Imine hydrolysis is rapid under strongly acidic conditions (H2O,1 equivalent HCI), but imine formation is slow under the same conditions. Provide a reasonable explanation for the observed reactivity. NH +H2O, 1 eq. HCI NH3 FAST NH -H20, 1 eq. HCI NH3 SLOW

Imine hydrolysis is rapid under strongly acidic conditions (H2O,1 equivalent HCI), but imine formation is slow under the same conditions. Provide a reasonable explanation for the observed reactivity. NH +H2O, 1 eq. HCI NH3 FAST NH -H20, 1 eq. HCI NH3 SLOW

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter23: Addition To A Carbonyl

Section: Chapter Questions

Problem 25E

See similar textbooks

Related questions

Q: The weakest of the acids below is and its pK is . The strongest of the acids below is |and its pK is…

A: Pk value - which measure the strength of acid in logarithmic scale.

Q: How will the acid (4-meythyl hexanoic acid) be deprotonated if the pH of the solution is adjusted so…

A: Deprotonation is removal of proton (H+) from acid. At half equivalence point, pH = pKa. The half…

Q: Which amines cannot be prepared by the Gabriel synthesis? Explain your choices.

A: EXPLANATION: The Gabriel Synthesis of primary amines: The Gabriel Synthesis consists of two steps…

Q: Rank the following compounds in order of increasing basicity. NH2 NH2 CONH2

A: Basicity is the ability of a compound to donate electron pair to the other electron deficient…

Q: The powerful electron-withdrawing property of a carbonyl group increases the acidity of a-protons…

A: The electronegativity of the carbonyl group is highest among other functional groups.

Q: Why is acetamide a much weaker base than ammonia? Select one: a. The adjacent C-O makes the lone…

A: Since you have asked multiple questions, we will solve the first question for you. If you want any…

Q: C. Arrange the following compounds in order of decreasing reactivity towards hydrolysis. H2N, H;CO…

A: A multiple choice question based on hydrolysis, which is to be accomplished.

Q: Which compound would be the STRONGEST acid? Select one: O a. CH3CHCICHCICO₂H O b. CICH₂CHCICH₂CO₂H O…

Q: The powerful electron-withdrawing property of a carbonyl group increases the acidity of a-protons…

A: More acidic proton forms more stable carbanion. So, that from this we can find out which is more…

Q: Which amines cannot be prepared by a Gabriel synthesis? Explain your choices. NH2 NH2 NH2 а. b. C.…

A: Gabriel's phthalimide synthesis is used for the conversion of primary alkyl halide into primary…

Q: Draw an arrow pushing mechanism to describe the following reaction. Identify the lewis acid and…

A: Lewis’s acid-base theory: According to the Lewis acid-base theory, the substance that done a lone…

Q: 15. How is an amide converted to an anhydride? Water with strong acid → PCl5 → Carboxylic Acid PCl5…

A: Conversion of amide to anhydride:

Q: 9. Final product? SOc B. 10. Put nitrogens in order of basicity? A. 3>2>1 B. 3>1>2 C. 2>3>1 D. 1>2>3…

Q: Draw the structure of a constitutional isomer of compound B that fits each description. a. an isomer…

A: The given compound is,

Q: Determine which producevthe least basic primary amine 1. NaN3 2.H2/Pd Br А. H2/Pd,C NO2 Br 1.…

Q: Which statement is NOT TRUE regarding compounds W to Z? Ph `NH2 .P. Ph Ph W X Y Z At least one of…

A: Electrophilic - the species which is electrons loving Nucleophile - nucleus loving species Lewis…

Q: Imine hydrolysis is rapid under strongly acidic conditions (H20, 1 equivalent HCI), but imine…

A: Solution: Let see the mechanism of each reaction for the conclusion. In first step pritonation of…

Q: Which compound would be the weakest acid? O CH3CHCICHCICO2H O CHCI2CH2CH2CO2H CH3CCI2CH2CO2H O…

A: minus Inductive effect is directly proportional to acidic character

Q: Rank the following acids in order of increasing(weakest to strongest) acidity. I. 4-methoxybenzoic…

A: ->We can see order of acidity according to order of stability of conjugate base. ->If the…

Q: Why is acetamide a much weaker base than ammonia? Select one: a. The adjacent C-O makes the lone…

A: According to Lewis acid-base concept acids are electron pair acceptors due to vacant orbitals while…

Q: A powerful reducing agent that can reduce all carbonyl groups Sodium borohydride Lithium borohydride…

A: o Lithium aluminium hydride is the strongest reducing agent because of two reasons: 1. Al-H has…

Q: Rank the following compounds in order of increasing acidity of their mostacidic hydrogen atom. (See…

A: The compound C is the least acidic because the electronegativity of nitrogen is less than that of…

Q: Rank the compounds in each group in order of increasing basicity.

