Module 6: Alcohols, Phenols, and Ethers
Structure, Nomenclature, and Classification
Functional Groups at a Glance
In organic chemistry, functional groups determine a molecule’s chemical behavior. Alcohols, phenols, and ethers all involve oxygen atoms, but their chemical and physical properties differ based on how that oxygen is bonded.
| Class | Key Structural Feature | Functional Group | Example |
|---|---|---|---|
| Alcohol | –OH attached to sp³ carbon | Hydroxyl group | CH₃CH₂OH (ethanol) |
| Phenol | –OH attached to aromatic ring | Phenolic group | C₆H₅OH (phenol) |
| Ether | Oxygen bonded to two carbon atoms | Ether linkage | CH₃CH₂–O–CH₃ (ethyl methyl ether) |
MCAT Insight: Recognizing these subtle differences allows you to predict acidity, reactivity, and metabolic transformations of these molecules — all frequently tested on the exam.
Alcohols: Detailed Classification
Alcohols can be categorized based on the type of carbon atom that the hydroxyl group is attached to:
| Type of Alcohol | Description | Structure Example | Common Name |
|---|---|---|---|
| Primary (1°) | –OH on a carbon bonded to 1 other carbon | CH₃CH₂OH | Ethanol |
| Secondary (2°) | –OH on a carbon bonded to 2 other carbons | CH₃CH(OH)CH₃ | Isopropanol (2-propanol) |
| Tertiary (3°) | –OH on a carbon bonded to 3 other carbons | (CH₃)₃COH | Tert-butanol |
Key Concept: This classification impacts:
- Oxidation reactions (only 1° and 2° alcohols can be oxidized under mild conditions)
- Substitution and elimination tendencies (3° alcohols often favor E1/SN1)
Phenols: Unique Reactivity from Aromaticity
Phenols are structurally similar to alcohols but behave very differently due to the conjugation between the lone pair on the oxygen and the π system of the aromatic ring.
Consequences:
- Increased acidity: Phenols are much more acidic than alcohols due to resonance stabilization of the phenoxide ion.
- Electrophilic aromatic substitution: The –OH group activates the aromatic ring toward substitution at the ortho and para positions.
| Example | Functional Group | Notable Properties |
|---|---|---|
| C₆H₅OH | Phenol | Acidic (pKa ≈ 10); antiseptic uses |
| o-nitrophenol | Substituted phenol | Intramolecular hydrogen bonding |
| p-cresol | Methyl-substituted phenol | Occurs in biological systems |
MCAT Tip: Be ready to compare phenols and alcohols in terms of acidity, resonance, and electrophilic reactivity.
Ethers: The Inert Solvent Functional Group
Ethers have an oxygen atom flanked by two carbon chains. They are:
- Relatively non-polar
- Unreactive under many conditions
- Frequently used as solvents in organic reactions
Nomenclature for Ethers
- Common naming:
- List both alkyl groups alphabetically + “ether”
- Example: CH₃–O–CH₂CH₃ → ethyl methyl ether
- IUPAC naming:
- Use the smaller alkyl group as a substituent: “alkoxy” + parent alkane
- Example: CH₃–O–CH₂CH₃ → 1-methoxyethane
| Structure | Common Name | IUPAC Name |
|---|---|---|
| CH₃–O–CH₃ | Dimethyl ether | Methoxymethane |
| CH₃–O–CH₂CH₃ | Ethyl methyl ether | 1-Methoxyethane |
Important Note: Though stable under many conditions, ethers can form peroxides in the presence of oxygen over time, which are highly explosive.
Alcohol, Phenol, and Ether Nomenclature Rules
Alcohols
- Identify the longest carbon chain that contains the hydroxyl group.
- Number the chain to give the –OH group the lowest possible number.
- Replace the “-e” ending of the parent alkane with “-ol”.
- Use “diol” or “triol” for multiple –OH groups.
Examples:
- CH₃CH₂OH → Ethanol
- CH₃CH(OH)CH₃ → 2-Propanol (isopropanol)
- HOCH₂CH₂OH → Ethane-1,2-diol (ethylene glycol)
Phenols
- Always number the aromatic ring with –OH as position 1.
- Use ortho (o-), meta (m-), or para (p-) prefixes if common naming is allowed.
Examples:
- C₆H₅OH → Phenol
- o-nitrophenol → Substituent at position 2 relative to OH
Ethers
- Use either common names or IUPAC “alkoxy” naming.
- For MCAT, be able to recognize both.
Common Pitfalls and Tricks
| Mistake | How to Avoid / Correct It |
|---|---|
| Misclassifying alcohol type (1°, 2°, 3°) | Look at how many other carbons the OH-bearing carbon is attached to |
| Forgetting phenol is not the same as a regular alcohol | Phenols are more acidic and undergo EAS reactions |
| Using wrong naming convention for ethers | Know both common and IUPAC formats |
| Assuming ethers are always unreactive | Watch out for peroxide formation in air-exposed ethers |
Physical Properties and Acidity
Hydrogen Bonding and Boiling Points
One of the defining physical features of alcohols and phenols is their ability to hydrogen bond, a property that has major consequences for boiling point, solubility, and volatility.
Hydrogen Bonding
- Alcohols and phenols both contain an –OH group, which allows them to act as hydrogen bond donors and acceptors.
- This significantly raises their boiling points compared to alkanes, ethers, and other non-polar compounds of similar molecular weight.
- Ethers, lacking –OH groups, cannot hydrogen bond with themselves — but they can hydrogen bond with water.
Boiling Point Comparison (Similar Molar Mass)
| Compound | Boiling Point (°C) | H-Bonding? |
|---|---|---|
| Ethanol (CH₃CH₂OH) | ~78.5 | Yes (strong) |
| Dimethyl ether | ~–24.9 | No (only with water) |
| Propane | ~–42 | No |
MCAT Tip: The presence of hydrogen bonding explains why alcohols and phenols are liquids at room temperature, while ethers and hydrocarbons are often gases.
Solubility in Water
Water solubility depends on a balance between:
- Hydrophilic functional groups (e.g., –OH or ether oxygen)
- Hydrophobic carbon chains
| Compound | Water Solubility | Reason |
|---|---|---|
| Methanol | Completely miscible | Small molecule, strong H-bonding |
| Butanol | Moderately soluble | Increasing hydrophobic tail reduces solubility |
| Hexanol | Poorly soluble | Long non-polar chain outweighs OH group |
| Diethyl ether | Moderately soluble | Can H-bond with water, but weaker overall |
| Phenol | Slightly soluble | Aromatic ring reduces polarity, but OH helps |
Rule of Thumb: ~4–5 carbons is the cutoff for good solubility in water for alcohols.
Acidity: Alcohols vs. Phenols vs. Water
Acidity on the MCAT is about proton donation ability, which is quantified by pKa values:
| Molecule | pKa Value | Relative Acidity |
|---|---|---|
| Strong acids (e.g., HCl) | <0 | Extremely acidic |
| Phenol | ~10 | Much more acidic than alcohol |
| Water | ~15.7 | Baseline |
| Ethanol | ~16 | Slightly weaker acid than water |
| tert-Butanol | ~18 | Even weaker |
| Alkynes (≡CH) | ~25 | Much weaker still |
Why Phenols Are More Acidic:
- When phenol loses a proton (H⁺), the resulting phenoxide ion is resonance-stabilized over the aromatic ring.
- This delocalization of negative charge lowers the energy of the conjugate base, making deprotonation more favorable.
MCAT Favorite: Be able to explain why phenol is a stronger acid than alcohol. It’s about resonance, not just electronegativity.
Key Concepts:
- Inductive effects: Electron-withdrawing groups (e.g., –NO₂, –Cl) near the OH increase acidity.
- Resonance stabilization: Lowers conjugate base energy, increasing acidity.
- Steric hindrance: Bulky groups can reduce solvation of the anion, decreasing acidity.
