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CHM 255 Post Exam 3

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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