Ch. 9 - Alkenes and AlkynesWorksheetSee all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins
Sections
Alkene Stability
Zaitsev Rule
Dehydrohalogenation
Double Elimination
Acetylide
Hydrogenation of Alkynes
Dehydration Reaction
POCl3 Dehydration
Alkynide Synthesis
Additional Practice
Hofmann Elimination of Alkyl Fluorides
Debromination
Isomerization of Alkynes
Dissolving Metal Reduction Mechanism
Hydrogenation Retrosynthesis
Alkynide Retrosynthesis
Bredt's Rule
LearnAdditional PracticeSummary

Let's put it all together and provide the expected product.

Example #1: Predict the MAJOR product of the following multistep transformation.  

Example #2: Predict the MAJOR product of the following multistep transformation.  

Let's provide the missing reagents now!

Example #3: Some hints on how to solve the transformation below

Example #4: Using the hints given, provide the reagents to best perform the following transformation. 

Example #5: Using the hints given, provide the reagents to best perform the following transformation. 

Previous SectionPOCl3 Dehydration
Additional Problems
Provide the reagents required for the following transformations. Note, that some of these methods will require more than one chemical step. All the steps and reagents must be included.
What is the major product of this reaction sequence?
Predict the product for the following reaction:
An acetylide ion can also add to carbonyl compounds. Show the product of the following alkyne synthesis by providing the product in it's condensed structural formula and also showing the mechanism. 
Predict the product.
What is the IUPAC name for the expected final product of the transformation below? a) 3-Octyne b) 5-Decyne c) 3-Hexyne d) 5-Octyne e) 1-Octyne
Provide the products for each of the following synthesis. Your products must show stereo- and regiochemistry when necessary; label any chiral carbons with an asterisk.
What is the major organic product obtained from the following reaction?
What is the expected major final product of the reaction sequence shown below?
Consider the strucutres below and answer the following questions. j. Which compound could be prepared from 1-butyne by reaction with LDA/C 2H5I, followed by reaction with sodium in liqiud ammonia in the presense of a proton donor such as ethanol? 
Predict the product of the reaction:  
Determine the mechanism and predict the product of the reaction:
Show how you would perform the following transformation.
Predict the products
Fill in the box with the appropriate reactant, reagent, or product. Some boxes require more than one step.
Predict the products.
Predict the organic product(s) of the following reaction. When appropriate, be sure to indicate stereochemistry. If more than one product is formed be sure to indicate the major product, if stereoisomers are produced in the reaction be sure to indicate the relationship between them. Draw the answer in skeletal form.
Alkene derivatives of pristine (2,6,10,14-tetramethylpentadecane) can be isolated from marine zooplankton and are important in the study of the marine food chain. Which of these routes is best for the preparation of pristane?
Outline the following synthesis and list the reaction in the correct (forward order). (Hint: a retrosynthetic analysis can be very useful) GDE HexcessDGF CDGF ABKF KA
Predict the final product(s) for the following multi-step reaction:
Fill in the missing intermediate, reagent and product for the following synthesis.   
Draw the major organic product(s) of the following reaction.
Provide the product(s) from the following two step reactions.
Predict the organic product(s) for the following reaction. Be sure to indicate stereochemistry when appropriate. If stereoisomers are produced draw one and label the relationship between the stereoisomers. (enantiomers, diastereomers, etc.).
Predict the organic product(s) for the following reaction. Be sure to indicate stereochemistry when appropriate. If stereoisomers are produced draw one and state the relationship between the otherstereoisomer formed. (enantiomers, diastereomers, etc.).
In each reaction box, place the best reagent and conditions from the list below
In each reaction box, place the best reagent and conditions from the list below
Draw the structures of organic compounds A and B. Indicate stereochemistry where applicable.
In each reaction box, place the best reagent and conditions from the list below2 equiv NaNH2, CH3Br, H2O, H2SO4, HgSO4, excess NaNH2, Na, NH3 (l),H2O2, NaOH, H2O, NaBH4, HBr, CH3CH2Br, Br2, PBr3, H2, Lindlar catalyst BH3/THF
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
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
The structure of the product, C, of the following sequence of reactions would be: 
 In each reaction box, place the best reagent and conditions from the list below. 
In each reaction box, place the best reagent and conditions from the list below. PBr H2, Lindlar catalyst BH3/THF excess NaNH2 2 equiv. NaNH2 CH3Br H2O, H2SO4, HgSO4 Na, NH3 H2O2, NaOH, H2O NaBH CH3CH2Br HBr Br2