Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 16, Problem 57P
Rank the aryl halides in each group in order of increasing reactivity in nucleophilic
a. chlorobenzene, p-fluoronitrobenzene, m-fluoronitrobenzene
b.
c.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Which of the following is expected to be the MOST reactive towards electrophilic aromatic substitution?
a. p-Cresol
b. p-Toluidine
c. p-Chlorophenol
d.p-Chloroaniline
2. Which of the following is expected to be the LEAST reactive towards electrophilic aromatic substitution?
a. p-Hydroxybenzoic acid
b. p-Methoxybenzoic acid
c. p-Aminophenyl acetate
d. p-Methoxyphenyl acetate
d.
12. What is the simplest fused aromatic hydrocarbon?
a. Naphthalene
b. 1,2-Benzylpyrene
c. Methylbenzene
d. Cyclobenzene
13. In electrophilic aromatic substitution reactions, a phenyl substituent on the
aromatic ring is
a. a deactivator and a m-director
b. a deactivator and an o,p-director
c. an activator and an o,p-director
d. none of the above
14. Acetylide ion formation requires a strong base like NaNH2 which in turn is made
using ammonia and Na. The catalyst used in this reaction is
a. Cu
b. Fe
C. Pt
d. Pd
15. Hydroboration-Oxidation of terminal alkyne results in the formation of an
a. Aldehyde by Markovnikov mechanism
b. Ketone by anti-Markovnikov mechanism
c. Enol by Markovnikov mechanism
d. Aldehyde by anti-Markovnikov mechanism
16.p-Methoxybenzaldehyde can be prepared from anisole using the Gatterman-
Koch formylation. What mixture of reagents is necessary for this process?
a. CO, HCI, AICI3, CuCI
b. CO, SO3, H2SO4
CO2, HCI, AICI3
d. CO2, SO3, H2SO4
e. CO2, HNO3, H2SO4
C.
What is the first step in the general mechanism for electrophilic aromatic substitution?
a. aromatic ring protonation
b.loss of the electrophilic aromatic ring
c. deprotonation of the aromatic ring
d.addition of the electrophilic to the aromatic ring.
Chapter 16 Solutions
Organic Chemistry (6th Edition)
Ch. 16.1 - Prob. 1PCh. 16.2 - Prob. 2PCh. 16.3 - Prob. 3PCh. 16.4 - Prob. 4PCh. 16.5 - Prob. 5PCh. 16.5 - Prob. 6PCh. 16.5 - Prob. 9PCh. 16.5 - Problem 18.9 Draw the product of each reaction
a....Ch. 16.5 - Prob. 11PCh. 16.5 - Prob. 12P
Ch. 16.5 - Prob. 13PCh. 16.6 - Prob. 14PCh. 16.6 - Problem 18.14 Draw all resonance structures for...Ch. 16.6 - Problem 18.15 Classify each substituent as...Ch. 16.7 - Prob. 17PCh. 16.9 - Prob. 22PCh. 16.10 - Problem 18.20 Draw the products of each...Ch. 16.10 - Prob. 24PCh. 16.11 - Problem 18.22 Draw the products formed when each...Ch. 16.12 - Problem 18.23 Devise a synthesis of each compound...Ch. 16.13 - Problem 18.24 Draw the products of each...Ch. 16.13 - Problem 18.25 Draw a stepwise mechanism for the...Ch. 16.13 - Problem 18.26 Draw the products of each...Ch. 16.13 - Prob. 30PCh. 16 - Prob. 37PCh. 16 - 18.35 What is the major product formed by an...Ch. 16 - 18.36 Draw the products formed when phenol is...Ch. 16 - Problem 18.37 Draw the products formed when each...Ch. 16 - 18.38 Draw the products of each reaction.
a. d....Ch. 16 - 18.39 What products are formed when benzene is...Ch. 16 - Prob. 49PCh. 16 - 18.47 For each of the following substituted...Ch. 16 - 18.48 Consider the tetracyclic aromatic compound...Ch. 16 - 18.49 For each N-substituted benzene, predict...Ch. 16 - Prob. 54PCh. 16 - 18.51 Using resonance structures, explain why a...Ch. 16 - Prob. 56PCh. 16 - 18.53 Rank the aryl halides in each group in order...Ch. 16 - Prob. 64PCh. 16 - Prob. 65PCh. 16 - Prob. 66PCh. 16 - 18.63 Synthesize each compound from benzene and...Ch. 16 - Problem 18.64 Synthesize each compound from...
