Interpretation:
The
Concept introduction:
Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain a meta directing substituent group are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.
As an exception, the aromatic rings that are either substituted by a strongly electron-withdrawing groups such as carbonyl or basic amino group that can be protonated do not react in Friedal crafts reaction, as they deactivate the ring.
To rank:
The aromatic compounds bromobenzene, toluene, phenol, aniline, nitrobenzene and p-bromotoluene in the expected order of their reactivity towards Friedal-Crafts alkylation. Further to state which of them are unreactive.
Trending nowThis is a popular solution!
Chapter 16 Solutions
Organic Chemistry
- 11. See Fundamentals P167 for Figure 5.6 Use Figure 5.6 to rank the compounds in each of the following groups in order of their reactivity toward electrophilic aromatic substitution: (a) Nitrobenzene, phenol (hydroxybenzene), toluene (b) Phenol, benzene, chlorobenzene, benzoic acid (c) Benzene, bromobenzene, benzaldehyde, aniline (aminobenzene)arrow_forwardRank the compounds in each of the following groups in order of their reactivity to electrophilic substitution: (a) Nitrobenzene, phenol, toluene, benzene (b) Phenol, benzene, chlorobenzene, benzoic acid (c) Benzene, bromobenzene, benzaldehyde, anilinearrow_forward-Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the molecular formula C10H16 and a UV absorption maximum at 232 nm. On hydrogenation with a palladium catalyst, 2,6-dimethyloctane is obtained. Ozonolysis of -ocimene, followed by treatment with zinc and acetic acid, produces the following four fragments: (a) How many double bonds does -ocimene have? (b) Is -ocimene conjugated or nonconjugated? (c) Propose a structure for -ocimene. (d) Write the reactions, showing starting material and products.arrow_forward
- Within each structure, rank the indicated nitrogens by increasing basicity. Explain all (guide line: Increasing basicity. Begin by identifying the classification of the nitrogen.) (b) nicotine cyamemaine, an anti-psychotic drug Pentenyl cation Pentenyl anion (d) HN LY (a) C₂H₂CH-N-C,H, LSD CH₂0. Which of these belong to MO of Vin ,t-pentadienyl? Ponlenyl radical CH₂ H (e) CH-C) HN utabrine (anti-malarial) ipsapirone, an anxiolytic drug 8888 81818 - Which of these belong to HOMO in ,,-heptatrienyl radical? And how many electron/s it has? two e, one e two e, one e, - Construct a qualitative MO diagram for the following systems and discuss how the MOS are modified by addition of the substituent (each ¹ mark) a) CH=CH-CH=CH compared to CH=CH-CHO Acrolein (propenal) NET₂ NHỊCH, b) CH=CH-CN compared to CH=CH-COOH c) CH=CH-F compared to CH=CH-NH - Comparing FMO of the given compounds with each other while doing reaction with a nucleophile and electrophile a) CH=CH-CH=CH, compared to CH=CH-CHO…arrow_forwardClassify the compounds in each of the following sets in decreasing order of their expected reactivity toward nucleophilic acyl substitution and explain your answers. H;C- H;C– H;C- Cl OCH3 `NH, (а) H;C- H;C- H;C– OCH,CH3 OCH,CCI3 DCH(CF3)2 (b)arrow_forwardRank the compounds in each of the following groups in order of their reactiv- ity to electrophilic substitution: (b) Phenol, benzene, chlorobenzene, benzoic acid (c) Benzene, bromobenzene, benzaldehyde, anilinearrow_forward
- Rank the compounds in each group according to their reactivity toward electrophilic substitution: (a) Chlorobenzene, o-dichlorobenzene, benzene (b) p-Bromonitrobenzene, nitrobenzene, phenol (c) Fluorobenzene, benzaldehyde, o-dimethylbenzenearrow_forwardت ا كل وخویه م اکتریار Q6/ Rank the compounds in each group in order of increasing reactivity in electrophilic aromatic substitution. NH NO2 b) O O Darrow_forward2) The Diels-Alder reaction, developed by German chemists Otto Diels and Kurt Alder (who received the Nobel Prize in 1950 for their discovery), has great synthetic importance due to the possibility of forming an unsaturated six-membered cycle without involving intermediates ionic. About the reaction, answer: (a) Indicate the reagents necessary for the synthesis of the following compounds, indicating who is the diene and who is the dienophile.arrow_forward
- Styrene (vinylbenzene) undergoes electrophilic aromatic substitution much faster thanbenzene, and the products are found to be primarily ortho- and para-substituted styrenes.Use resonance forms of the intermediates to explain these results.arrow_forwardv) What products would you expect if 2-butyne were treated with ozone in the presence ofacetic acidvi) What products would you expect if 1-butyne were treated with ozone in the presence ofacetic acidvii) What products would you expect if 2-butyne were treated with KMnO4 in the presenceof KOH in water?viii) What products would you expect if 1-butyne were treated with KMnO4 in the presence of KOH in waterarrow_forward(a) Which is more reactive towards Electrophilic aromatic substitution (EAS)? (b) Which of the following is a a meta-substituted compound? (c) Which is the least reactive towards Electrophilic aromatic substitution (EAS)? (d) Which is an ortho-substituted compound?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning