Exam (elaborations)
CHM 219 Module 5 questions and answers verified answers||Latest 2024/2025
- Course
- Institution
CHM 219 Module 5 questions and answers verified answers||Latest 2024/2025
[Show more]
Content preview
CHM 219 Module 5Alcohol - ANSGeneric formula R-OH, defined by the presence of a Hydroxyl group (-OH).
Organic derivatives of water, as one of the hydrogen atoms from the water molecule is replaced
by an alkyl group.
Phenols - ANSHydroxyl group directly attached to a benzene ring
Methyl Alcohol - ANSOnly H atoms attached to the carbon bearing the-OH group
Primary Alcohol - ANSone alkyl group attached to the carbon atom bonded to the -OH group
Secondary Alcohol - ANSTwo alkyl groups attached to the carbon atom bonded to the -OH
group
Tertiary Alcohol - ANSThree alkyl groups attached to the carbon atom bonded to the -OH group
Boiling Point of Alcohols - ANSHigh due to Hydrogen bonding between the positively charged H
and negatively charged O
Water solubility of alcohols - ANSAs the carbon chain length increases alcohol becomes
correspondingly less soluble in water.
Alcohols Acidity/Basicity - ANSCan act as a weak base (accepting H+ using a lone pair on the O
atom) or weak acid (donating the O-H proton as H+)
Amphoteric - ANSa substance that can act as both an acid and a base
Alkoxide Ion - ANSconjugate base of an alcohol, very strong base
Alkyloxonium Ion - ANSThe conjugate acid of the alcohol is often called a protonated alcohol,
Dehydration - ANSLoss of water. An alcohol molecule will lose H2O to form an ALKENE. Type
of elimination reaction — lose the -OH from one C and H atom from the adjacent C.
First step — alcohol acts as a base.
Tertiary alcohols - E1
Primary alcohols - E2
All dehydration begins with... - ANSProtonation of the alcohol group.
Order of ease of dehydration of alcohol substrates... - ANS3>2>1
, Tertiary require the least harsh conditions (typically 25% aqueous acid and 60-80 degrees C)
whereas primary require fully concentrated acid and temperatures approaching 200 degrees C.
If more than one alkene product is possible... - ANSThe major product is the one whose C=C
has more alkyl groups attached.
ZAitsev's Rule - ANSThe production of the more highly substituted alkene as the major product.
Alcohols —> Alkyl Halides - ANS-Substitution REaction , replacing the -OH with a halogen
-Alcohol (R-OH) + Hydrogen Halide (H-X) ——> alkyl halide (R-X) + water (H-OH)
-the use of Hydrogen halides promotes the substitution in two ways
1. Acid protonates the -OH of the alcohol to make it a good leaving group
2. Halide ions are good nucleophiles but weak bases so substitution is promoted over
elimination
Order of Reactivity of Alcohols with HX - ANS3>2>1
Primary Alcohols react via.... (With HX) - ANSSn2
-OH group is protonated and then displaced as a water molecule by a chloride ion
Secondary Alcohols react via... (with HX) - ANSSn1 or Sn2 - depending on the structure of the
specific alcohol
Conversion using Phosphorous Halides (PX3) - ANSX= Cl or Br
- Alcohol (3R-OH) + phosphorous trihalide (X2P-X) —> alkyl halide (3R-X) + H3PO3
-particularly efficient as one molecule of PX3 can convert 3 molecules of alcohol to the
corresponding alkyl halide
-byproduct of the reaction is phosphorous acid
Conversion using Thionyl Chloride (SOCl2) - ANSAlcohol (R-OH) + Thionyl Chloride
(Cl-S=O-Cl) —> alkyl Chloride (R-Cl) + SO2 ^ + HCl
- very efficient with primary and secondary alcohols d/t the main byproduct (SO2) beig formed
as a gas and leaving the reaction mixture.
Oxidation to Aldehydes, Ketones and CArboxylic Acids - ANSOxidation - increasing the oxygen
content (number of oxygen atoms) or the oxygen character (more bonds to oxygen)
-Primary Alcohols —> aldehydes —> Carboxylic Acids
-SEcondary Alcohols —>ketones
-Tertiary - unreactive
Jones Reagent - ANSCromium Triioxide with aqueous sulfuric acid —> Chromic Acid
Disadvantage - strong oxidizer and wil not permit the synthesis of aldehydes from primary
alcohols
The benefits of buying summaries with Stuvia:
Guaranteed quality through customer reviews
Stuvia customers have reviewed more than 700,000 summaries. This how you know that you are buying the best documents.
Quick and easy check-out
You can quickly pay through credit card or Stuvia-credit for the summaries. There is no membership needed.
Focus on what matters
Your fellow students write the study notes themselves, which is why the documents are always reliable and up-to-date. This ensures you quickly get to the core!
Frequently asked questions
What do I get when I buy this document?
You get a PDF, available immediately after your purchase. The purchased document is accessible anytime, anywhere and indefinitely through your profile.
Satisfaction guarantee: how does it work?
Our satisfaction guarantee ensures that you always find a study document that suits you well. You fill out a form, and our customer service team takes care of the rest.
Who am I buying these notes from?
Stuvia is a marketplace, so you are not buying this document from us, but from seller QualityPDF. Stuvia facilitates payment to the seller.
Will I be stuck with a subscription?
No, you only buy these notes for $10.49. You're not tied to anything after your purchase.
Can Stuvia be trusted?
4.6 stars on Google & Trustpilot (+1000 reviews)
81989 documents were sold in the last 30 days
Founded in 2010, the go-to place to buy study notes for 14 years now