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Outline a multistep synthesis of the target molecule from the starting material shown.You may use any organic or inorganic reagents.Show the reagents necessary for each step and the product of each step. Outline a multistep synthesis of the target molecule from the starting material shown.You may use any organic or inorganic reagents.Show the reagents necessary for each step and the product of each step.

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Identify the Lewis acid and the Lewis base in the reaction shown here. Identify the Lewis acid and the Lewis base in the reaction shown here.

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Which of the following compounds is the product of the reaction shown that displays retention of configuration compared to the starting material? Which of the following compounds is the product of the reaction shown that displays retention of configuration compared to the starting material? A) B) C) D) E)


A) Which of the following compounds is the product of the reaction shown that displays retention of configuration compared to the starting material? A) B) C) D) E)
B) Which of the following compounds is the product of the reaction shown that displays retention of configuration compared to the starting material? A) B) C) D) E)
C) Which of the following compounds is the product of the reaction shown that displays retention of configuration compared to the starting material? A) B) C) D) E)
D) Which of the following compounds is the product of the reaction shown that displays retention of configuration compared to the starting material? A) B) C) D) E)
E) Which of the following compounds is the product of the reaction shown that displays retention of configuration compared to the starting material? A) B) C) D) E)

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Which of the following ideas best explains why SN2 reactions proceed with inversion of configuration?


A) steric hindrance
B) orbital overlap
C) nucleophile strength
D) solvent effects
E) leaving group ability

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For the reaction profile shown below, which statement(s) could be made? For the reaction profile shown below, which statement(s) could be made? I.The transition state will look more like the starting materials than the products. II.The reaction is endothermic. III.The equilibrium constant for the forward reaction will be larger than 1. IV.The activation barriers for the forward and reverse reactions are equal. A) I only B) I and II C) I and III D) I, II and III E) I, III and IV I.The transition state will look more like the starting materials than the products. II.The reaction is endothermic. III.The equilibrium constant for the forward reaction will be larger than 1. IV.The activation barriers for the forward and reverse reactions are equal.


A) I only
B) I and II
C) I and III
D) I, II and III
E) I, III and IV

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Provide the missing reagents in the following reaction sequence. Provide the missing reagents in the following reaction sequence.

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Which of the following electrophiles would undergo an SN2 reaction with thiolate ion (HS-) at the fastest rate? Which of the following electrophiles would undergo an S<sub>N</sub>2 reaction with thiolate ion (HS<sup>-</sup>) at the fastest rate? A) A B) B C) C D) D E) E


A) A
B) B
C) C
D) D
E) E

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Chemicals such as dimethyl sulfate and iodomethane are considered biologically hazardous because:


A) They can disrupt the body's endocrine system.
B) They are acute respiratory hazards, leading to pulmonary edema.
C) They can alkylate nucleotide bases, leading to mutagenic and carcinogenic effects.
D) They can cause damage to the liver and kidneys.
E) They are corrosive to the eyes and upper respiratory tract.

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What is the most likely stereochemical outcome of the SN1 reaction shown here? What is the most likely stereochemical outcome of the S<sub>N</sub>1 reaction shown here? A) complete inversion of configuration B) complete retention of configuration C) racemization D) more retention than inversion E) more inversion than retention


A) complete inversion of configuration
B) complete retention of configuration
C) racemization
D) more retention than inversion
E) more inversion than retention

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Which of the following statements about Lewis acids and bases is false?


A) Lewis acids are also known as electrophiles.
B) A vacant orbital of a Lewis acid will interact with a filled orbital of a Lewis base to form a sigma bond.
C) All Brønsted bases are also Lewis bases.
D) Typically the LUMO of the Lewis base interacts with the HOMO of the Lewis acid.
E) The reaction of hydride anion with a methyl cation would be an example of a Lewis base/Lewis acid reaction.

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The final step in the SN1 reaction of water with tert-butyl bromide to form tert-butyl alcohol is the deprotonation of the oxonium ion to give the alcohol plus hydronium: The final step in the SN<sub>1</sub> reaction of water with tert-butyl bromide to form tert-butyl alcohol is the deprotonation of the oxonium ion to give the alcohol plus hydronium: The relative energies of the starting materials and products in this step are expected to be very similar. Explain why in practice this reaction proceeds essentially to completion. The relative energies of the starting materials and products in this step are expected to be very similar. Explain why in practice this reaction proceeds essentially to completion.

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In practice this reaction is o...

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Which of these carbocations is most stable? Which of these carbocations is most stable? A) A B) B C) C D) D E) E


A) A
B) B
C) C
D) D
E) E

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Which of the following factors would not be expected to affect the entropy of a reaction?


A) Acyclic reactants are transformed into cyclic products.
B) A weak bond in the reactant is replaced with a strong bond in the product.
C) Two molecules of reactants are transformed into three molecules of products.
D) A double bond in the reactant is converted into a single bond in the product.
E) Gaseous reactants are transformed into solid products.

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What sequence of reactions could be used for the following synthesis? What sequence of reactions could be used for the following synthesis? A) B) C) D) E)


A) What sequence of reactions could be used for the following synthesis? A) B) C) D) E)
B) What sequence of reactions could be used for the following synthesis? A) B) C) D) E)
C) What sequence of reactions could be used for the following synthesis? A) B) C) D) E)
D) What sequence of reactions could be used for the following synthesis? A) B) C) D) E)
E) What sequence of reactions could be used for the following synthesis? A) B) C) D) E)

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An intramolecular Williamson ether synthesis may be used to produce epoxides.Predict the product of the following reaction conditions and provide a mechanism for the transformation. An intramolecular Williamson ether synthesis may be used to produce epoxides.Predict the product of the following reaction conditions and provide a mechanism for the transformation.

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