Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 19, Problem 52P
Draw the product(s) of each of the following reactions:
a. benzoic acid + HNO3/H2SO4
b. isopropyltenzene + Cl2 + FeCl3
c. p-xylene + acetyl chloride + AlCl3 followed by H2O
d. o-methylaniline + benzenediazonium chloride
e. cyclohexyl phenyl ether + Br2
f. phenol + H2SO4 + Δ
g. ethylbenzene + Br2/FeBr3
h. m-xylne + Na2Cr2O7 + HCl + Δ
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
What product is obtained from the reaction of excess benzene with each of the following reagents?
a. isobutyl chloride + AlCl3
b. 1-chloro-2,2-dimethylpropane + AlCl3
c. dichloromethane + AlCl3
Give the products, if any, of each of the following reactions:
a. benzonitrile + methyl chloride + AlCl3 b. phenol + Br2
c. benzoic acid + CH3CH2Cl + AlCl3
d. benzene + 2 CH3Cl + AlCl3
Which of the following starting materials and reagents would be best
to produce 2-hexanol?
a. heptanal and 1. CH3MgBr 2. H3O*
b. pentanal and 1. CH3MgBr, 2. H30*
c. hexanal and 1. CH3MgBr, 2. H30*
d. butanal and 1. CH3CH2MgBr, 2. H3O*
Chapter 19 Solutions
Organic Chemistry
Ch. 19.1 - Draw the structure for each of the following: a....Ch. 19.2 - PROBLEM 2
If electrophilic addition to benzene is...Ch. 19.4 - Why does hydration inactivate FeBr3?Ch. 19.6 - Prob. 5PCh. 19.7 - Prob. 6PCh. 19.8 - What is the major product of a Friedel-Crafts...Ch. 19.10 - Describe two ways to prepare each of the following...Ch. 19.12 - Prob. 9PCh. 19.13 - Name the following:Ch. 19.13 - Prob. 12P
Ch. 19.13 - Prob. 13PCh. 19.13 - Prob. 14PCh. 19.14 - Prob. 15PCh. 19.14 - List the compounds in each set from most reactive...Ch. 19.15 - Prob. 18PCh. 19.15 - What product(s) result from nitration of each of...Ch. 19.15 - Prob. 20PCh. 19.16 - Which acid in each of the following pairs is...Ch. 19.16 - Prob. 23PCh. 19.16 - Prob. 24PCh. 19.18 - Show how the following compounds can be...Ch. 19.18 - Give the products, if any, of each of the...Ch. 19.19 - a. Does a coupling reaction have to be used to...Ch. 19.19 - PROBLEM 28
Show how each of the following...Ch. 19.20 - What is the major product(s) of each of the...Ch. 19.20 - Prob. 30PCh. 19.21 - Why isn't FeBr3 used as a catalyst in the first...Ch. 19.21 - Prob. 33PCh. 19.21 - Write the sequence of steps required for the...Ch. 19.21 - Prob. 35PCh. 19.22 - What product is formed from reaction of...Ch. 19.22 - Prob. 37PCh. 19.22 - Draw the structure of the activated ring and the...Ch. 19.23 - Prob. 39PCh. 19.23 - Prob. 40PCh. 19.23 - Diazomethane can be used to convert a carboxylic...Ch. 19.24 - Prob. 42PCh. 19.24 - Prob. 43PCh. 19.24 - Prob. 44PCh. 19.25 - Prob. 45PCh. 19 - Draw the structure for each of the following: a....Ch. 19 - Prob. 47PCh. 19 - Prob. 48PCh. 19 - Prob. 49PCh. 19 - For each of the statements in Column I, choose a...Ch. 19 - What product is obtained from the reaction of...Ch. 19 - Draw the product(s) of each of the following...Ch. 19 - Rank the following substituted anilines from most...Ch. 19 - Prob. 54PCh. 19 - The compound with the 1H NMR spectrum shown below...Ch. 19 - Prob. 56PCh. 19 - Show how the following compounds can be...Ch. 19 - Prob. 58PCh. 19 - Rank each group of compounds from most reactive to...Ch. 19 - Prob. 60PCh. 19 - Describe two ways to prepare anisole from benzene.Ch. 19 - For each of the following components, indicate