5. Ignoring double-bond stereochemistry, what products would you expect from elimination reactions of the following alkyl halides? Which product will be the major product in each case? çI CHa CH3CHCH2-C-CHCH3 Br ÇH3 CH3CH2CHCHCH3 (a) (b) ÇH3 (c) Br -CHCH3 ČH3
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- Predict the dehydrohalogenation product(s) that result when the following alkyl halides are heated in alcoholic KOH. When more than one product can be formed, rank them in terms of their predicted stability (1 is most stable isomer, 2 the next most stable isomer, etc...) a) b) HD HD H CH3 ''CI H CH3 Br 'Br KOH EtOH KOH EtOH KOH EtOHPredict the product(s) for each reaction below. In each case, draw the resonance forms of the intermediate to explain the observed regiochemistry. (a) (b) (c) (d) CN CH30. CH3 HNO3 H₂SO4 CH₂ (CH₂CHCI, AIC? Cl₂, FeCl3 ? B. CUCWhich stereoisomer of 3-hexene forms (3S,4S)-4-bromo-3-hexanol and (3R,4R)-4-bromo-3-hexanol when it reacts with Br2 and H2O?
- Draw structural formulas for the isomeric carbocation intermediates formed on treat- ment of each alkene with HCl. Label each carbocation 1°, 2°, or 3° and state which of the isomeric carbocations forms more readily. CH₂CH3 (a) H₂C=C (c) CH3 CH3 (b) (d) H₂C-CH=CH-CH36. Write the IUPAC name for the following compounds. Show the stereochemistry whenever required (a) HO NH2 CI (b) NH2 QH но (c) он Br H. (d) (e) OH Br Br8. Predict the major product(s) for the following reactions. Include the correct stereochemistry in your product structure(s). (a) -6-4- CO₂CH3 to-It- CO₂CH3 (b) OHC. 32- (c) CHO OMe CHO Er + (d)
- H3C N- H₂NNH₂ H⭑ CH3 H3C IN CH3 Hydrazine reacts with 2,4-pentanedione to yield 3,5-dimethylpyrazole. Including protonations and deprotonations, the reaction takes 12 steps. Write out the mechanism on a sheet of paper and then draw the structure of the product of step 6. • You do not have to consider stereochemistry. •You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • In an elimination step, include the structure of the leaving group, but draw it in its own sketcher. Separate structures with + signs from the drop-down menu. ? Sn th Previous NextOrder each set of compounds with respect to SN2 reactivity: (a) CH3 CH3CH2CH2CI CI H3C-C-CI CH3CH2CHCH3 CH3 (b) CH3 CH3 CH3B CH3CHCHCH3 CH3CHCH,Br Br 7. Reaction of HBr with (R)-3-methylhexan-3-ol yields (±)-3-bromo-3-methyl- hexane. Explain. OH CH3CH2CH2CCH2CH3 3-Methylhexan-3-ol CH3 8. Predict the major alkene product from the following eliminations: (a) H3C (b) H3C CH3 CH3CO2H КОН CH3CHCBr Heat CH2CH3 H. Br11. Plan syntheses of the following compounds. You may use the given starting material and any compound containing five or fewer carbons. (a) MeO MeO CN TOXXON anything with five or fewer carbons. CN (b) (c)
- A chemist allows some pure (2S,3R)-3-bromo-2,3-diphenylpentane to react with a solution of sodium ethoxide(NaOCH2 CH3) in ethanol. The products are two alkenes: A (cis-trans mixture) and B, a single pure isomer. Under the same conditions, the reaction of (2S,3S)-3-bromo-2,3-diphenylpentane gives two alkenes, A (cis-trans mixture) and C. Upon catalytic hydrogenation, all three of these alkenes (A, B, and C) give 2,3-diphenylpentane. Determine the structures of A, B, and C; give equations for their formation; and explain the stereospecificity of these reactions.7. Predict the major product(s) of the following reactions: (a) (c) CI CO₂H CH3CH₂CI AICI 3 HNO3 H₂SO4 ? (b) (d) N(CH₂CH3)2 CH3CH₂COCI AICI3 SO3 H₂SO4 ? ?2. Show the structures of the carbocation intermediates you would expect in the following reactions: CH3 CH3 CH3CH2C=CHCHCH3 (a) (b) -CHCH3 HI ? HBr ? 3. What product would you expect to obtain from addition of Br2 to 1,2-dimethyl- cyclohexene? Show the cis or trans stereochemistry of the product.