Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)
Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)
2nd Edition
ISBN: 9780393655551
Author: KARTY, Joel
Publisher: W. W. Norton & Company
Question
Book Icon
Chapter 19, Problem 19.54P
Interpretation Introduction

(a)

Interpretation:

The product of the given reaction is to be predicted, considering one molar equivalent of H2 reacts.

Concept introduction:

The C=C functional group of an alkene or the CC functional group of an alkyne can be removed via catalytic hydrogenation. Catalytic hydrogenation is a reaction in which H2 adds to a molecule in the presence of a metal catalyst such as Pt, Pd, or Ni. Catalytic hydrogenation readily reduces an alkene or an alkyne to an alkane. The reduction of an alkyne to an alkene via catalytic hydrogenation favors production of the cis isomer over the trans. Catalytic hydrogenation using a poisoned catalyst (a Lindlar catalyst) reduces an alkyne to a cis alkene. The functional groups in alkenes, alkynes, and aldehydes can be selectively reduced over those in ketones, nitriles, and amides.

Expert Solution
Check Mark

Answer to Problem 19.54P

The product of the given reaction is

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second), Chapter 19, Problem 19.54P , additional homework tip  1

Explanation of Solution

The given reaction is

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second), Chapter 19, Problem 19.54P , additional homework tip  2

The given reaction condition correlates to catalytic hydrogenation; it reduces alkene’s C=C over ketone’s C=O. Thus, the H2 molecule added over the C=C double bond converts the C=C double bond to C-C single bond.

Therefore, the product of the given reaction is

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second), Chapter 19, Problem 19.54P , additional homework tip  3

Conclusion

The product of the given reaction is predicted using the given reaction conditions.

Interpretation Introduction

(b)

Interpretation:

The product of the given reaction is to be predicted, considering one molar equivalent of H2 reacts.

Concept introduction:

The C=C functional group of an alkene or the CC functional group of an alkyne can be removed via catalytic hydrogenation. Catalytic hydrogenation is a reaction in which H2 adds to a molecule in the presence of a metal catalyst such as Pt, Pd, or Ni. Catalytic hydrogenation readily reduces an alkene or an alkyne to an alkane. The reduction of an alkyne to an alkene via catalytic hydrogenation favors production of the cis isomer over the trans. Catalytic hydrogenation using a poisoned catalyst (a Lindlar catalyst) reduces an alkyne to a cis alkene. The functional groups in alkenes, alkynes, and aldehydes can be selectively reduced over those in ketones, nitriles, and amides.

Catalytic hydrogenation is more favored at a less sterically hindered multiple bond than at a more sterically hindered one.

Expert Solution
Check Mark

Answer to Problem 19.54P

The product of the given reaction is

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second), Chapter 19, Problem 19.54P , additional homework tip  4

Explanation of Solution

The given reaction

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second), Chapter 19, Problem 19.54P , additional homework tip  5

The given reaction condition correlates to catalytic hydrogenation. The substrate in the given reaction have two sites for catalytic hydrogenation, one C=C bond and another CC bond.

Catalytic hydrogenation is more favored at a less sterically hindered multiple bond than at a more sterically hindered one.

In the given reaction, the C=C bond is sterically less hindered; therefore the H2 molecule adds over the C=C double bond and converts the double bond to single bond. Therefore, the product of the given reaction is

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second), Chapter 19, Problem 19.54P , additional homework tip  6

Conclusion

The product of the given reaction is predicted using given reaction conditions.

Interpretation Introduction

(c)

Interpretation:

The product of the given reaction is to be predicted, considering one molar equivalent of H2 reacts.

Concept introduction:

The C=C functional group of an alkene or the CC functional group of an alkyne can be removed via catalytic hydrogenation. Catalytic hydrogenation is a reaction in which H2 adds to a molecule in the presence of a metal catalyst such as Pt, Pd, or Ni. Catalytic hydrogenation readily reduces an alkene or an alkyne to an alkane. The reduction of an alkyne to an alkene via catalytic hydrogenation favors production of the cis isomer over the trans. Catalytic hydrogenation using a poisoned catalyst (a Lindlar catalyst) reduces an alkyne to a cis alkene. The less sterically hindered C=C or triple bond is selectively reduced.

Expert Solution
Check Mark

Answer to Problem 19.54P

The product of the given reaction is

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second), Chapter 19, Problem 19.54P , additional homework tip  7

Explanation of Solution

The given reaction is

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second), Chapter 19, Problem 19.54P , additional homework tip  8

The given reaction condition correlates to catalytic hydrogenation. The substrate in the given reaction have two sites for catalytic hydrogenation, two C=C bonds.

Catalytic hydrogenation is more favored at a less sterically hindered multiple bond than at a more sterically hindered one.

In the given reaction, the C=C bond is at bottom is sterically less hindered; therefore the H2 molecule adds over the C=C double bond and converts the double bond to a single bond. Therefore, the product of the given reaction is

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second), Chapter 19, Problem 19.54P , additional homework tip  9

Conclusion

The product of the given reaction is predicted using the given reaction conditions.

Interpretation Introduction

(d)

Interpretation:

The product of the given reaction is to be predicted, considering one molar equivalent of H2 reacts.

Concept introduction:

The C=C functional group of an alkene or the CC functional group of an alkyne can be removed via catalytic hydrogenation. Catalytic hydrogenation is a reaction in which H2 adds to a molecule in the presence of a metal catalyst such as Pt, Pd, or Ni. Catalytic hydrogenation readily reduces an alkene or an alkyne to an alkane. The reduction of an alkyne to an alkene via catalytic hydrogenation favors production of the cis isomer over the trans. Catalytic hydrogenation using a poisoned catalyst (a Lindlar catalyst) reduces an alkyne to a cis alkene. The functional groups in alkenes, alkynes, and aldehydes can be selectively reduced over those in ketones, nitriles, and amides.

Expert Solution
Check Mark

Answer to Problem 19.54P

The product of the given reaction is

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second), Chapter 19, Problem 19.54P , additional homework tip  10

Explanation of Solution

The given reaction is

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second), Chapter 19, Problem 19.54P , additional homework tip  11

The given reaction condition correlates to catalytic hydrogenation. The substrate in the given reaction has two sites for catalytic hydrogenation, one CC bond and another the amide group.

The functional groups in alkenes, alkynes, and aldehydes can be selectively reduced over those in ketones, nitriles, and amides. Thus, the H2 molecule is added over the CC triple bond. Catalytic hydrogenation using a poisoned catalyst (a Lindlar catalyst) reduces an alkyne to a cis alkene, as one molar equivalent of H2 reacts.

Therefore, the product of the given reaction is

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second), Chapter 19, Problem 19.54P , additional homework tip  12

Conclusion

The product of the given reaction is predicted using the given reaction conditions.

Interpretation Introduction

(e)

Interpretation:

The product of the given reaction is to be predicted, considering one molar equivalent of H2 reacts.

Concept introduction:

The C=C functional group of an alkene or the CC functional group of an alkyne can be removed via catalytic hydrogenation. Catalytic hydrogenation is a reaction in which H2 adds to a molecule in the presence of a metal catalyst such as Pt, Pd, or Ni. Catalytic hydrogenation readily reduces an alkene or an alkyne to an alkane. The reduction of an alkyne to an alkene via catalytic hydrogenation favors production of the cis isomer over the trans. Catalytic hydrogenation using a poisoned catalyst (a Lindlar catalyst) reduces an alkyne to a cis alkene. The functional groups in alkenes, alkynes, and aldehydes can be selectively reduced over those in ketones, nitriles, and amides.

Expert Solution
Check Mark

Answer to Problem 19.54P

The product of the given reaction is

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second), Chapter 19, Problem 19.54P , additional homework tip  13

Explanation of Solution

The given reaction is

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second), Chapter 19, Problem 19.54P , additional homework tip  14

The given reaction condition correlates to catalytic hydrogenation. The substrate in the given reaction has two sites for catalytic hydrogenation, one C=C bond and another the nitrile group.

The functional group ketones can be selectively reduced over nitriles. Thus, the H2 molecule is added over the C=O double bond and converted to the OH (alcoholic group).

Therefore, the product of the given reaction is

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second), Chapter 19, Problem 19.54P , additional homework tip  15

Conclusion

The product of the given reaction is predicted using the given reaction conditions.

Interpretation Introduction

(f)

Interpretation:

The product of the given reaction is to be predicted, considering one molar equivalent of H2 reacts.

Concept introduction:

The C=C functional group of an alkene or the CC functional group of an alkyne can be removed via catalytic hydrogenation. Catalytic hydrogenation is a reaction in which H2 adds to a molecule in the presence of a metal catalyst such as Pt, Pd, or Ni. Catalytic hydrogenation readily reduces an alkene or an alkyne to an alkane. The reduction of an alkyne to an alkene via catalytic hydrogenation favors production of the cis isomer over the trans. Catalytic hydrogenation using a poisoned catalyst (a Lindlar catalyst) reduces an alkyne to a cis alkene.

Expert Solution
Check Mark

Answer to Problem 19.54P

The product of the given reaction is

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second), Chapter 19, Problem 19.54P , additional homework tip  16

Explanation of Solution

The given reaction is

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second), Chapter 19, Problem 19.54P , additional homework tip  17

The given reaction condition correlates to catalytic hydrogenation. The substrate in the given reaction has two sites for catalytic hydrogenation, one C=C bond and another the aldehyde group.

Aldehydes and alkenes have similar reactivity toward catalytic hydrogenation, but the aldehyde group in the above substrate is less sterically hindered; thus H2 molecule will add over the aldehyde group and convert it to aldehyde.

Therefore, the product of the given reaction is

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second), Chapter 19, Problem 19.54P , additional homework tip  18

Conclusion

The product of the given reaction is predicted using the given reaction conditions.

Interpretation Introduction

(g)

Interpretation:

The product of the given reaction is to be predicted, considering one molar equivalent of H2 reacts.

