Concept explainers
(a)
Interpretation:
The mechanism that accounts for the formation of the mixture of the products in a given reaction is to be drawn.
Concept introduction:
Electrophilic addition of the molecular chlorine into but-2-ene gives anti-addition of the molecular chlorine via the formation of the chloronium ion as an intermediate. Under similar conditions, molecular chlorine undergoes both syn and anti-addition to
(b)
Interpretation:
The mechanism for the electrophilic addition of the molecular chlorine to the
Concept introduction:
Electrophilic addition of the molecular chlorine into but-2-ene gives anti-addition of the molecular chlorine via the formation of the chloronium ion as an intermediate. Under similar conditions, molecular chlorine undergoes both syn and anti-addition to
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Chapter 12 Solutions
ORGANIC CHEM. PRIN AND MECHANISM LL+ AC
- (c) The following reaction shows the electrophilic addition reaction between an alkene compound with hydrogen chloride, HCI. Tindak balas berikut menunjukkan tindak balas penambahan elektrofilik antara sebatian alkena dengan hidrogen klorida, HCI. + HCI Major product Draw the mechanism for the formation of major product. Lukis mekanisma bagi pembentukan hasil utama berikut.arrow_forwardFor each reaction, give the expected substitution product, and predict whether the mechanism will be predominantly first order (SN1) or second-order (SN2). (a) cyclohexyl bromide + sodium ethoxidearrow_forward10) Consider the following alkene hydration reaction. он H2SO, H20 Given that the reaction is endergonic by 10 kcal/mol, complete the following. (a) Draw the intermediate(s) formed in the mechanistic pathway to the major product in the indicated space below. If there are multiple intermediates label them 1, 2, 3, 4, etc. (b) Sketch a reaction-energy profile for this reaction and clearly label staring material, product, intermediate(s), transition state(s), AG" and AG (of the rate determining step) on your plot. Progress of the reaction Draw and Label Intermediate(s) Below: Potential energyarrow_forward
- For each reaction, give the expected substitution product, and predict whether the mechanism will be predominantly first order (SN1) or second-order (SN2). (a) isobutyl bromide + sodium methoxidearrow_forwardWhen treated with NaOH, the bromide below gives an alkene by the E2 mechanism, by eliminationof the circled atoms: (a) Draw the Newman projection from which elimination takes place. (b) Draw the mechanism. (c) Draw the product with the proper stereochemistry. (d) Assign the proper stereochemical descriptor to the product. (Z, E? Trans,CiS?) (e)What would happen to the stereochemistry of the product if the enantiomer of the starting material were used inthe reaction?arrow_forwardShow how you would convert(a) oct-3-yne to cis-oct-3-ene.(b) pent-2-yne to trans-pent-2-ene.arrow_forward
- In the reaction (E) 2-methyl -2,4-hexadiene with hydrogen bromide at room temperature, two isomeric products are isolated. Draw the structures for these isomeric products. Which is the kinetic isomer and which is the thermodynamic isomer.arrow_forward(a) Draw the products (including stereoisomers) formed when 2methylhex-2-ene is treated with HBr in the presence of peroxides. (b) Draw the products (including stereoisomers) formed when (S)-2,4dimethylhex-2-ene is treated with HBr and peroxides under similar conditions.arrow_forward(a) What product(s) are formed when the E isomer of C6H5CH = CHC6H5 is treated with Br2, followed by one equivalent of KOH? Label the resulting alkene(s) as E or Z. (b) What product(s) are formed when the Z isomer of C6H5CH = CHC6H5 is subjected to the same reaction sequence? (c) How are the compounds in parts (a) and (b) related to each other?arrow_forward
- For each reaction, draw the complete mechanism and the major organic product(s), paying attention to stereochemistry. (a) (b) OH LOH (еxcess) ? ? CH,Cl2 CH2CI2arrow_forward(a) What product is formed in Step [1] of the following reaction sequence? (b) Draw a mechanism for Step [2] that accounts for the observed stereochemistry. (c) What reaction conditions are necessary to form chiral A from prop-2-en-1-ol (CH2=CHCH2OH)?arrow_forwardWhen acetone is dissolved in either a slightly basic or a slightly acidic solution of oxygen-18 labeled water, H2180, oxygen-18 labeled acetone, (CH3)2C=180, is produced. This is a form of an isotopic exchange reaction between acetone and water. Provide a mechanism to account for this reaction in (a) basic solution and (b) acidic solution. Hint: Is the addition of the nucleophile reversible or irreversible? 180 + H,180 CH3 + Hо `CH3 Acid or base H3C H3Carrow_forward
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