Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 15, Problem 20P
Suggest appropriate methods for preparing each of the following
Expert Solution & Answer
Interpretation Introduction
Interpretation:
The appropriate method of preparation for each of the given organometallic compounds is to be suggested.
Concept introduction:
The reaction of a metal with an organic halide is an oxidation–reduction in which the metal is the reducing agent.
lithium metal and magnesium metal in the presence of dry ether as a solvent, reacts with alkyl halides to produce the corresponding organo lithium and magnesium compounds respectively.
Organolithium reagents are used to prepare organometallic compounds analogous of terminal alkynes.
Organolithium compounds are strongly basic and react with terminal alkynes by abstracting the acidic proton and forming an alkane.
Answer to Problem 20P
Solution:
Explanation of Solution
Alkyl halides react with lithium metal in the presence of dry ether as a solvent to produce the corresponding organo lithium compound.
The product given is cyclopentyl lithium. Reaction of cyclopentyl bromide with lithium metal in the presence of diethyl ether as a solvent will produce this cyclopentyl lithium.
The reaction is shown below:
The product given is tert-butyl magnesium bromide. Tert-butyl bromide react with magnesium metal in the presence of diethyl ether as a solvent will produce this tert-butyl magnesium bromide.
The reaction is shown below:
Organolithium reagents are used to prepare organometallic compounds analogous of terminal alkynes.
Organolithium compounds are strongly basic and react with terminal alkynes by abstracting the acidic proton and forming an alkane.
Thus, phenyl acetylene reacts with an organo lithium reagent like butyl lithium to produce lithium phenylacetylide and butane.
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!
Students have asked these similar questions
✓ edict the products of this organic reaction:
----
။
A
CH3–C−NH–CH2–C−CH3 + KOH
?
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.
Explanation
Check
Click anywhere to draw the first
atom of your structure.
C
2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessibili
Predict the product of this organic reaction:
A
HO-C-CH3 + CH3NH2
P+ H2O
Specifically, in the drawing area below draw the condensed structure of P.
If there is no reasonable possibility for P, check the No answer box under the drawing area.
Explanation
Check
Click anywhere to draw the first
atom of your structure.
m
H
1) OsO4, pyridine
2) Na2SO3 or
NaHSO3 in H₂O
2 products
Chapter 15 Solutions
Organic Chemistry - Standalone book
Ch. 15.1 - Each of the following organometallic reagents will...Ch. 15.3 - Write equations showing how you could prepare...Ch. 15.4 - Lithium diisopropylamide is often used as a strong...Ch. 15.5 - Write the structure of the organic product of each...Ch. 15.7 - Prob. 5PCh. 15.8 - Prob. 6PCh. 15.9 - Prob. 7PCh. 15.9 - Like nickel, iron reacts with carbon monoxide to...Ch. 15.9 - Prob. 9PCh. 15.9 - What is the oxidation state of manganese in the...
Ch. 15.9 - Prob. 11PCh. 15.10 - Prob. 12PCh. 15.10 - Prob. 13PCh. 15.11 - Give the structure including stereochemistry of...Ch. 15.11 - Prob. 15PCh. 15.12 - Homogeneous catalytic hydrogenation of the...Ch. 15.12 - Prob. 17PCh. 15.13 - What alkenes are formed from 2-pentene by olefin...Ch. 15.13 - The product of the following reaction was isolated...Ch. 15 - Suggest appropriate methods for preparing each of...Ch. 15 - Prob. 21PCh. 15 - Predict the principal organic product of each of...Ch. 15 - Prob. 23PCh. 15 - Predict the principal organic product of each of...Ch. 15 - Prob. 25PCh. 15 - A different stereoisomer of...Ch. 15 - Prob. 27PCh. 15 - Using phenyllithium and any necessary organic or...Ch. 15 - Prob. 29PCh. 15 - A number of drugs are prepared by reactions in...Ch. 15 - The following conversion was carried out in two...Ch. 15 - Outline syntheses of (a)...Ch. 15 - (S)-(+)-Ibuprofen can be prepared by...Ch. 15 - Like other hydroborations, the reaction of alkynes...Ch. 15 - The sex attractant of the female silkworm has been...Ch. 15 - Prob. 36PCh. 15 - (a) Exaltolide, a musk substance, has been...Ch. 15 - Prob. 38PCh. 15 - Prob. 39PCh. 15 - Cyclobutadiene and...Ch. 15 - Cyclobutadiene and (Cyclobutadiene)tricarbonyliron...Ch. 15 - Cyclobutadiene and...Ch. 15 - Cyclobutadiene and...Ch. 15 - Cyclobutadiene and...