Concept introduction:

The C=C functional group of an alkene or the CC functional group of an alkyne can be removed via catalytic hydrogenation. Catalytic hydrogenation is a reaction in which H2 adds to a molecule in the presence of a metal catalyst such as Pt, Pd, or Ni. Catalytic hydrogenation readily reduces an alkene or an alkyne to an alkane. The reduction of an alkyne to an alkene via catalytic hydrogenation favors production of the cis isomer over the trans. Catalytic hydrogenation using a poisoned catalyst (a Lindlar catalyst) reduces an alkyne to a cis alkene.

Expert Solution
Check Mark

Answer to Problem 19.54P

The product of the given reaction is

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second), Chapter 19, Problem 19.54P , additional homework tip  19

Explanation of Solution

The given reaction is

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second), Chapter 19, Problem 19.54P , additional homework tip  20

The given reaction condition correlates to catalytic hydrogenation. The substrate in the given reaction has two sites for catalytic hydrogenation, one CC bond and another the amide group.

The functional groups in alkenes, alkynes, and aldehydes can be selectively reduced over those in ketones, nitriles, and amides. Thus, the H2 molecule is added over the CC triple bond. Catalytic hydrogenation using a poisoned catalyst (a Lindlar catalyst) reduces an alkyne to a cis alkene, but the reaction condition favors one more step as H2 is present in excess. Hence one more mol of H2 molecule is added over C=C double bond and converts it to C-C single bond.

Therefore, the product of the given reaction is

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second), Chapter 19, Problem 19.54P , additional homework tip  21

Conclusion

The product of the given reaction is predicted using the given reaction conditions.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Chapter 19 Solutions

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)

Ch. 19 - Prob. 19.11PCh. 19 - Prob. 19.12PCh. 19 - Prob. 19.13PCh. 19 - Prob. 19.14PCh. 19 - Prob. 19.15PCh. 19 - Prob. 19.16PCh. 19 - Prob. 19.17PCh. 19 - Prob. 19.18PCh. 19 - Prob. 19.19PCh. 19 - Prob. 19.20PCh. 19 - Prob. 19.21PCh. 19 - Prob. 19.22PCh. 19 - Prob. 19.23PCh. 19 - Prob. 19.24PCh. 19 - Prob. 19.25PCh. 19 - Prob. 19.26PCh. 19 - Prob. 19.27PCh. 19 - Prob. 19.28PCh. 19 - Prob. 19.29PCh. 19 - Prob. 19.30PCh. 19 - Prob. 19.31PCh. 19 - Prob. 19.32PCh. 19 - Prob. 19.33PCh. 19 - Prob. 19.34PCh. 19 - Prob. 19.35PCh. 19 - Prob. 19.36PCh. 19 - Prob. 19.37PCh. 19 - Prob. 19.38PCh. 19 - Prob. 19.39PCh. 19 - Prob. 19.40PCh. 19 - Prob. 19.41PCh. 19 - Prob. 19.42PCh. 19 - Prob. 19.43PCh. 19 - Prob. 19.44PCh. 19 - Prob. 19.45PCh. 19 - Prob. 19.46PCh. 19 - Prob. 19.47PCh. 19 - Prob. 19.48PCh. 19 - Prob. 19.49PCh. 19 - Prob. 19.50PCh. 19 - Prob. 19.51PCh. 19 - Prob. 19.52PCh. 19 - Prob. 19.53PCh. 19 - Prob. 19.54PCh. 19 - Prob. 19.55PCh. 19 - Prob. 19.56PCh. 19 - Prob. 19.57PCh. 19 - Prob. 19.58PCh. 19 - Prob. 19.59PCh. 19 - Prob. 19.60PCh. 19 - Prob. 19.61PCh. 19 - Prob. 19.62PCh. 19 - Prob. 19.63PCh. 19 - Prob. 19.64PCh. 19 - Prob. 19.65PCh. 19 - Prob. 19.66PCh. 19 - Prob. 19.67PCh. 19 - Prob. 19.68PCh. 19 - Prob. 19.69PCh. 19 - Prob. 19.70PCh. 19 - Prob. 19.71PCh. 19 - Prob. 19.72PCh. 19 - Prob. 19.73PCh. 19 - Prob. 19.74PCh. 19 - Prob. 19.75PCh. 19 - Prob. 19.76PCh. 19 - Prob. 19.77PCh. 19 - Prob. 19.78PCh. 19 - Prob. 19.79PCh. 19 - Prob. 19.1YTCh. 19 - Prob. 19.2YTCh. 19 - Prob. 19.3YTCh. 19 - Prob. 19.4YTCh. 19 - Prob. 19.5YTCh. 19 - Prob. 19.6YTCh. 19 - Prob. 19.7YTCh. 19 - Prob. 19.8YTCh. 19 - Prob. 19.9YTCh. 19 - Prob. 19.10YT
Knowledge Booster
Background pattern image
Recommended textbooks for you
Text book image
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Text book image
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Text book image
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Text book image
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Text book image
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY