(a)
Interpretation: The expected product for the reactions is to be drawn and stereochemistry along with preferred substitution mechanistic pathway between
Concept introduction: Unimolecuar substitution or
The general reaction mechanism for the
Step 1: Formation of a carbocation.
Step 2: Attack of a nucleophile on electron-deficient carbon of a carbocation.
(b)
Interpretation: Whether treatment of
Concept introduction: It has been found experimentally that if the leaving group lies on tertiary carbon than reaction proceeds preferentially via
If the leaving group lies on secondary than both
A good nucleophile can take part in both
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Organic Chemistry: Structure and Function
- Which alkyl halide in each of the following pairs will react faster in an SN2 reaction with OH? Explain your answer briefly. (a) Bromobenzene or benzyl bromide, C6H5CH2B. (b) CH3C1 or (CH3)3CCI (c) CH3CH=CHBr or H2C=CHCH2BRarrow_forwardFor 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_forwardHow will you synthesize cyclohexanecarboxaldehyde (cyclohexylmethanal) from the following reagents? (There are no restrictions on the reagents or the number of steps). (a) Cyclohexanone (b) Ethynylcyclohexane (c) Methyl cyclohexylformate (Remember: Formic acid is the IUPAC recognized name for Methanoic acid) (d) Cyclohexanecarboxylic acid (Cyclohexylmethanoic acid) (e) Vinylcyclohexanearrow_forward
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- 1-Chlorobutane, CH3CH2CH2CH2Cl, reacts with aqueous sodium hydroxide by a second-order nucleophilic substitution reaction, SN2. a) Draw a diagram to show the mechanism of this reactionarrow_forward(i) State one use each of DDT and iodoform.(ii) Which compound in the following couples will react faster in SN2 displacement and why?(a) 1-bromopentane or 2-bromopentane(b) l-bromo-2-methylbutane or 2-bromo-2-methylbutane.arrow_forward4. identify the structure of A and B in the following synthetic scheme: Write out complete reactions for each step, showing the structure of all reactants and products. (a) cyclohexanol +Na2Cr2O7/H2SO4, H2O -------> A (b) A + Et2NH/H2SO4 ----->Barrow_forward
- 7. For each pair of compounds, say which compound is the best SN2 substrate.(a) 2-methyl-1-iodopropane or tert-butyl iodide(b) cyclohexyl bromide or 1-bromo-1-methylcyclohexane(c) 2-bromobutane or isopropyl bromide(d) 1-chloro-2,2-dimethylbutane or 2-chlorobutane(e) 1-iodobutane or 2-iodopropanearrow_forward1 Consider the reaction of (R)-2-chloro-3-methylbutane with sodium iodide to form aproduct.(a) Draw the reaction scheme with the correct stereochemistry (reactant + NaI → product+ NaCl). Circle the nucleophile and draw a rectangle around the electrophile.(b) What is the symbol used for mechanism shown in 1(a)(c) If the sodium iodide was replaced with sodium hydroxide, the product is anALKENE. Draw a reaction MECHANISM to show how this happens.(d) Draw the reaction energy diagram for the reaction in 1(c) and label the activationenergy. (e) Using any alcohol with five carbons, and any carboxylic acid with six carbons, draw areaction to show how we would make an ester.(f) Describe the practical on esters. Please answer (d) to (f)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_forward
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