Ch. 14 - Synthetic TechniquesSee 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

Moving Functionality

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Sections
Synthetic Cheatsheet
Moving Functionality
Alkynide Alkylation
Alkane Halogenation
Retrosynthesis

Here will we go into more depth about moving functionality which is important if you want to move non-alkane functional groups on a molecule. 

Concept #1: Moving Functionality in Synthesis

Concept #2: Propose a Synthesis

Concept #3: Propose a Synthesis

Additional Problems
Provide an efficient multistep synthesis for the conversion of the given starting material into the target molecule shown to the right. You must begin with the given starting organic compound. All Cs that  end up in the target compound must come from the given starting organic compound. For each functional group transformation, give all necessary reagents, solvents, and catalysts; give a structural formula for each organic reactant and the major organic product(s). Show stereochemistry appropriately when necessary. If a mixture of products (for example a mixture of stereoisomers) must be present after a step, assume that you can separate the mixture and take the one needed product forward through the next step.
Suggest a sequence of reactions suitable for preparing each of the following compounds from the indicated starting material. You may use any necessary organic or inorganic reagents.  (a) 1-Propanol from 2-propanol 
Suggest a sequence of reactions suitable for preparing each of the following compounds from the indicated starting material. You may use any necessary organic or inorganic reagents.  (b) 1-Bromopropane from 2-bromopropane
Suggest a sequence of reactions suitable for preparing each of the following compounds from the indicated starting material. You may use any necessary organic or inorganic reagents.   (g) tert-Butyl alcohol from isobutyl alcohol 
Suggest a sequence of reactions suitable for preparing each of the following compounds from the indicated starting material. You may use any necessary organic or inorganic reagents.  (h) tert -Butyl iodide from isobutyl iodide 
Provide an efficient multistep synthesis for the following conversion of the given starting compound into the target compound. For this problem, do not give a mechanism with curved arrows. For the synthesis, more than one functional group transformation is required. For each functional group transformation, give all necessary reagents and catalysts and give a structural formula of the organic product. Also give hv and/or heat when necessary. Show stereochemistry appropriately when necessary. 
Show how you would carry out each of the following reactions. You do   NOT need to draw the mechanisms   
Show how you would carry out each of the following reactions. You do   NOT need to draw the mechanisms
Provide a curved arrow mechanism for the following reaction.
Propose an efficient method of converting 3-methyl-1-butanol into 3-methyl-2-butanol.
Fill in the missing reagents:  
Propose a synthetic way to produce the following compound.
Propose a synthetic way to produce the following compound.
Fill in the missing reagents and products.
Provide the reagents necessary to make the indicated product from the indicated starting materials; more than one step maybe necessary.
Propose a synthetic way to produce the following compound.
In each reaction box, place the best reagent and conditions from the list below:NaBH4 in EtOH, BH3 THF, CH3CH2O- HBr, (CH3)3CO-, H2O2/NaOH, Br2 O3 in CH2Cl2, CH3COO-
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.
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. 
 In each reaction box, place the best reagent and conditions from the list below CH3CH2O- HBr CH3COO NaBH4 in EtOH (CH3)3CO- O3 in CH2CI2 Br2
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.
In each reaction box, place the best reagent and conditions from the list below CH3COO- CH3O- H3O+ BH3/THF H2O2, NaOH, H2ONaBH4 NaOH TsCl, pyridine H2SO4 (conc) (CH3)3CO-
In each reaction box, place the best reagent and conditions from the list below. dilute H3O+ NaBH4 H2CrO4 H2O2, NaOH, H2O PBr3,CH3COO- Br2, H2O, (CH3)3CO-, BH3/THF
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.
In each reaction box, place the best reagent and conditions from the list below.