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
- ● Biological Macromolecules Naming and drawing cyclic monosaccharides Your answer is incorrect. • Row 1: Your answer is incorrect. Row 3: Your answer is incorrect. • Row 4: Your answer is incorrect. Try again... 0/5 Give the complete common name, including anomer and stereochemistry labels, of the following molecules. You will find helpful information in the ALEKS resource. CH2OH OH OH H H I H OH OH H] H CH2OH H OH ẞ-L-sorbose HOCH2 OH OH H HOCH2 H OH OH H OH H H CH2OH OH H H OH H I- H OH H OH Explanation Recheck W E R % 25 α B Y X & 5 D F G H McGraw Hill LLC. All Rights Reserved. Terms of Use | Pr Parrow_forwardWhat is the missing reactant in this organic reaction? + R -A HO IN + H₂O Specifically, in the drawing area below draw the skeletal ("line") 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. Explanation Check Click and drag to start drawing a structure. © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Centerarrow_forwardStuc X ctclix ALE X A ALE אן A ALEX Lab (195 X Nut x M Inb x NU X NUT X Unt x + → C www-awu.aleks.com/alekscgi/x/Isl.exe/10_u-lgNslkr7j8P3jH-IQ1g8NUi-mObKa_ZLx2twjEhK7mVG6PulJI006NcKTV37JxMpZuyrVCdQolLAKqp_7U3r1GUD3... New Chrome available: Naomi Question 26 of 39 (4 points) | Question Attempt: 1 of Unlimited Give the IUPAC name. 2,3-dimethylhexane Part: 1/2 Part 2 of 2 Draw the skeletal structure of a constitutional isomer of the alkane above that contains a different number of carbons in its longest chain. Skip Part Check Click and drag to start drawing a structure. 3 Finance headline Q Search mwa Harvard Intensifi... X Save For Later 00 dlo HB Submit Assignment 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessibility a 9:11 PM 4/22/2025arrow_forward
- Predict the product of this organic reaction: + NH2 HO A 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. Click and drag to start drawing a structure. ✓arrow_forward个 Stuc X ctclix ALE X A ALE × A ALE X Lab x (195 × Nut x M Inbx EF 目 → C www-awu.aleks.com/alekscgi/x/Isl.exe/10_u-IgNslkr7j8P3jH-IQ1g8NUi-mObKa_ZLx2twjEhK7mVG6PulJI006NcKTV37JxMpz Chapter 12 HW = Question 27 of 39 (5 points) | Question Attempt: 1 of Unlimited Part: 1/2 Part 2 of 2 Give the IUPAC name. Check 3 50°F Clear ©2025 McGraw Hill L Q Search webp a عالياكarrow_forward个 Stuck x ctc xALE X A ALE × A ALE X Lab x (19: x - G www-awu.aleks.com/alekscgi/x/Isl.exe/10_u-lgNslkr7j8P3jH-1Q1g8NUi-mObka ZLx2twjEhK7mVG6PUUIO06 Chapter 12 HW 三 Question 26 of 39 (4 points) 1 Question Attempt: 1 of Unlimited Answer the following questions about the given alkane. Part: 0 / 2 Part 1 of 2 Give the IUPAC name. Skip Part 2 53°F Clear Check × Q Search hp hp 02arrow_forward
- Calculate the equilibrium constant at 25.0 oC for the following equation. Cd(s) + Sn+2(aq) ↔Cd+2(aq) + Sn(s) Group of answer choices 3.11x104 1.95x1018 9.66x108 1.40x109arrow_forwardWhat is the pH at the cathode for the following cell written in line notation at 25.0 oC with a Ecell = -0.2749 V? Ni(s)|Ni+2(aq, 1.00 M)||H+1(aq, ?M)|H2(g, 1.00 atm)|Pt(s)arrow_forwardCalculate Ecell for a hydrogen fuel cell at 95.0 oC using the following half-reactions with PH2 = 25.0 atm and PO2 = 25.0 atm. O2(g) + 4H+1(aq) + 4e-1 → 2H2O(l) Eo = 1.229 V 2H2(g) → 4H+1(aq) + 4e-1 Eo = 0.00 Varrow_forward
- Calculate Ecell at 25.0 oC using the following half-reactions with [Ag+1] = 0.0100 M and [Sn+2] = 0.0200 M. Ag+1(aq) + 1e-1 Ag(s) Sn+2(aq) + 2e-1 Sn(s)arrow_forwardDone 18:19 www-awu.aleks.com Chapter 12 HW Question 27 of 39 (5 points) | Question Attempt: 1 of Unlimited .. LTE סוי 9 ✓ 20 ✓ 21 × 22 23 24 25 26 27 28 29 30 Answer the following questions about the given alkane. Part: 0 / 2 Part 1 of 2 Classify each carbon atom as a 1º, 2º, 3º, or 4°. Highlight in red any 1° carbons, highlight in blue any 2° carbons. highlight in green any 3° carbons, and leave any 4° carbons unhighlighted. Skip Part Check Save For Later © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use Privacy Center | Accessibility ☑ คarrow_forward< Done 19:22 www-awu.aleks.com Chapter 12 HW Question 4 of 39 (2 points) | Question Attempt: 5 of Unlimited : .. LTE סוי 1 ✓ 2 ✓ 3 = 4 ✓ 5 ✓ 6 ✓ 7 ✓ 8 ✓ 9 = 10 11 ✓ 12 Consider the molecule (CH3)2CHCH2CHCн for the following questions. Part 1 of 2 Which of the following molecules is/are constitutional isomer(s) to (CH3)2CHCH2CH2CH3? Check all that apply. Part 2 of 2 (CH3),C(CH2)2CH3 CH3 H,C-CH-CH-CH, CH 3 None of the above. ☑ Which of the following molecules is/are identical molecules to (CH3)2CHCH2CH2CH₁₂? Check all that apply. CH3 H,C-CH-CH₂-CH2-CH, CH3(CH2)2CH(CH3)2 CH2-CH2-CH3 HỌC-CH=CH, 乂 ☑ а None of the above Check Save For Later Submit Assignment © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center Accessibilityarrow_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
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Characteristic Reactions of Benzene and Phenols; Author: Linda Hanson;https://www.youtube.com/watch?v=tjEqEjDd87E;License: Standard YouTube License, CC-BY
An Overview of Aldehydes and Ketones: Crash Course Organic Chemistry #27; Author: Crash Course;https://www.youtube.com/watch?v=-fBPX-4kFlw;License: Standard Youtube License