CHM 255 Post Exam 3
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| Define alcohol | Compound that contains an -OH group attached to an sp3 hybridized carbon
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| Define thiol | Compound that contains an -SH group attached to an sp3 hybridized carbon
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| When naming, how do you number the parent chain? By double bond, triple bond, -x, or -OH | -OH
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| Alcohol nomenclature | add #-ol to the end after the e in the main name
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| 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
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| Nomenclature for thiols | Main chain that contains SH = alkane+thiol
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| 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
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| Which are more soluble in water and why between an alkane and an alcohol | Alcohol because of their ability to hydrogen bond to water
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| The best way to form alkoxides is ___________ | to treat alcohol with metals (Li, Na, and K)
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| ___>___>___ alcohols at Sn1 | 3o>2o(w/ branching)>1o (won't happen)
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| Primary alcohols proceed through ____ mechanism | Sn2
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| Why would you want to activate an alcohol | To make it a good leaving group
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| What are Ts/Ms examples of and why would we use them | sulfonates; very good leaving groups
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| How are sulfonates prepared | From alcohols and sulfonyl chlorides in teh presence of a base
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| 3o alcohols will react through ____ mechanism because they are the easiest to dehydrate | E1
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| 2o alcohols will dehydrate through _______ mechanism but require higher temperatures | E1
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| 1o alcohols will dehydrate through an ____ mechanism but this reaction is very slow | E2
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| 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
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| What are the oxidizing agents used for alcohols | H2CrO4
PCC
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| Why would you use PCC rather than H2CrO4 to oxidize a 1o alcohol | To stop it at the aldehyde stage
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| The most common oxidation of thiol is ____________________ | The conversion of 2 thiols into a disulfide
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| What is the structure and bond angle of an ether? | C-O-C; 110.3
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| IUPAC rules for naming and ether | Se4lect the longest parent chain and name the -OR group attached to it as an alkoxy substituent
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| How do the boiling points compare between ethers, alcohols, and alkanes? | Ethers/alkanes << alcohols because of H-bonding in alcohols
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| How does solubility in H2O compare between ethers, alcohols, and alkanes? | Alchohols>ethers>alkanes (none)
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| An ether is an H-bond _______ while an alchol is an H-bond ___________ | acceptor; donor.. can be both
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| Differentiate between common characteristics of H-bond donors & acceptors | Donor: Contain an acidic proton (H); Acceptor: Contain a lone pair of electrons
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| What are the two ways ethers can be prepared? | 1. Williamson Ether synthesis (Sn2); 2. Acid catalyzed addition of alcohols to alkenes (Electrophilic Addition)
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| 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
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| What is acid catalyzed addition of alcohols to alkenes? | Alkene + acid&alcohol ---> ether (via electrophilic addition)
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| 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
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| What is an epoxide? | 3-membered ring ether
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| What are the two ways to form epoxides? | 1. Sn2 of alkoky halides; 2. Alkene & peroxycarboxylic acid
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| Nomenclature of ethers (common) | List alkyl groups attached to O in alphabetical order and add the word ether to the end
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| Sn2 displacement/opening of epoxide can form what 3 types of compounds? | Nitrile, ether, alkyne
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