the...Ch. 19 - Prob. 63PCh. 19 - Prob. 64PCh. 19 - Prob. 65PCh. 19 - Prob. 66PCh. 19 - An aromatic hydrocarbon with a molecular formula...Ch. 19 - The following tertiary alkyl bromides undergo an...Ch. 19 - Show how the following compounds can be...Ch. 19 - Use the four compounds shown below to answer the...Ch. 19 - a. Rank the following esters from most reactive to...Ch. 19 - A mixture of 0.10 mol benzene and 0.10 mol...Ch. 19 - Prob. 73PCh. 19 - Benzene underwent a Friedel-Crafts acylation...Ch. 19 - Prob. 75PCh. 19 - Prob. 76PCh. 19 - Prob. 77PCh. 19 - Friedel-Crafts alkylations can be carried out with...Ch. 19 - Show how the following compounds can be prepared...Ch. 19 - Prob. 80PCh. 19 - Prob. 81PCh. 19 - a. Describe four ways the following reaction can...Ch. 19 - Propose a mechanism for each of the following...Ch. 19 - Prob. 84PCh. 19 - Describe how naphthalene can he prepared from the...Ch. 19 - Prob. 86PCh. 19 - Using resonance contributors for the carbocation...Ch. 19 - Prob. 88PCh. 19 - When heated with chromic acid, compound A forms...Ch. 19 - Prob. 90PCh. 19 - Prob. 91PCh. 19 - What reagents are required to carry out the...Ch. 19 - Show how the following compounds can be prepared...Ch. 19 - An unknown compound reacts with ethyl chloride and...Ch. 19 - How can you distinguish the following compounds...Ch. 19 - P-Fluoronitrobenzene is more reactive toward...Ch. 19 - a. Explain why the following reaction leads to the...Ch. 19 - Describe how mescaline can be synthesized from...Ch. 19 - Propose a mechanism for the following reaction...Ch. 19 - Explain why hydroxide ion catalyzes the reaction...Ch. 19 - Propose a mechanism for each of the following...Ch. 19 - Prob. 102PCh. 19 - Prob. 103PCh. 19 - Describe how 3-methyl-1-phenyl-3-pentanol can he...Ch. 19 - a. How can aspirin be synthesized from benzene? b....Ch. 19 - Prob. 106PCh. 19 - Show how Novocain, a painkiller used frequently by...Ch. 19 - Prob. 108PCh. 19 - Saccharin, an artificial sweetener, is about 300...
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
- Match the ff reagents: a. Br₂ in CH₂Cl₂ b.CrO₃ , H₂SO₄, acetone c. concentrated HCl with ZnCl₂ d. aqueous FeCl₃ e. aqueous NaHCO₃ f. ammoniacal AgNO₃ 1. 4-bromophenol from benzene 2. hexane from 1-hexene 3. 1-hexanol from hexanal 4. hexane from hexanoic acid 5. 2-hexanol from 2-methyl-2-hexanol 6. 1-hexene from 1-hexynearrow_forwardHow would you prepare the following compounds from 2- phenylethanol? More than one step may be required. a. Styrene (PhCH=CH2) b. Phenylacetaldehyde (PhCH2CHO) c. Phenylacetic acid (PhCH2CO2H) d. Benzoic acid e. Ethylbenzene f. Benzaldehyde g. 1-Phenylethanol h. 1-Bromo-2-phenylethanearrow_forwardWhat type of compound will be formed as the major product of the reaction below? H+ H. 2 CH3OH Select one: a. Acetal b. Hemiacetal c. Hemiketal d. Hydrazone e. Ketal f. Oxime g. Imine h. Hydratearrow_forward
