Organic Chemistry
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Draw an electron-pushing mechanism for the S N2 reaction shown below.
Provide an electron-pushing mechanism for the SN2 reaction shown below.
Draw the structure of the transition state for the S N2 reaction shown below.
Which of the following S N2 reactions would proceed faster? Explain why.
Which of the following haloalkanes would undergo an S N2 reaction more readily?
Which of the following haloalkanes would undergo an SN2 reaction more quickly?
Does a more sterically hindered alkyl halide correspond to a slower or faster SN2 reaction rate?
Determine the products of the following reactions.
a. CH3Br + CH3CH2O−
b. CH3Br + HC≡C−
a. CH3Br + CH3CH2N(CH3)2
b. CH3Br + CH3CH2S−
Determine which alkyl halide is more reactive with a certain nucleophile in an SN2 reaction.
Using (R)-1-deuterio-1-hexanol as the starting material, how could the following be produced?
(R)-1-deuterio-1-methoxyhexane
In an SN2 reaction, sort the given alkyl chlorides from most to least reactive: 1-chloro-3-methylhexane, 1-chloro-2-methylhexane, 2-chloro-2-methylhexane, and 1-chloroheptane.
In an SN2 reaction, determine which alkyl halide is more reactive in each pair of substrates.
For the reaction given below, provide a suitable mechanism that illustrates why the retention of the reactant's configuration at the chiral center is observed in the product.
For the SN2 reactions given below, draw the products formed between:a. (5S)-5-chloro-2,3-dimethylheptane and hydroxide ion
b. 4-bromo-2,6-dimethylheptane and hydroxide ion
What are the structures of the products formed from the given SN2 reactions?
(a) 1-ethyl-3-iodocyclobutane and methoxide ion
(b) 1-chloro-4-isopropylcyclohexane and propoxide ion
The synthesis of 2,3-dihydrobenzo[b][1,4]dioxine-2,3-dicarboxylic acid is illustrated here:
Illustrate the mechanism and determine the intermediate (A).
(a) Illustrate the mechanism by which A is converted to B.
(b) Which is formed faster between A and B?
Which member in each of the given pairs of compounds will undergo SN2 at a faster rate?
Give the substitution products formed in each of the SN2 reactions given below.a. CH3ONa + CH3Br →b.
Give the substitution products formed in each of the SN2 reactions given below.
Determine the major substitution products formed in each of the reactions given below.
Which member in each of the given pairs of compounds is better at SN2 reactions?(a) cyclopentyl iodide or 1-iodo-1-methylcyclopentane(b) tert-butyl bromide or 2-methyl-1-bromopropane
Determine the major substitution products formed in the given reaction.a. CH3C≡C:− Na+ + CH3CH2Br →
Give the major substitution products formed in the given reaction.a. CH3Cl + KCN →
Provide the major substitution products formed in the given reaction.a. 1-Bromobutane + KI →
Allyl chloride is an important industrial compound. Large quantities of allyl chloride are used to produce epichlorohydrin, a precursor to many epoxy resins. Allyl chloride reacts with many nucleophiles to give nucleophilic substitution reactions. An alkyl halide that is similar in structure to allyl chloride is propyl chloride. If both of these compounds react with sodium methoxide, which is less likely to be consumed first?
True or False: The SN2 reaction is the concerted, frontside displacement of a leaving group by a nucleophile. Explain your answer.
Only one equivalent of cyanide will react via substitution with the following dichloroalkane even if applied in excess.
i. Identify the carbon that is expected to be attacked.
ii. Draw the product and justify your answer.
In which solvent does the SN2 reaction below proceed at higher rate? THF or NH3?
Draw the mechanism for the substitution reaction shown below.
Crown ethers can solvate cations as shown below where the 18-crown-6 forms a stable complex with potassium. How is the rate of an SN2 reaction affected by the addition of a crown ether?
Why does the following reaction still occur via an SN2 reaction even though run under standard solvolysis conditions?
Which of the two haloalkanes would undergo SN2 reaction more readily?
Draw the product(s) that would form when the starting organic compound is allowed to react under the given conditions. Write "NR" if there is no reaction.
Predict the product(s) when the following reactions are performed. If no reaction occurs, write "no reaction".
What are the products when the given alcohol is reacted with (a) SOCl2 and (b) PBr3? If there are no reactions, write "No Reaction."
Draw the product(s) that would result when the given molecule is subjected to the following reaction conditions. Write “NR” if there is no reaction.
Provide the mechanism for the SN2 reaction below.
Choose the haloalkane that is expected to react at a faster rate in an SN2 reaction.
Which of the solvents propanol or methyl tert-butyl ether would tilt the equilibrium further to the right? Assume an SN2 mechanism.
How is the relative rate of SN2 expected to change when the reaction below is carried out in a solvent with greater polarity?
What are the products (including stereochemistry) that are produced when the given reagent reacts with the trans configuration of (2-chlorocyclohexyl)(phenyl)sulfane?
How is the relative rate of SN2 expected to change when the reaction shown is carried out in a solvent with greater polarity?
A methyl halide or a primary alkyl halide works best for SN2 reactions. Explain.
The plant metabolite nonadec-1-ene is a positional isomer of nonadec-7-ene. How could you synthesize (Z)-nonadec-7-ene using 2 molecules of 1-bromopropane as one of the starting materials?
How is 1-propanol converted into the compound shown below?
How can 1-propanol be converted to become the ion shown below?
Which solvent between ethanol and acetonitrile makes the propionate ion a better nucleophile in an SN2 reaction with a primary alkyl halide?