
Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Question
Chapter 16.8, Problem 32P
(a)
Interpretation Introduction
Interpretation:
The mechanisms for the following reactions should be determined.
- 1. The acid-base catalyzed hydrolysis of an imine to a carbonyl compound and a primary
amine . - 2. The acid-base catalyzed hydrolysis of an enamine to a carbonyl compounds and a secondary amine.
Concept introduction:
The chemical compound containing carbon and nitrogen double bond is known as imine.
Enamine is derived by the condensation of an
(b)
Interpretation Introduction
Interpretation:
The reason for the difference in mechanism of two reactions should be given.
Concept introduction:
The chemical compound containing carbon and nitrogen double bond is known as imine.
Enamine is derived by the condensation of an aldehyde and ketone with secondary amine.
Expert Solution & Answer

Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Assign these C-NMR and H-NMR Spectrum
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
Chapter 16 Solutions
Organic Chemistry (8th Edition)
Ch. 16.1 - Give two names for each of the following:Ch. 16.1 - Prob. 2PCh. 16.1 - Name the following:Ch. 16.2 - Prob. 4PCh. 16.4 - What products are formed when the following...Ch. 16.4 - We saw on the previous page that...Ch. 16.4 - a. How many stereoisomers are obtained from the...Ch. 16.4 - Prob. 9PCh. 16.4 - Write the mechanism for the reaction of acetyl...Ch. 16.4 - Prob. 11P
Ch. 16.4 - Show how the following compounds can be...Ch. 16.4 - Prob. 13PCh. 16.4 - Prob. 14PCh. 16.4 - In the mechanism for cyanohydrin formation, why is...Ch. 16.4 - Prob. 16PCh. 16.4 - Prob. 17PCh. 16.4 - Show two ways to convert an alkyl halide into a...Ch. 16.5 - Prob. 20PCh. 16.5 - Prob. 21PCh. 16.5 - Prob. 22PCh. 16.5 - Prob. 23PCh. 16.6 - Prob. 24PCh. 16.7 - What reducing agents should be used to obtain the...Ch. 16.7 - Prob. 26PCh. 16.8 - Prob. 27PCh. 16.8 - Prob. 28PCh. 16.8 - Prob. 29PCh. 16.8 - The pKa of protonated acetone is about 7.5. and...Ch. 16.8 - Prob. 31PCh. 16.8 - Prob. 32PCh. 16.8 - Prob. 33PCh. 16.8 - Excess ammonia must be used when a primary amine...Ch. 16.8 - The compounds commonly known as amino acids are...Ch. 16.9 - Hydration of an aldehyde is also catalyzed by...Ch. 16.9 - Which ketone forms the most hydrate in an aqueous...Ch. 16.9 - When trichloroacetaldehyde is dissolved in water,...Ch. 16.9 - Which of the following are a. hermiacetals? b....Ch. 16.9 - Prob. 40PCh. 16.9 - Explain why an acetal can be isolated but most...Ch. 16.10 - Prob. 42PCh. 16.10 - Prob. 43PCh. 16.10 - What products would be formed from the proceedings...Ch. 16.10 - a. In a six-step synthesis, what is the yield of...Ch. 16.10 - Show how each of the following compounds could be...Ch. 16.12 - Prob. 47PCh. 16.13 - Prob. 49PCh. 16.14 - Prob. 50PCh. 16.15 - Prob. 51PCh. 16.16 - Prob. 52PCh. 16 - Draw the structure for each of the following: a....Ch. 16 - Prob. 54PCh. 16 - Prob. 55PCh. 16 - Prob. 56PCh. 16 - a. Show the reagents required to form the primary...Ch. 16 - Prob. 58PCh. 16 - Prob. 59PCh. 16 - Using cyclohexanone as the starting material,...Ch. 16 - Propose a mechanism for each of the following...Ch. 16 - Show how each of the following compounds can be...Ch. 16 - Fill in the boxes:Ch. 16 - Prob. 64PCh. 16 - Identify A through O:Ch. 16 - Prob. 66PCh. 16 - Prob. 67PCh. 16 - Prob. 68PCh. 16 - How many signals would the product of the...Ch. 16 - Prob. 70PCh. 16 - Prob. 71PCh. 16 - Prob. 72PCh. 16 - Prob. 73PCh. 16 - Prob. 74PCh. 16 - Prob. 75PCh. 16 - Prob. 76PCh. 16 - Prob. 77PCh. 16 - Prob. 78PCh. 16 - Draw structure for A-D for each of the following:Ch. 16 - Prob. 80PCh. 16 - a. Propose a mechanism for the following reaction:...Ch. 16 - Prob. 82PCh. 16 - A compound gives the following IR spectrum. Upon...Ch. 16 - How can be following compounds be prepared from...Ch. 16 - Prob. 85PCh. 16 - Prob. 86PCh. 16 - Prob. 87PCh. 16 - In the presence of an acid catalyst, acetaldehyde...Ch. 16 - Prob. 89PCh. 16 - Prob. 90PCh. 16 - Prob. 91PCh. 16 - A compound reacts with methylmagnesium bromide...Ch. 16 - Show how each of the following compounds can be...Ch. 16 - Prob. 94PCh. 16 - The pKa values of the carboxylic acid groups of...Ch. 16 - The Baylis-Hillman reaction is a DABCO...Ch. 16 - Prob. 97PCh. 16 - Prob. 98P
Knowledge Booster
Similar questions
- 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.arrow_forwardWhat 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_forward
- Predict 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_forwardPredict 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_forward
- Predict 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_forwardPredict 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_forward
- You 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_forwardPredict 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_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
- Chemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning

Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning

Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning


Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning