Concept explainers
(a)
Interpretation:
The stereoisomeric products of (3S, 4S)-3-bromo-4-methylhexane in
Concept Introduction:
Primary
Secondary alkyl halide undergoes
(b)
Interpretation:
The stereoisomeric products of (3S, 4R)-3-bromo-4-methylhexane in
Concept Introduction:
Primary alkyl halide undergoes
Secondary alkyl halide undergoes
(c)
Interpretation:
The stereoisomeric products of (3R, 4R)-3-bromo-4-methylhexane in
Concept Introduction:
Primary alkyl halide undergoes
Secondary alkyl halide undergoes
(d)
Interpretation:
The stereoisomeric products of (3R, 4S)-3-bromo-4-methylhexane in
Concept Introduction:
Primary alkyl halide undergoes
Secondary alkyl halide undergoes
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Organic Chemistry (8th Edition)
- Draw the products of each of the following SN2/E2 reactions. If the products can exist as stereoisomers, show which stereoisomers are formed. a.(3S,4S)-3-bromo-4-methylhexane + CH3O- b. (3R,4R)-3-bromo-4-methylhexane + CH3O- c. (3S,4R)-bromo-4-methylhexane + CH3O- d. (3R,4S)-3-bromo-4-methylhexane + CH3O-arrow_forwardTreatment of alkenes A and B with HBr gives the same alkyl halide C. Draw a mechanism for each reaction, including all reasonable resonance structures for any intermediate. Br -CHCH2CH, HBr HBr -CH=CHCH, -CH2CH=CH2 A B.arrow_forwardDraw the major product(s) of the reaction of 1-methylcyclohexene with the following reagents, disregarding stereoisomers: 1. NBS/∆/peroxide 2 . Br2/CH2Cl2 3. HBr 4. HBr/peroxideb. For each reaction, show which stereoisomers are obtained.arrow_forward
- Order the following compounds with respect to SN1 reactivity: Br CH2BR CH CH3 CBr 3. Assuming that the nitrogen in enamine is sp? hybridized, explain why the double bond of an enamine is more nucleophilic than a typical alkene double bond. Propose the mechanism for the reaction below and use resonance structure to explain why the other regioisomer does not form. Br HBr OCH3 OCH3arrow_forwardDraw the substitution products for each of the following SN2 reactions. If the productscan exist as stereoisomers, show which stereoisomers are formed:a. (3S,4S)@3@bromo@4@methylhexane + CH3O- b. (3S,4R)@3@bromo@4@methylhexane + CH3O- c. (3R,4R)@3@bromo@4@methylhexane + CH3O- d. (3R,4S)@3@bromo@4@methylhexane + CH3O-arrow_forwarda. Draw the major product(s) of the reaction of 1-methylcyclohexene with the following reagents, disregarding stereoisomers: 1. NBS/Δ/peroxide 2. Br2/CH2Cl2 3. HBr 4. HBr/peroxide b. For each reaction, show which stereoisomers are obtained.arrow_forward
- Propose a reasonable synthetic route for the following reaction: II CH,CH,-C-CI Zn(Hg) (1)? (2)? AICI, HCI (3)? СООН HNO3 (4)? H,SO,arrow_forwardGive the substitution and elimination products for the following reactions, showing the configuration of each product: CH30- SN2/E2 conditions a. (S)-2-chlorohexane b. (S)-2-chlorohexane CH3OH SN1/E1 conditions c. trans-1-chloro-2-methylcyclohexane CH30 SN2/E2 conditionsarrow_forwardDraw structural formulas for the major product(s) resulting from each step of the following reactions: OH 1. NaH CI-CCH3. Zn(Hg), HNO3 (a) A В D AICI3 HC1 H2SO4 Give major product only 2. CH3CH2CI Give the para product only - ОН OC(CH3)3 В HBr C H202 NBS E (b) A hv H2SO4 CH3 NaOH A MnO2 В Br2 Mg CH3CI. E Br2 F (c) D ether FeBr3 hvarrow_forward
- Draw the major nucleophilic substitution product of each reaction below, showing stereochemistry when necessary. Circle which mechanism type, SNl or SN2, each reaction proceeds by. You do not need to show the mechanisms. CI Но- Syl or SN2 a. Br Snl NANH2 or Sy2 b. DMSO SN1 O Na or Br Acetone Sy2 с.arrow_forwardRank the structures below from the most reactive to the least reactive, in relation to electrophilic aromatic substitution reactions (e.g. nitration)? A Br B OH NO2 E Farrow_forwardI7.00 ☺ السبت ۱ا ديسمبر 1:80 T Compare the following two molecules Enantiomers, diastereomers, or the same? он но HO -H -H- HO". он но- но- -H OH 1 Assign The Chiral Center as R or s HS H2N-CH но Nucleophilic Substitutionarrow_forward
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