
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
tab
esc
く
Drawing the
After running various experiments, you determine that the mechanism for the following reaction occurs in a step-wise fashion.
Br
+
OH
+
Using this information, draw the correct mechanism in the space below.
1
Explanation
Check
F2
F1
@2
Q
W
A
os lock
control
option
T
S
#
3
80
F3
Br
$
4
0105
%
OH2
+
Br
Add/Remove step
X
C
F5
F6
6
R
E
T
Y
29
&
7
F
D
G
H
Click and drag to start
drawing a structure.
© 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Ce
A
F7
DII
F8
C
Ո
8 *
9
4
F10
F
C
J
K
L
C
V
Z
X
B
N
M
H
command
P
ge
Co
Indicate compound A that must react with ethylbenzene to obtain 4-ethylbenzene-1-sulfonic acid.
3-bromo-4-ethylbenzene-1-sulfonic acid.
Part 1 of 2
Draw the structure of A, the minor E1 product of the reaction.
esc
I
Skip Part
Check
H₂O, D
2
A
+
Click and drag to start drawing a
structure.
-0-
F1
F2
1
2
#
3
Q
A
80
F3
W
E
S
D
F4
$
4
%
5
F5
ㅇ
F6
R
T
Y
F
G
X
5
&
7
+
Save
2025 McGraw Hill LLC. All Rights Reserved.
DII
F7
F8
H
*
C
80
J
Z
X
C
V
B
N
4
F9
6
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
- File Preview The following is a total synthesis of the pheromone of the western pine beetle. Such syntheses are interesting both because of the organic chemistry, and because of the possibility of using species specific insecticides, rather than broad band insecticides. Provide the reagents for each step. There is some chemistry from our most recent chapter in this synthesis, but other steps are review from earlier chapters. (8 points) COOEt COOEt A C COOEt COOEt COOH B OH OTS CN D E See the last homework set F for assistance on this one. H+, H₂O G OH OH The last step is just nucleophilic addition reactions, taking the ketone to an acetal, intramolecularly. But it is hard to visualize the three dimensional shape as it occurs. Frontalin, pheromone of the western pine beetlearrow_forwardFor the reaction below: 1. Draw all reasonable elimination products to the right of the arrow. 2. In the box below the reaction, redraw any product you expect to be a major product. C Major Product: Check + ◎ + X ง © Cl I F2 80 F3 I σ F4 I F5 NaOH Click and drawing F6 A 2025 McGraw Hill LLC. All Rights E F7 F8 $ # % & 2 3 4 5 6 7 8 Q W E R T Y U A S D F G H Jarrow_forwardCan I please get help with this graph. If you can show exactly where it needs to pass through.arrow_forward
- N Draw the major product of this reaction. Ignore inorganic byproducts. D 1. H₂O, pyridine 2. neutralizing work-up V P W X DE CO e C Larrow_forwardDraw the major product of this reaction. Ignore inorganic byproducts. N O' 1. H2O, pyridine 2. neutralizing work-up く 8 W aarrow_forwardIdeal Gas Law Practice Name If you need a refresher on Ideal Gas Law, go back to your Ideal Gas Law Reading Assignment from last week! On all of the following, you'll need to make sure to convert pressures to atm and convert temperatures to Kelvin in order to be able to use the R gas constant on your equation sheet! Given: Ideal Gas Law = then P= pressure V = volume R= ideal gas consent PV=nRT namount of substance n=PV/TR P=nRT/V I = temperature V=nRT/P T=PV/nR R=PV/nT 1. What pressure is required to contain 0.023 moles of nitrogen gas in a 4.2 L container at a temperature of 20.°C? 2. Oxygen gas is collected at a pressure of 123 kPa in a container which has a volume of 10.0 L. What temperature must be maintained on 0.500 moles of this gas in order to maintain this pressure? Express the temperature in degrees Celsius. 3. How many moles of chlorine gas would occupy a volume of 35.5 L at a pressure of 100.0 kPa and a temperature of 100. °C? After determining the number of moles,…arrow_forward
- 1. The following conversion includes chemistry we have covered very recently, some chemistry from last term, and chemistry from the first chapter of this unit. Provide curly arrows and an explanation for this mechanism. Use the reagents in the order given. You do not need any other reagents. 1. NaOEt OEt 2.arrow_forwardCOOEt COOEt Step 1 Step 2 Step 3 COOEt COOEt COOH Step 6 OH Step 4 Step 7 (racemic) cyclizes under conditions (8) OTS Step 5 Step 8 ОН OH (racemic) Frontalin (racemic) Shown above are the steps in one of the several published syntheses of Frontalin, a pheromone of the western pine beetle. From the choices provided, show the reagents and conditions by which step 3 of this synthesis might be accomplished. List the reagent(s) in order that will accomplish this transformation. No more than 4 steps are required. List your answer as a single letter (single-step transformation) or a series of letters (multi-step transformation) with no commas separating them. For example, "ab" corresponds to: 1. Eto Na+ 2. NaOH, H₂O NOTE: The order in which you list your letters matters! Reagents: a. Eto Na* g. NaCN b. NaOH, H₂O h. SOCI₂ c. H3O+, heat i. (CH3)2CuLi, ether, -78°C d. LiAlH4 j. H₂O e. p-TsCI, pyridine k. RCO3H f. Br I. H3O+ 1,024arrow_forwardK ← nationa Login - Paymentivet MapQue Draw the major product of this reaction. Ignore inorganic byproducts and the carboxylic acid side product. N 1. excess LiAlH4 2. H₂O ✓ W aarrow_forward
- Draw the major product of this reaction. Ignore inorganic byproducts and the alcohol side product. 1. H3O+, heat 2. Neutralizing work-up Drawing Qarrow_forwardIndicate the procedure (reagent Z) to go from compound A1 to compound A2. A1 Z P(C6H5)3 A2arrow_forwardPlease help with this graph.arrow_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