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6401 Organic Chemistry Practice Problems

Draw the two major products obtained in the reaction shown. You do not have to consider stereochemistry. You do not have to explicitly draw H atoms

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 In each reaction box, place the best reagent and conditions from the list below. 

HOCH2CH20H, cat. H. NaBHNaOH CH3CH2OH, cat. H+ KMnO4

H2O, H3O+ H2, Pd LiAIH4 CH3CHO, cat. H O3, H2O, Zn OH 

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What is the common name for the following alkyne?

Drawing on what you know about the stereochemistry of alkene addition reactions, write the mechanism for the reaction of 2-butyne with one equivalent Br2

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The reaction below produces two major products: draw one. There is one other major organic product. 

What is its relationship to the compound you drew? 

structural isomer, enantiomer, confomer, diastereomer

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What reagents can be used to form the alkyne product shown from acetylene? 

Select all necessary reagents

CH3l CH3CH2

NaOH 

CH3CH2CH2l

NaH

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Write a structural formula for (Z)-1-cyclopropyl-1-pentene (show stereochemistry as needed).

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What are the products of the following reaction? Draw the molecules on the canvas by choosing buttons from the Tools (for bonds and char choosing the appropriate toolbar buttons and clicking on an atom.


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Draw structural formulas for the diene and dienophile that combine in a Diels-Alder reaction to form the product shown. Consider E/Z stereochemistry of alkenes.

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In each reaction box, place the best reagent and conditions from the list below. 

H2O2, NaOH, H2O CH3Br H2, Pt NaNH2 H2, Lindlar's catalyst 

CrO3, H2SO4, H2O CH3CH2Br NaBH4 NaOH CH3CH2CH2Br BH3/THF


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In each reaction box, place the best reagent and conditions from the list below. 

H2O, H2SO4 (cat.) CH3COO- NaNH2 (excess) H2, Pt Br2 

H2, Lindlar's catalyst BH3/THF PBr3 H2O2, NaOH, H2O CH3CH2OH

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In each reaction box, place the best reagent and conditions from the list below. 

BH3/THF CH3CH2Br NaNH2 H2O2, NaOH, H2O H2, Pt Na, NH3(i) 

CrO3, H2SO4, H2O H2, Lindlar's catalyst CH3CH2CH2Br CH3Br NaBH4 NaOH

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Working backwards, deduce the starting material that led to the indicated product through the defined reactions. 

Draw the reagent A of the following reaction. 

Draw the reagent B of the following reaction.

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 Draw the product of the reaction

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What is the product of the reaction

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For the reaction below: Draw the major organic product in the sketch pad below. 

  • If the reaction produces a racemic mixture, draw both stereoisomers.

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Draw the major product(s) that result from the following reaction. Do not draw inorganic side products.

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Draw the product of the reaction. CH3MgBr [2] H2

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Draw the structure of the product that is formed when the compound shown below is treated with the following reagents: 1) Na, NH3(liq); 2) D2, Pd, including its relative stereochemistry.

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Draw A (Grignard reagent). Draw B (carbonyl compound).

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What epoxide is needed to convert CH3CH2CH2 MgBr to the following alcohol, after quenching with water?

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What Grignard reagent and carbonyl compound can be used to prepare the antidepressant venlafaxine (trade name Effexor)?

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Predict the principal organic product(s) of the following reaction. Specify stereochemistry as is appropriate.

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Draw the major monobromination product when the following alkane is subjected to radical bromination at 25oC If there is more than one product, both may be drawn in the same box


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Draw the major monobromination product when the following alkane is subjected to radical bromination at 25oC If there is more than one product, they both may be drawn in the same box.

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In each reaction box, place the best reagent and conditions from the list below. 

Na, NH3 (I) CH3CH2CH2Br NaBH4 BH3/THF mCPBA

Lindlar's Catalyst CH3Br H2 Pt NaOH, H2O NaNH2 CH3CH2Br

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