Common Pitfalls and MCAT Tips
| Misconception | Clarification |
|---|---|
| “All alcohols are very soluble in water” | Solubility drops with chain length |
| “Phenol and alcohols behave the same chemically” | Phenol is aromatic and more acidic |
| “Ethers hydrogen bond like alcohols” | Ethers don’t H-bond with themselves (no OH) |
| “Acidity depends only on OH group” | Resonance and inductive effects are key |
| “Phenol’s conjugate base is unstable” | It’s resonance-stabilized, hence acidic behavior |
Summary Table: Physical Properties at a Glance
| Property | Alcohols | Phenols | Ethers |
|---|---|---|---|
| Boiling Point | High | High | Low (no H-bonding) |
| Solubility (Water) | Good (short chain) | Moderate | Moderate |
| Acidity (pKa) | ~15–18 | ~10 | Weak bases |
| Reactivity | Oxidation, E1/SN1, H-bonding | EAS, acidic | Mostly inert solvent |
Synthesis and Reactions of Alcohols
I. Methods of Synthesizing Alcohols
Alcohols can be synthesized through several key pathways, each of which has mechanistic and regiochemical implications that are heavily tested on the MCAT.
1. Hydration of Alkenes
a. Acid-Catalyzed Hydration (Markovnikov)
$$\ce{CH2=CH2 + H2O ->[H^+] CH3CH2OH}$$
- Reagent: Dilute acid (e.g., H₃O⁺)
- Mechanism: Protonation → carbocation → nucleophilic attack by water → deprotonation
- Regiochemistry: Markovnikov (OH on more substituted carbon)
- Stereochemistry: Can yield racemic mixture (carbocation intermediate)
- Drawback: Possibility of carbocation rearrangement
b. Oxymercuration-Demercuration (Markovnikov, No Rearrangement)
$$\ce{CH2=CH2 ->[1. Hg(OAc)2, H2O][2. NaBH4] CH3CH2OH}$$
- Step 1: Electrophilic addition of Hg²⁺
- Step 2: Water attacks the more substituted carbon
- Step 3: Demercuration with NaBH₄ removes mercury
- Advantage: No carbocation formed → no rearrangement
c. Hydroboration-Oxidation (Anti-Markovnikov)
$$\ce{CH2=CH2 ->[1. BH3][2. H2O2, OH^-] CH3CH2OH}$$
- Step 1: Syn addition of BH₂ and H
- Step 2: BH₂ replaced with OH (oxidation)
- Regiochemistry: Anti-Markovnikov
- Stereochemistry: Syn addition
2. Reduction of Carbonyl Compounds
a. Aldehydes & Ketones → Alcohols
| Carbonyl Compound | Product | Reagents |
|---|---|---|
| Aldehyde | 1° Alcohol | NaBH₄ or LiAlH₄ |
| Ketone | 2° Alcohol | NaBH₄ or LiAlH₄ |
- NaBH₄ is milder, usually used in protic solvents
- LiAlH₄ is stronger, works with esters too (used in ether)
b. Carboxylic Acids & Esters → 1° Alcohols
$$\ce{RCOOH ->[LiAlH4] RCH2OH} \qquad \ce{RCOOR′ ->[LiAlH4] RCH2OH + R′OH}$$
- Requires strong reducing agent (LiAlH₄)
- NaBH₄ cannot reduce these
3. Grignard Reaction: Addition to Carbonyls
Grignard reagents (organomagnesium halides) are strong nucleophiles that attack carbonyls.
$$\ce{R’MgBr + RCHO -> RCH(OH)R’}$$
$$\ce{R’MgBr + RCOR” -> R2C(OH)R’}$$
- Aldehyde → 2° Alcohol
- Ketone → 3° Alcohol
- Formaldehyde → 1° Alcohol
- Must be done under anhydrous conditions
4. Substitution of Alkyl Halides (SN1/SN2)
- 1° and 2° halides can undergo SN2:
$$\ce{R-Br + OH^- -> R-OH + Br^-}$$
- 3° halides can undergo SN1:
- Via carbocation intermediate, yields racemic product
MCAT Tip: Know which mechanism applies depending on substitution level, nucleophile strength, and solvent.
II. Reactions of Alcohols
Alcohols are reactive both as nucleophiles and as electrophiles (after activation). Reactions are often governed by whether you’re oxidizing, substituting, or eliminating the –OH.
