a)
Interpretation:
The flaw in the synthesis given is to be stated.
Concept introduction:
In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while
To state:
The flaw in the synthesis given.
b)
Interpretation:
The flaw in the synthesis given is to be stated.
Concept introduction:
In aromatic electrophilic substitution reactions, halogens are ortho and para directing groups. Friedal-Crafts alkylation is not possible with
To state:
The flaw in the synthesis given.
c)
Interpretation:
The flaw in the synthesis given is to be stated.
Concept introduction:
In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carbonyl group is a meta directing and deactivating group. When treated with H2/Pd the –C=O group gets reduced to –CH2 group and –NO2 gets reduced to –NH2 group.
To state:
The flaw in the synthesis shown.
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Chapter 16 Solutions
Organic Chemistry
- (b) Predict the suitable solvent (H2O or CH3COCH3) to increase the reaction of bromopropane (CH3CH2CH2B1) with sodium hydroxide (NaOH). Two reactions are shown below: NaOH, 55 °C CH;CH,CH,Br CH;CH,CH,OH + NaBr H,O (i) NaOH, 55 °C CH;CH,CH,Br CH;CH,CH,OH NaBr H,C CH (ii)arrow_forwardA recently discovered insect in New Guinea was found to express the protectant pheromone shown (PHEROMONE). How would you synthesize this pheromone, using chemistry we have learned? PHEROMONE 1. 1-heptyne; NaNH2; CH3CH2CH2Br 2. КОН, СНСIЗ 1. 1-heptyne; NaNH2; CH3CH2CH2Br 2. H2; Pd/Caco3 3. КОН, СНСIЗ 1. 1-heptene; NANH2; CH3CH2CH2Br 2. КОН; СНСIЗ 1. 1-heptyne; NaNH2; CH3CH2CH2Br 2. LI/NH3 3. CH2C2; Zn(Cu)arrow_forwardA synthon is a concept in retrosynthetic analysis. It is defined as a structural unit within a molecule which is related to a possible synthetic operation. Example: OH bond breaks here synthesis Br + retrosynthesis NEC Na -NaBr Synthons C-C bond formation synthetic equivalents Br D=00 CN OH || ⒸC=N H₂O, H+ hydrolysis do not exist exist functional group transformation Common synthons: C1 synthons: carbon dioxide, carbon monoxide, cyanide, formaldehyde C2 synthons: acetylene, acetaldehyde C₂H4OH synthon: ethylene oxide OH Carbocation synthons: alkyl halides, carbonyl C Carbanion synthons: Grignard reagents, organolithiums, malonic ester/acetoacetic ester, terminal alkyne Use the synthons listed above, propose how you would synthesis the following molecules:arrow_forward
- Following is the structural formula of the tranquilizer meparfynol (Oblivon). Propose a synthesis for this compound starting with acetylene and a ketone. (Notice the -yn- and -ol in the chemical name of this compound, indicating that it contains alkyne and hydroxyl functional groups.)arrow_forwardPlease don't provide handwriting solutionarrow_forwardStarting with cyclohexane and using any other carbon compounds containing 3 carbons or less, synthesize two of the following compounds. These will be multi-step processes. CH a) H,C b) CH, HO c) HO.arrow_forward
- (c)Show step by step how to synthesize methoxybenzene from benzene.arrow_forward22. Explain why the following compound cannot be converted to a Grignard reagent. How would you resolve this problem?arrow_forwardProvide reagents in the spaces provided for the following transformations. If there are multiple steps 7.) needed, then indicate with a 1./2., etc., as appropriate. In several instances, there is more than one right answer. ОН E Br F G В Br Br K al `Br Br м obtained from fossil fuels in the ground H. A H В K L F M Garrow_forward
- Questão 10A certain hydrocarbon had the molecular formula C16H26 and contained two triple bonds. Ozonolysis resulted in CH3(CH2)4CO2H and HO2CCH2CH2CO2H as the only products. What is the reasonable structure for this hydrocarbon? Hexadec-6,10-dino undec-1,5-dino Hept-1,5-dino hex-1,5-dino naharrow_forward2.arrow_forwardPhineas and Ferbs, two brothers who enjoy vacations, doing fun things every summer. This summer the brothers and their friends carry out an organic synthesis with an unknown compound (L1) that contains 52% Carbon, 6% Hydrogen and 42% bromine, this compound (L1) is treated with magnesium in ether to obtain L2 , which reacts violently with D2O for 1-methyl cyclohexene with a deuterium atom in the methyl group (L3). The L2 reaction is treated with acetone followed by hydrolysis to give L4. Heating L4 with concentrated sulfuric acid gives L5, which decolors the bromine, obtaining L6. L5 undergoes hydrogenation with excess hydrogen and platinum as a catalyst giving rise to isobutyl cyclohexane. Determine the structures of compounds L1 through L6.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning