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CHM 255 Post Exam 3
| Question | Answer |
|---|---|
| Define alcohol | Compound that contains an -OH group attached to an sp3 hybridized carbon |
| Define thiol | Compound that contains an -SH group attached to an sp3 hybridized carbon |
| When naming, how do you number the parent chain? By double bond, triple bond, -x, or -OH | -OH |
| Alcohol nomenclature | add #-ol to the end after the e in the main name |
| Common names: 1. methanol 2. ethanol 3. 1-propanol 4. 2-propanol 5. 1,2-ethanediol | 1. methyl alcohol 2. ethyl alcohol 3. propyl alcohol 4. isopropyl alcohol 5. ethylene glycol |
| Nomenclature for thiols | Main chain that contains SH = alkane+thiol |
| Which has a higher boiling point and why between an alkane and an alcohol | Alcohol because the H-bond interactions are harder to break up |
| Which are more soluble in water and why between an alkane and an alcohol | Alcohol because of their ability to hydrogen bond to water |
| The best way to form alkoxides is ___________ | to treat alcohol with metals (Li, Na, and K) |
| ___>___>___ alcohols at Sn1 | 3o>2o(w/ branching)>1o (won't happen) |
| Primary alcohols proceed through ____ mechanism | Sn2 |
| Why would you want to activate an alcohol | To make it a good leaving group |
| What are Ts/Ms examples of and why would we use them | sulfonates; very good leaving groups |
| How are sulfonates prepared | From alcohols and sulfonyl chlorides in teh presence of a base |
| 3o alcohols will react through ____ mechanism because they are the easiest to dehydrate | E1 |
| 2o alcohols will dehydrate through _______ mechanism but require higher temperatures | E1 |
| 1o alcohols will dehydrate through an ____ mechanism but this reaction is very slow | E2 |
| What is the product of an oxidation of a. 1o alcohol; b. 2o alcohol; c. 3o alcohol | a. aldehyde/carboxylic acid b. ketone c. No rxn |
| What are the oxidizing agents used for alcohols | H2CrO4 PCC |
| Why would you use PCC rather than H2CrO4 to oxidize a 1o alcohol | To stop it at the aldehyde stage |
| The most common oxidation of thiol is ____________________ | The conversion of 2 thiols into a disulfide |
| What is the structure and bond angle of an ether? | C-O-C; 110.3 |
| IUPAC rules for naming and ether | Se4lect the longest parent chain and name the -OR group attached to it as an alkoxy substituent |
| How do the boiling points compare between ethers, alcohols, and alkanes? | Ethers/alkanes << alcohols because of H-bonding in alcohols |
| How does solubility in H2O compare between ethers, alcohols, and alkanes? | Alchohols>ethers>alkanes (none) |
| An ether is an H-bond _______ while an alchol is an H-bond ___________ | acceptor; donor.. can be both |
| Differentiate between common characteristics of H-bond donors & acceptors | Donor: Contain an acidic proton (H); Acceptor: Contain a lone pair of electrons |
| What are the two ways ethers can be prepared? | 1. Williamson Ether synthesis (Sn2); 2. Acid catalyzed addition of alcohols to alkenes (Electrophilic Addition) |
| What is wiliamson ether synthesis and how do you determine how it is accomplished? | Sn2 displacement of a halide ion by an alkoxide; least substituted alkyl halide (1o>2o>3o) is the determiner |
| What is acid catalyzed addition of alcohols to alkenes? | Alkene + acid&alcohol ---> ether (via electrophilic addition) |
| When do you need to use acid base chemistry at the end of a mechanism? | When you use a neutral nucleophile which generates a positive ion |
| What is an epoxide? | 3-membered ring ether |
| What are the two ways to form epoxides? | 1. Sn2 of alkoky halides; 2. Alkene & peroxycarboxylic acid |
| Nomenclature of ethers (common) | List alkyl groups attached to O in alphabetical order and add the word ether to the end |
| Sn2 displacement/opening of epoxide can form what 3 types of compounds? | Nitrile, ether, alkyne |
Created by:
jkmccord11
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