Kumada Coupling: m-Diisobutylbenzene below could hypothetically be synthesized by Friedel-Crafts reaction. Write out the reaction with a mechanism and give two reasons why you would NOT get the desired product. NOT YO
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- Treatment of 1,3,6-cyclononatriene (Compound 1), or its dimethyl derivative (Compound 2), with potassium amide (KNH₂) in liquid ammonia results in the formation of anion 1a or 2a, respectively (J. Am. Chem. Soc. 1973, 95, 3437-3438): 9 15.85a 2 6 3 4 5 Compound 1 (R=H) Compound 2 (R=CH3) * You answer is incorrect. KNH₂ KNH₂ 1a (anion) 2a (anion) Of the following, which is NOT one of the four resonance structures of 1a?Gamma(y)-amino butyric acid (GABA) is a neurotransmitter (a chemical that is used to send signals from one neuron to another) of the mammalian central nervous system. In order to understand how GABA works, conformationally restricted analogues, such as compound 1, have been made. During a synthesis of compound 1, compound 2 was subjected to allylic bromination using NBS and a radical initiator (AIBN) instead of light (Aust. J. Chem. 1981, 34, 2231-2236). H₂N. CH3 GABA CO₂H CH3 dddd CH3 H₂N Modify the structures given below to draw all eight possible allylic bromides that can be formed when compound 2 undergoes allylic bromination, considering all possible regiochemical and stereochemical outcomes. You can use the single bond tool to add/remove pi bonds. CH3 CO₂H CH3 solddd CH3 CH3 2 CH₂ CO₂EtAcid Catalyzed Aromatization of Carvone: 1. Starting with the ketone, below, draw a mechanism for the reaction to give the phenol as shown. H2SO4 HO- H₂O 2. Why do we use CDCl instead of CHCl, for acquiring our NMR spectra? 3. Why does it not matter which enantiomer of carvone is used for this reaction? What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?
- Q1/ Predict the major product(s) you would expect to obtain from sulfonation of the follow substances: (a) o-Chlorotoluene (b) m-Bromophenol (c) p-Nitrotoluene Q2/ Show the steps involved in the Friedel-Crafts reaction of benzene with CH3CI.(1) (11) (111) (b)Give products and mechanisms for the following reactions. OH CH₂SO над сам _N_N_ но HO BShow how you would use the Friedel–Crafts acylation, Clemmensen reduction, and/or Gatterman–Koch synthesis to prepare the following compounds:(a) p-methoxybenzaldehyde (b) 3-methyl-1-phenylbutane(c) 1-phenyl-2,2-dimethylpropane (d) n-butylbenzene
- explain some of the hazards (name at least three) involved in the Friedel-Crafts Acylation: Synthesis of 4-methoxyacetophenone from anisole experiment. What are some necessary safety precautions when working with aluminum chloride? List compounds that react in a hazardous manner with aluminum chloride and are therefore incompatible. What hazardous by-products are formed in this experiment? Why is it necessary to perform this experiment in the fume hood?(a) Describe the following giving chemical equations :(i) De-carboxylation reaction (ii) Friedel-Crafts reaction(b) How will you bring about the following conversions?(i) Benzoic acid to Benzaldehyde (ii) Benzene to m-Nitroacetophenone (iii) Ethanol to 3-Hydroxybutanal(d) Ozonolysis of 3,4-dimethyl-3-hexene gives compound D. (i) Write the reaction step for the formation of D by including the appropriate reagents. (ii) The mass spectrum of compound D shows a fragment ion peak at m/z 57. Propose the structure of this fragment ion. (ii) Identify the more stable resonance of the proposed structure in (ii).
- 3) While we expect to get one major product, this reaction could potentially have some issues with formation of multiple products. What is the relationship between the two major products that you might expect for the reaction of E-stilbene and dimethyl fumarate? Why will this not matter when you look at the NMR? 4) In addition to the issue raised in prelab Q3, 2,3-dihydrofuran and styrene will also give give two additional major products - what is their relationship, and will this matter when you look at the NMR?(b) The 1H-NMR spectrum of compound B, C5 H10 O2, consists of the following signals: 8 1.2 (d, 6H), 2.0 (s, 3H), and 5 (septet, 1H); contains an ester. Draw the structural formula of compound B. • You do not have to consider stereochemistry. • Explicitly draw all H atoms. ୫) C n ? ChemDoodle ® Show Hintb) Optical isomers can often be formed during these reactions. For products A-H indicate how many different optical isomers you expect to form for each from these reactions (you do not have to indicate whether they are diastereomers/enantiomers). c) In the preparation of substance D by ozonolysis, the second step is necessary treatment of the reaction mixture with zinc in acetic acid. If we forgot this step, we would get substance V instead of substance D, which would probably explode when isolated. What is the structure of substance V? *24 X 1: ozone V e) What products do you expect to form if they react with alkene X: I - HBr in diethyl ether; II - Brl in methanol; III - PhSCI in diethyl ether; IV - Selectfluor in methanol. P M EtOH NA EtONa PhSNa EtOH E H+ O TsCl Pyridín F- T2, Pd/C G4 mCPBA H₂SO4 10 %, H₂O 1: BH3 H◄ 2: H₂O₂ ill X Br₂ cyclohexane HCI A > В B HBr warmth, benzoylperoxid 1: ozone 2: Zn, ACOH Mg THF с D D₂O K I + J NaOH
