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.
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Chapter 16 Solutions
Organic Chemistry
- Illustrate the resonance effect of the methoxy group -OCH3, on the structure of the benzene ring. Draw all the oissuvke resonance forms of methoxybenzene, including the hybrid Based on the structures, explain how the presence of the -OCH3 group affects: (i) the reactivity of the benzene ring towards electrophilic attack (ii) the orientation or point of attack of an incoming electrophilic reagent on the benzene ring.arrow_forwardRank the compounds in each group in order of increasing reactivity in electrophilic aromatic substitution: (a) C6H6, C6H5Cl, C6H5CHO, C6H5OCH3; (b) C6H5CH3, C6H5NH2, C6H5CH2NH2, C6H5CONH2.arrow_forward11. 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_forward
- Rank the compounds in each group according to their reactivity towardelectrophilic substitution.(a) Chlorobenzene, o-dichlorobenzene, benzene(b) p-Bromonitrobenzene , nitrobenzene, phenol(c) Fluorobenzene, benzaldehyde, a-xylene(d) Benzonitrile, p-methylbenzonitr ile,p-methoxybenzonitrilearrow_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
- Show how you would synthesize the following compounds, starting with benzene or toluene and any necessary acyclic reagents. Assume para is the major product (and separable from ortho) in ortho, para mixtures.(a) ethoxybenzene (b) 1,2-dichloro-4-nitrobenzene (c) 1-phenylpropan-2-olarrow_forwardWithin 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_forwardIn an aqueous solution containing sodium bicarbonate, aniline reacts quickly withbromine to give 2,4,6-tribromoaniline. Nitration of aniline requires very strong conditions,however, and the yields (mostly m-nitroaniline) are poor.(a) What conditions are used for nitration, and what form of aniline is present under theseconditions?arrow_forward
- Classify 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_forwardHow will you synthesize cyclohexanecarboxaldehyde (cyclohexylmethanal) from the following reagents? (There are no restrictions on the reagents or the number of steps). (a) Cyclohexanone (b) Ethynylcyclohexane (c) Methyl cyclohexylformate (Remember: Formic acid is the IUPAC recognized name for Methanoic acid) (d) Cyclohexanecarboxylic acid (Cyclohexylmethanoic acid) (e) Vinylcyclohexanearrow_forwardAcetoxybenzene (PhOC(=O)OCH3) is much less reactive than ethoxybenzene (PhOCH2CH3) in electrophilic aromatic substitution reactions. Suggest an explanation for this result, based on an analysis of the inductive and resonance electronic effects of the two substituents on the stability of theWheland intermediate for para substitution by an electrophile E+arrow_forward