A: Basicity- The ability of compound to donate lone pairs of electrons or accept protons is called…

Q: Which of the compounds listed below will produce a slightly basic solution when dissolved into…

A: Here we have to predict for which of the following given salts when dissolved in water the solution…

Q: Explain why the reaction in Problem 18.48 proceeds dramatically more slowly under neutral conditions…

A: The given reaction is,

Q: Rank the following compounds in order of increasing basicity: NH₂ NH₂ NH₂ NH₂ A) B) D) OCH3 NO₂ 2

Q: Which is true regarding the direction of the following reaction? CH3COOH (aq) + H2PO-4 >> CH3COO- +…

Q: regarding nucleophilicity is incorrect.

Q: The powerful electron-withdrawing property of a carbonyl group increases the acidity of a-protons…

Q: Draw the major product of this reaction. Ignore inorganic byproducts and the carboxylic acid side…

A: LiAlH4 is a strong reducing agent . It reduces almost all compounds like Ketone , aldehyde or…

Q: What are the active ions of the ff: a. Tollen's reagent b. Fehling's A c. Fehling's B d.…

A: Since you are asked for multiple sub parts, we are entitled to solve first three questions.

Q: Final step COH OH OEt HN O. ер 11 NH2 OEt 11 Target

A: In this question, you will Identify suitable Reagent / condition for the Final step. You can see…

Q: Match each item to a choice: Choices: alkene Reductive amination Curtius rearrangement Hoffman…

A: Match the following of amine reactions

Q: Amino acids such as glycine are the building blocks of large molecule.called proteins that give…

A: a) Since in the structure of glycine we can see that there is a N with lone pair electron and an…

Q: Arrange each group of compounds in order of increasing acidity.(b) p-toluenesulfonic acid, acetic…

A: (b) Given acids, p-toluenesulfonic acid, acetic acid, and chloroacetic acid

Q: Rank the dicarbonyl compounds in order of increasing acidity. (least acidic list first) B A< B< C B<…

A: This question is related to basic concept of chemistry. First we will deprotonate the given…

Q: Draw the major product of this reaction. Ignore inorganic byproducts and the amine side product. N'…

A: Given reaction is : Draw the major product of the reaction = ?

Q: A) In the boxes provided, rank the following in order of basicity (ability to react with H*). 1 =…

A: More stable anion have less basic character and less stable anion have more basic character

Q: (i) Explain why pyrrole is a much stronger acid ammonia. pKa = 15 %3D H* pKa 36 NH3 "NH, + H* Would…

A: Solution : Pyrrole has exceptional strong acidic property due to the participation of lone pair of…

Q: -NH3 NH3 но- -NH3 H3C- -NH3 I II III IV

A: Acidity completely depends on the stability of conjugate base of that acid. If it is most stable…

Q: 5.3. The following enamine is in equilibrium with which compounds when in trace acidic conditions?…

A: The enamine is in equilibrium with its imine form in presence of trace acidic conditions.

Q: Within each structure, rank the indicated nitrogens by increasing basicity. Explain all (guide line:…

A: According to Q&A guidelines of Bartleby, we are supposed to answer only the first question out…

Q: Q1- From a-haloketone how can you prepared flowing compounds : Imidazole Oxazole…

Q: C. Arrange the following compounds in order of decreasing reactivity towards hydrolysis. H2N. H,CO…

A: In this question, we will arranged all compounds in decreasing order of their reactivity. You can…

Q: ompound that is most easily hydrolyzed by acid in water `NH А. В. C. D.

A: Hydrolysis is breaking of oxygen of NH linkage with help of H20 molecule in presence of acid H+.

Q: Rank the compounds in order of basicity. Most basic Least basic Answer Bank 3-chloropyridine…

Q: H2PO4- is amphoteric. Which of the following will be the product in the acid-base reaction where…

Q: Show how acid derivatives hydrolyze to carboxylic acids under either acidic or basicconditions.…

Q: e. Baco: +2H:0 (aq) Ba (aq) + H2CO:(aq) +2H:0() f The basic dissociation of aniline, C.H:NH2 g. The…

A: Equilibrium Constant:- The equilibrium constant of a chemical reaction is basically its reaction…

Q: Rank the nitrogens below in order of decreasing basicity (most basic to least basic) NH (c) (a) (b)…

A: The answer is given as follows Basicity order is c>a>b

Concept explainers

Aldehydes and Ketones

Aldehydes and ketones are organic compounds that have a carbonyl group, C = O, as their functional group. They both differ in the placement of this carbonyl group in their structures.

Question

Imine hydrolysis is rapid under strongly acidic conditions (H2O, 1 equivalent HCI), but imine
formation is slow under the same conditions. Provide a reasonable explanation for the
observed reactivity.
NH
+H2O, 1 eq. HCI
NH3
FAST
NH
-H20, 1 eq. HCI
NH3
SLOW

Expert Solution

This question has been solved!

Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.

This is a popular solution!

SEE SOLUTION Check out a sample Q&A here

Step 1

VIEW

Step 2

VIEW

Trending now

This is a popular solution!

Step by step

Solved in 2 steps with 1 images

SEE SOLUTION Check out a sample Q&A here

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

Show how acid derivatives hydrolyze to carboxylic acids under either acidic or basicconditions. Explain why some acid derivatives (amides, for example) require muchstronger conditions for hydrolysis than other derivatives.
Rank the following compounds in order of increasing basicity: CH3O- , H2N- , H2O and NH3
Hypoglycin A, an amino acid derivative found in unripened lychee, is anacutely toxic compound that produces seizures, coma, and sometimesdeath in undernourished children when ingested on an empty stomach. (a) Draw the neutral, positively charged, and negatively charged forms of hypoglycin A. (b) Which form predominates at pH = 1, 6, and 11? (c) What is the structure of hypoclycin A at its isoelectric point?
The following three derivatives of succinimide are anticonvulsants that have found use in the treatment of epilepsy, particularly petit mal seizures. Q. Show how this same synthetic strategy can be used to prepare ethosuximide and methsuximide.
Triethylenemelamine (TEM) is an antitumor agent. Its activity is due to its ability to cross-link DNA. a. Explain why it can be used only under slightly acidic conditions. b. Explain why it can cross-link DNA.
Triethylenemelamine (TEM) is an antitumor agent. Its activity is due to its ability to cross-link DNA. a. Explain why it can be used only under slightly acidic conditions.b. Explain why it can cross-link DNA.
Rank the attached compounds in order of increasing basicity andexplain the order you chose.
based on this video: on Hinsberg Test Tests for Amines - MeitY OLabs (8.5min) https://www.youtube.com/watch?v=j5jgMUWri8U Write the reaction (two-step, in skeletal) of each test amine when tested in the Hinsberg Test.
As far back as the 16th century, South American Incas chewed the leaves of the coca bush, Erythroxylon coca, to combat fatigue. Chemical studies of Erythroxylon coca by Friedrich WĂ¶hler in 1862 resulted in the discovery of cocaine, C17H21NO4, as the active component. Basic hydrolysis of cocaine leads to methanol, benzoic acid, and another compound called ecgonine, C9H15NO3. Oxidation of ecgonine with CrO3 yields a keto acid that readily loses CO2 on heating, giving tropinone. (a) What is a likely structure for the keto acid? (b) What is a likely structure for ecgonine, neglecting stereochemistry? (c) What is a likely structure for cocaine, neglecting stereochemistry?
Rank the attached compounds in order of increasing basicity.
The reaction of an ester with an amine is not as slow as the reaction of an ester with water or an alcohol. Explain with reason. Explain why the rate of aminolysis of an ester cannot be increased by H+, OH- or OR-. How can you activate the carboxylic acid? Is acid catalyzed hydrolysis of acetamide a reversible or an irreversible reaction. Explain.
(Give clear handwritten solution) which transformation is produce strong base In clonixin. Select and explain!