complete the reactions below. H₂SO4/H₂O HgSO4 A NaBH4 EtOH B лH₂SO4 Carrow_forwardWhich compound is the strongest base? NH2 NH2 NH2 NH2 `NH2 O2N III IV V II O V O II O IVarrow_forward
- When cyclohexene is reacted with hydrobromic acid in acetic acid, the major product is bromocyclohexane. There is a small amount of cyclohexyl acetate formed. What is the mechanism that forms both compounds? What is the purification procedure that isolates both compounds?arrow_forwardIn a base catalyzed keto-enol tautomerization of an aldehyde the first step of the mechanism is removal of the proton from the alpha carbon. removal for a proton from the carbonyl carbon. protonation of the carbonyl carbon. protonation of the carbonyl oxygen.arrow_forwardNonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forward
- An ion with a positively charged nitrogen atom in a three-membered ring is called an aziridinium ion. The following aziridinium ion reacts with sodiummethoxide to form compounds A and B: If a small amount of aqueous Br2 is added to A, the reddish color of Br2 persists, but the color disappears when Br2 is added to B. When the aziridinium ion reacts with methanol, only A is formed. Identify A and B.arrow_forwardRank the reactivity of the compounds below toward nucleophilic acyl substitution by writing the compounds' letters in the proper blanks in the box below. `NH CI Br CH3 CH3 A В C E rank compounds for acyl substitution reactivity most least reactive reactivearrow_forwardThe reaction of the carbonyl compound with cyanide yields The R-isomer The S-isomer Both the R and S isomer None of the above Adding NaCN to the carbonyl compound poses the risk of making HCN, which is poisonous. How can this risk be mitigated? Add NaOH first, then NaCN Add NaCN first, then NaOH Add NaHSO3 first, then NaCN Add NaOH first, then NaHSO3arrow_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: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
IR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=_TmevMf-Zgs;License: Standard YouTube License, CC-BY