1. Oxidation of Alcohols
| Starting Alcohol | Oxidizing Agent | Product |
|---|---|---|
| 1° Alcohol | PCC | Aldehyde |
| 1° Alcohol | KMnO₄, CrO₃ | Carboxylic acid |
| 2° Alcohol | PCC, CrO₃ | Ketone |
| 3° Alcohol | — | No reaction |
- Primary → Aldehyde or Acid (depends on reagent)
- Secondary → Ketone
- Tertiary → Not oxidizable (no H on the carbon with OH)
2. Conversion to Better Leaving Groups
–OH is a poor leaving group, but can be activated:
- Tosylation:
$$\ce{ROH + TsCl -> ROTs}$$
Tosylates = good leaving groups for substitution/elimination.
- Formation of Alkyl Halides:
$$\ce{ROH + HCl -> RCl + H2O}$$
$$\ce{ROH + SOCl2 -> RCl + SO2 + HCl}$$
$$\ce{ROH + PBr3 -> RBr + H3PO3}$$
MCAT Tip: Know that PBr₃ and SOCl₂ replace –OH with halides without rearrangement, unlike HBr.
3. Dehydration (Elimination Reaction)
Alcohols can be dehydrated to form alkenes:
$$\ce{CH3CH2OH ->[H2SO4, heat] CH2=CH2 + H2O}$$
- E1 mechanism for 2° and 3° alcohols (carbocation formed)
- E2 mechanism possible for 1° alcohols under strong acid and heat
- Follows Zaitsev’s Rule (more substituted alkene favored)
4. Esterification
Alcohol + carboxylic acid (or acid derivative) → ester
Fischer Esterification:
$$\ce{ROH + R’COOH <=>[\ce{H^+}] RCOOR’ + H2O}$$
- Reversible
- Requires acid catalyst and removal of water to drive forward
5. Special: Phenol Reactions
Phenols undergo electrophilic aromatic substitution (EAS) much more easily than benzene due to resonance donation from –OH.
Common EAS reactions:
- Nitration
- Halogenation
- Sulfonation
They also form phenoxide salts with strong bases (e.g., NaOH), enabling SN2-like reactions.
Common Mistakes & MCAT Alerts
| MCAT Mistake | Clarification |
|---|---|
| Confusing oxidation levels | Know: 1° alcohol → aldehyde → acid; 2° → ketone; 3° = no reaction |
| Using NaBH₄ on carboxylic acids or esters | Only LiAlH₄ works for those |
| Forgetting rearrangements in acid-catalyzed steps | E.g., dehydration or SN1 can rearrange |
| Forgetting that OH is a bad LG | Must convert to tosylate or alkyl halide before substitution |
| Assuming phenols and alcohols behave identically | Phenols are more acidic and participate in EAS |
Phenols
Overview: What Is a Phenol?
A phenol is a molecule in which a hydroxyl group (–OH) is directly bonded to an aromatic ring, typically a benzene ring. This structural feature gives phenols a unique set of chemical properties that distinguish them from regular alcohols.
General structure:
- Formula: Ar–OH
- Example: C₆H₅OH (common name: phenol)
While phenols resemble alcohols in having an –OH group, their behavior — particularly in acid-base chemistry and electrophilic aromatic substitution — is distinct due to resonance interactions with the aromatic ring.
Acidity of Phenols
Phenols are significantly more acidic than aliphatic alcohols. For example:
$$\ce{pKa_{phenol}} \approx 10$$
$$\ce{pKa_{ethanol}} \approx 16$$
This increased acidity is due to resonance stabilization of the phenoxide ion (Ar–O⁻) formed upon deprotonation.
Resonance Stabilization of Phenoxide:
When phenol loses a proton, the resulting phenoxide anion has its negative charge delocalized across the aromatic ring. This stabilization makes deprotonation more favorable.
Resonance forms of phenoxide include:
- One with the negative charge on oxygen
- Several with the negative charge delocalized to ortho and para positions of the ring
This contrasts sharply with aliphatic alcohols, whose conjugate bases have no resonance stabilization.
Acidity Comparison Table:
| Compound | Conjugate Base | Stabilization Type | Approx. pKa | Relative Acidity |
|---|---|---|---|---|
| Water (H₂O) | OH⁻ | None | 15.7 | Neutral |
| Ethanol (CH₃CH₂OH) | CH₃CH₂O⁻ | None | 16 | Weak Acid |
| Phenol (C₆H₅OH) | C₆H₅O⁻ | Resonance | 10 | Moderate Acid |
| Carboxylic Acid (RCOOH) | RCOO⁻ | Resonance | ~5 | Stronger Acid |
MCAT Insight: The MCAT tests your ability to compare acidity by reasoning through resonance, inductive effects, and hybridization — not by memorizing pKa values. For phenol, you must recognize that aromatic resonance makes it more acidic than most alcohols.
Reactions of Phenols
Phenols undergo several important reactions that distinguish them from regular alcohols:
1. Acid-Base Reactions
Phenols can react with strong bases like NaOH to form phenoxide salts:
$$\ce{C6H5OH + NaOH -> C6H5O^- Na^+ + H2O}$$
- This is useful for extraction: phenol can be selectively deprotonated and separated using aqueous base.
2. Electrophilic Aromatic Substitution (EAS)
The –OH group is an activating, ortho/para-directing group. Phenol reacts readily with electrophiles due to the electron-donating resonance effect of the hydroxyl group.
Common EAS reactions:
- Nitration: C₆H₅OH + HNO₃ →[H₂SO₄] o/p-nitrophenol
- Halogenation: C₆H₅OH + Br₂ → 2,4,6-tribromophenol (no catalyst needed!)
MCAT Tip: Phenol undergoes EAS more easily than benzene. Recognize that electron-donating groups accelerate substitution, especially at ortho and para positions.
3. Oxidation of Phenols
Phenols are susceptible to oxidation, especially under air exposure or in basic conditions. Oxidation can lead to:
- Quinones (e.g. benzoquinone)
- Colored compounds (e.g. due to extended conjugation)
For example:
$$\ce{C6H5OH ->[O] C6H4O2}$$ (benzoquinone)
These reactions are particularly relevant in biochemistry (e.g., redox cycling in coenzymes like ubiquinone).
Summary of Phenol Properties and Reactions
| Property/Reactivity | Phenol Behavior |
|---|---|
| Acidity | More acidic than alcohols due to resonance |
| Solubility | Moderately soluble in water; forms salts with base |
| EAS Reactivity | Highly reactive; ortho/para-directing |
| Oxidation Susceptibility | Easily oxidized to quinones |
| Extraction | Can be separated by acid/base extraction |
Section 4: Ethers — Structure, Properties, and Reactions
I. What Are Ethers?
Ethers are organic compounds in which an oxygen atom is bonded to two alkyl or aryl groups:
- General Formula: R–O–R′
- Ethers are relatively non-polar, have low reactivity, and often act as solvents in organic reactions.
Examples:
- Diethyl ether (CH₃CH₂–O–CH₂CH₃) — a common laboratory solvent.
- Anisole (C₆H₅–OCH₃) — an aryl ether.
II. Nomenclature of Ethers
Ethers can be named in two ways:
- Common Names (used on the MCAT):
- Name both groups attached to oxygen alphabetically + “ether”
- Example: CH₃CH₂–O–CH₃ = ethyl methyl ether
- IUPAC Names:
- Treat the –OR group as an alkoxy substituent on the parent chain.
- Example: CH₃CH₂–O–CH₃ = 1-methoxyethane
MCAT Tip: Recognize both naming systems, but common naming is more frequently tested.
III. Physical Properties of Ethers
| Property | Description |
|---|---|
| Boiling Point | Lower than alcohols (no hydrogen bonding between molecules) |
| Solubility in Water | Moderate, especially for small ethers (can H-bond with water) |
| Polarity | Slightly polar (due to the C–O–C linkage) |
| Reactivity | Generally inert (good solvents for many reactions) |
IV. Synthesis of Ethers
A. Williamson Ether Synthesis
A classic SN2 reaction:
R–O⁻ + R′–LG → R–O–R′
- Requires a strong nucleophile (alkoxide) and a primary alkyl halide
- Secondary or tertiary alkyl halides → elimination instead of substitution
Example:
NaOCH₃ + CH₃CH₂Br → CH₃CH₂–OCH₃ + NaBr
MCAT Insight: Watch for steric hindrance — SN2 only works well with primary alkyl halides.
V. Reactions of Ethers
Ethers are usually inert, but they can undergo cleavage under acidic conditions.
Acidic Cleavage with Strong Acids (HI or HBr):
R–O–R′ + HX → R–X + R′–OH
- