Organic Chemistry 332 – Sapling Learning Ch 11

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Using the \"curved arrow\" button, add one or more curved arrows to show the movement of electrons for each step in the following substitution reaction. (All charges and electrons are already drawn.) If needed, click on a drawn curved arrow to change it from double- to single-barbed.

Draw the major organic product(s) of the following reaction (multiple products may be drawn in one box):

Write the structural formula of the main organic product for the following reaction between an alcohol, tosyl chloride, and then a nucleophile.

Draw the major organic product(s) of the following reaction (multiple products may be drawn in one box):

Draw the major organic product formed in the following reaction.

Draw the organic product (if any) expected from the following reaction: (include all hydrogen atoms)

Draw the correct product for the following reaction. (If there is no reaction, draw the starting material.)

Draw the correct organic product for the following oxidation reaction:

Give the product expected when the following alcohol reacts with pyridinium chlorochromate (PCC). (Assume that PCC is present in excess.)

Benzyl ethyl ether reacts with concentrated aqueous HI to form two initial organic products (A and B). Further reaction of product B with HI produces organic product C. Draw the structures of these three products.

Draw the major product formed in the following reaction of an epoxide with acidic methanol.

Use the curved-arrow notation to indicate the flow of electrons in the reaction. (To draw the arrows, click on the reaction to enter the edit mode, then click on the curved-arrow icon.)

Draw the major product formed when the following epoxide reacts with aqueous acid. Use wedge/dash bonds, including H\’s at each stereogenic center, to show the stereochemistry of the product.

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Complete the reaction by writing the correct formula for the missing product.

Draw the organic product of the following nucleophilic substitution reaction. Include the appropriate hydrogen atoms in your structural formula.

Place the best reagent in the bin for each of the following reactions involving cyclohexylmethanol.

A. Predict the organic product of the reaction of 2-methylpropan-1-ol with phosphorus tribromide.

B Phosphorus tribromide makes the oxygen of the alcohol a good leaving group and also provides the nucleophilic bromide. Complete the last step of the mechanism below by using curved arrows.

Draw the major product formed when HBr reacts with the following epoxide.

Draw the major product formed in the following reaction.

Draw the organic product of the following reaction between (1S,3S)-1-chloro-3-methylcyclopentane and methanethiol in the presence of sodium hydroxide.

A. Show any H\’s on chirality centers, if applicable, and use wedge-and-dash bonds.

B. Select all that apply: The product of the reaction is characterized as being

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