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
- 1. Which is the strongest base? NH2 „NH2 NH2 `NH2 b. O,N C. d. а. 2. Which of the following compounds is the least reactive towards a nucleophilic addition reaction? a. 3-Methyl-2-butanone b. 2,4-Dimethylpentan-3-one C. Acetone d. Methanalarrow_forwardNB: All bonds to benzene must be made using Electrophilic Aromatic Substitution (including Friedel-Crafts reactions) or Nucleophilic Aromatic Substitution! Design a synthesis of each of the following target molecules, starting with benzene: a. pentylbenzene b. 2-chloro-1-propyl benzene d. 3-chloro-1-propyl benzene d. 1-phenyl-1-butanolarrow_forwardWhat would be the effect on the rate of reaction if the concentration of the nucleophile weredoubled in an…a. SN1 reaction? Briefly explain.b. SN2 reaction? Briefly explain.arrow_forward
- Which of the following molecules is anti-aromatic? A. Cyclopentadienyl cation B. cycloheptatriene C. silopentadiene D. cycloheptatrienyl cation E. cyclopentadienyl anionarrow_forwardDrug name: p-cresolarrow_forwardMCQ 16: In SN2 mechanism 'S' stands for A. subordinate B. substitution C. sub-reaction D. systemic reactionarrow_forward
- Which of the following compounds would be most reactive with water acting as a nucleophile or base? Select one: O a. 4-bromo-1-pentene O b. 3-bromo-1-pentene Oc. 5-bromo-1-pentene O d. 2-bromo-1-pentene Arrange the compounds below in order of DECREASING reactivity toward ring nitration. Bromobenzene Nitrobenzene Benzene Toluenearrow_forwardWhich of the following compounds has an activating group? A. Bromobenzene B. Benzoic acid OC. None in the answer OD. Diphenylamine ESTION 2 Which of the following compounds has a deactivating group attached to the benzene ring? OA. Phenol OB. Acetanilide OC. Salicyclic Acid OD. Toluenearrow_forwardWhich of the following reagents will not undergo a substitution reaction with the benzenediazonium chloride salt.arrow_forward
- QUESTION 2 The preparation of a Wittig salt from an alky halide and triphenylphosphine proceeds by a(n) O A. E2 O B. Sn2 OC. E1 O D. free radical O E. Sn1 mechanism. QUESTION 3 Which resonance structure is more reactive as a nucleophile? Ph Ph O A. 1 O B. 2 OC. both are equally reactive Click Save and Submit to save and submit. Click Save All Answers to save all answers. o search F10 F1 F2 F3 F4 F5 F6 23 2 3 4. 7 8 W Y UIarrow_forwardNeed help!arrow_forwardRank the species in each group in order of increasing nucleophilicity. a. CH,, "OH, "NH2 b. H20, OH, "SH in CH3OH c. CH,CH2S", CH;CH2O¯, CH;COO" in CH3OH d. CH3NH2, CH3SH, CH;OH in acetone e. "OH, F", CI" in acetone f. HS, F", CI in CH3OHarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage Learning
ChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill Education
Principles of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill Education
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY
Coenzymes and cofactors; Author: CH15 SWAYAM Prabha IIT Madras;https://www.youtube.com/watch?v=bubY2Nm7hVM;License: Standard YouTube License, CC-BY
Aromaticity and Huckel's Rule; Author: Professor Dave Explains;https://www.youtube.com/watch?v=7-BguH4_WBQ;License: Standard Youtube License