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Interpretation:
The major products that are formed when each of the given compound reacts with
Concept introduction:
The common types of electrophilic substitution reaction of
When an aromatic compound reacts with
Para substitution is more stable over ortho due to steric hindrance at the ortho position.
Activating groups like alkyl groups gives substitution at the ortho and para position. Because they increase the electron densities at the ortho and para due to the delocalization of pi electrons of benzene ring. Ortho and para sites of the benzene ring is highly electron rich and thus electrophile usually attacks on these sites.
Deactivating group gives substitution at the meta position. Such electron withdrawing group gives stable product at meta position.
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Chapter 15 Solutions
Organic Chemistry, 12e Study Guide/Student Solutions Manual
- How 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 (PHCH2COOH) (d) Benzoic acid (e) Ethylbenzene (f) Benzaldehyde (g) 1 -Phenylethanol (h) l-Bromo-2-phenylethanearrow_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_forwardWhen A is reacted with hot aqueous NaOH, a compound B of molecular formula C8H11NO is produced. With this information, write the correct structure of B and propose the reaction mechanism (step by step, with the correct use of arrows) to obtain B.arrow_forward
- A step in a synthesis of PGE1 (prostaglandin E1, alprostadil) is the reaction of a trisubstituted cyclohexene with bromine to form a bromolactone. Propose a mechanism for formation of this bromolactone and account for the observed stereochemistry of each substituent on the cyclohexane ring. Alprostadil is used as a temporary therapy for infants born with congenital heart defects that restrict pulmonary blood flow. It brings about dilation of the ductus arteriosus, which in turn increases blood flow in the lungs and blood oxygenation.arrow_forwardAmines are converted into alkenes by a two-step process called Hofmann elimination. SN2 reaction of the amine with an excess of CH3I in the first step yields an intermediate that undergoes E2 reaction when treated with silver oxide as base. Pentylamine, for example, yields 1-pentene. Propose a structure for the intermediate, and explain why it readily undergoes elimination.arrow_forward2. How would you prepare the following substances from 2-cyclohexenone? More than one step may be needed. (a) Cyclohexene (b) 3-Phynylcyclohexanone (c) 3-Oxocyclohenanecarboxylic acid (d) Methyleyclohexanearrow_forward
- (c) The structures of lycopene, beta-carotene and retinol are shown below. Lycopene Beta-carotene H3C CH; CH3 CH3 OH Retinol (vitamin A) CH3 Using appropriate reaction mechanisms: (i) Show how lycopene is converted into beta-carotene. (ii) Briefly explain how retinol is formed from beta-carotene.arrow_forward1. At what position and on what ring would you expect the following substances to undergo electrophilic substitution? (b) CH3 Br lel CH3 2. 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, 0-xylene (d) Benzonitrile, p-methylbenzonitrile, p-methoxybenzonitrilearrow_forwardHNO3 H,SO, Predict the product of following reaction : (A) (B) -NO2 NO2 O,N. (A) (B) (C) O (D)arrow_forward
- Propose mechanisms consistent with the following reactions. (a) (b) (c) (d) (f) (breif Written explantion for each PLEASE) Propose mechanisms consistent with the following reactions. (a) HBr ROOR Br H₂SO4 (b) H₂O OH Br HBr Br (d) (c) CHBr Br NaOH Br Br (e) HCI CH3CH₂OH Br OCH2CH3 Br ED-8 CH2CH3 H- OH H+, H₂O (f) H OH CH3CH2 CH2CH3 CH2CH3 (continued)arrow_forward(d) Draw the structures of compounds C and D and identify reagent E in the reaction scheme below. Outline a mechanism for the formation of compound B from compound . Но OH 1. LIAIH, 2. Н,о° 4 H,SO, catalyst A B E F OHarrow_forwardUsing your reaction roadmap as a guide, show how to convert 1-butanol and ethanol into racemic 2-ethoxy-1-butanol. You must use 1-butanol and ethanol as the source of all carbon atoms in the ether product. (2) OH (1) i 2-ethoxy-1-butanol (racemic) (c) ethylene oxide a OH (a) (CH3)3 CO K+, THF (d) H₂SO4, H₂O (b) OsO4, H₂O2 OH 1 Suggest reagents and experimental conditions for each step in this synthesis. From the choices provided, suggest appropriate reagents for each step. More than one reagent may be necessary. Use the minimum number of steps possible. Enter your answer as a letter, or a series of letters, in the order necessary to bring about the steps shown. Reagents: Br OH (e) m-chloroperoxybenzoic acid (mCPBA) (f) pyridinium chlorochromate (PCC) + || (9) H₂SO4 (anhydrous) (j) Na, NH3 (1) (h) NaOH (k) NBS, heat (i) PBr3 (N-bromosuccinimide)arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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