Ch. 12 - Alcohols, Ethers, Epoxides and ThiolsWorksheetSee 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

Don’t you wish there were a method to convert alcohols into alkyl halides without all these complications? Ah, looks like we’ve got just the reagents for you!

Concept #1: Learning the mechanism of SOCl2

These reagents proceed through SN2 mechanisms, so they will only work on 1° and 2° alcohols. That said, we expect inversion of configuration from this conversion. 

Example #1: Predict the mechanism of PBr3, and draw the final product.   

A few notes regarding the above video:

  • The flow chart being referred to is "The Big Daddy Flowchart" which can be found here – https://www.clutchprep.com/organic-chemistry/sn1-sn2-e1-e2-chart 

 

  • The list of bases we should look out for are: oxides (OR-), alkynides (RC≡C-), NH2-, H-, and ∆ (heat)
Additional Problems
Write a chemical equation for the reaction of 1-butanol with each of the following:  (d) Phosphorus tribromide
Each of the following reactions has been described in the chemical literature and involves an organic starting material somewhat more complex than those we have encountered so far. Nevertheless, on the basis of the topics covered in this chapter, you should be able to write the structure of the principal organic product of each reaction. 
Each of the following reactions has been described in the chemical literature and involves an organic starting material somewhat more complex than those we have encountered so far. Nevertheless, on the basis of the topics covered in this chapter, you should be able to write the structure of the principal organic product of each reaction. 
Draw (with curved arrows) a mechanism for the following reaction:
Propose a mechanism for the formation of 2-bromo-propane from 2-propanol using phosphorus tribromide.
Draw (with curved arrows) a mechanism for the following reaction: 
Provide an organic reaction in which the given intermediate or transition-state structure is involved and give a chemical equation for your selected organic reaction that includes the following in each of your answers: (i) structural formula(s) for the organic reactant(s) [Be sure to show stereochemistry clearly when necessary.]; (ii) a structural formula for the major organic product [Be sure to show stereochemistry clearly when necessary.]; (iii) the experimental conditions (Give structural formulas for organic compounds. Give a chemical formula for inorganic reactants or catalysts . If heat and/or light is needed, be sure to indicate it appropriately.) As we do for most organic reaction equations, the chemical equations that you give do not need to be balanced. Be sure to show stereochemistry clearly when necessary.
Predict the organic product(s) of the following reaction. When appropriate, be sure to indicate stereochemistry. Be sure to indicate the major product if more than one product is formed. Draw all answers in skeletal form. 
Predict the organic product 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. Draw your answer in skeletal form. You will be graded on the product your draw from the reaction no other information is needed for this question.
Predict the organic product 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. Draw your answer in skeletal form. You will be graded on the product your draw from the reaction no other information is needed for this question.
GIVE A SPECIFIC EXAMPLE, WITH MOLECULAR STRUCTURE (no names). If you give more than one example, indicate which one you wish to be graded on. Inorganic reagent that will convert 3-methyl-2-pentanol to 2-bromo-3-methylpentane.
With which reagent is benzoic acid readily converted into benzoyl chloride in high yield?
Predict the product of this reaction
Fill in the boxes provided with the missing intermediate and product. 
Supply a structural formula for the major organic product(s) below. If no reaction occurs, write N.R.
Determine the reagent(s) necessary to complete the reaction below.  
Supply a structural formula for the major organic product(s) below. If no reaction occurs, write N.R.
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 other stereoisomer formed. (enantiomers, diastereomers, etc.).
Predict the products of the following multi-step synthesis: 
Predict the product WITH Stereochemistry:
Predict the organic product(s) of the following reaction. When appropriate, be sure to indicate stereochemistry. Be sure to indicate the major product if more than one product is formed. Draw all answers in skeletal form.  
Which of the following could be used to synthesize 1-bromopentane?A) CH3CH2CH2CH=CH2 + HBr →B) CH3CH2CH2CH2CH2OH + PBr3 →C) CH3CH2CH2CH2CH2OH + NaBr →D) CH3CH2CH2CH2CH2OH + Br2 →E) CH3CH2CH2CH=CH2 + Br2 →
Consider the given alcohols and answer each of the following questionsWhich compound forms an product with an S configuration upon reaction with PBr3? 
Predict the product of the following reaction, showing stereochemistry if applicable.
Draw the major organic product for the following reaction: What type of mechanism is involved in this transformation?SN1, E1, SN2, E2
Draw the major organic product of the reaction shown below. 
What is the major organic product obtained from the following reaction?a. Ib. IIc. IVd. I 
Give the structures of the products you would expect when cis-3-methylcyclopentanol reacts with SOCl2.
What is the major organic product obtained from the following reaction?
Provide the major organic product of the reaction shown.  
Draw the major organic product of the reaction shown below. 
Provide the major organic product of the following. 
What is the missing reagent in the reaction below?