- Given the following reagents: a. Br₂ in CH₂Cl₂ b.CrO₃ , H₂SO₄, acetone c. concentrated HCl with ZnCl₂ d. aqueous FeCl₃ e. aqueous NaHCO₃ f. ammoniacal AgNO₃ which will match and quickly differentiate the compounds in the ff: 1. 4-bromophenol from benzene 2. hexane from 1-hexene 3. 1-hexanol from hexanal 4. hexane from hexanoic acid 5. 2-hexanol from 2-methyl-2-hexanol 6. 1-hexene from 1-hexynearrow_forwardWhat is the major product(s) of each of the following reactions? a. bromination of p-methylbenzoic acid b. chlorination of o-benzenedicarboxylic acid c. bromination of p-chlorobenzoic acid d. nitration of p-fluoroanisole e. nitration of p-methoxybenzaldehyde f. nitration of p-tert-butylmethylbenzenearrow_forwardSpecify the reagent you would use in each step of the following synthesis: step 1 step 2 CI Reagents Available a. LIAIH4 f. PBr3 k. CH3CH,MgBr b. H2SO4 g. Dess-Martin periodinane (DMP) I. CoHsMgBr (phenylmagnesium bromide) c. HCI h. NaH m. (CH3)2CHMgBr d. HBr i. NaOH n. Cro3 e. SOCI, J. CH3M9B Write the letters of the reagents in the boxes below. Reagent for step 1 Reagent for step 2arrow_forward
- 12. Which reagents/conditions would lead to the transformation depicted below in high yield? a. NaOMe, MeOH b. MeOH, H₂O* c. NaOEt, EtOH 13. In the structure of 2-fluoropropanoic acid shown, the oxidation number on C1 is the oxidation number on C2 is a. +1, +2, -3 b. -3, +1, +3 d. NaOH, H₂O e. two of these , and the oxidation number on C3 is, c. 0, 0, 0 d. +3,0,-3 e. +2,0, -2 ??? OH 14. What will be the outcome of the following reaction sequence? B. 1. NaOEt, EtOH 2. PCC 3. isopropylMgBr 4. H₂0¹ ??? a. 2-ethyl-3-isopropyl-2,3-dimethyloxirane b. 2,3,4-trimethyl-3,4-epoxyhexane c. 1,2,3,4-tetramethyl-2,3-epoxypentane d. Both a and b are suitable. e. All of the above are correct. OH 15. What is a suitable IUPAC name for the structure shown at the right? OH D. F H OH LOH CH3 3 OHarrow_forwardChoose the best reagents to complete the following reaction. Br2 A excess Br2, NaOH B 0 CH3CO2H D OH 1. Br2 (1 equiv), PC13 (1 equiv) 2. H₂O Br2 CH3CO2H excess Br2arrow_forwardSpecify the reagent you would use in each step of the following synthesis: OH step 1 step 2 Reagents Available a. LIAIH4 f. PBr3 k. CH;CH,MgBr b. H2SO4 g. pyridinium chlorochromate (PCC) I. CęH5MgBr (phenylmagnesium bromide) c. HCI h. NaH m. (CH3)2CHMgBr d. HBr i. NaOH n. Cro3 e. SOCI2 j. CH3M9B Write the letters of the reagents in the boxes below. Reagent for step 1 Reagent for step 2arrow_forward
- Choose the best reagents to complete the reaction shown below. 1118 1. PhMgBr 2. H3O+ OH "Br a (P) A B C D E conc. HBr 1. LiAlH4 2. H3O* 1. H3O+ 2. NaBH4 1. PhLi 2. H3O+ 1. PhMgBr 2. H3O+arrow_forwardFrom the table of available reagents select the one(s) you would use to convert 1-phenylethanol to l-phenylethanethiol Use the minimum number of steps; in no case are more than four steps necessary. List reagents by letter in the order that they are used; example: fa. Reagents available .CO3H a. CH3B. e. H30* i. b. HCI f. NaH c. Hg(OCOCF3)2, (CH3)2C=CH2; then NABH4 g. PBR3 h. POCI3, pyridine j. (CH3)3COH d. (H2N)2C=S; then "OH, H2Oarrow_forwardSpecify the reagent you would use in each step of the following synthesis: a. LiAlH4 b. H₂SO4 c. HCI d. HBr e. SOCI2 H step 1 step 2 Reagents Available CH3 f. PBr3 k. CH3CH₂MgBr g. Dess-Martin periodinane (DMP) 1. C6H5MgBr h. NaH i. NaOH j. CH3MgBr (phenylmagnesium bromide) m. (CH3)2CHMgBr n. CrO3 Write the letters of the reagents in the boxes below. Reagent for step 1 Reagent for step 2arrow_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 LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples 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 EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary 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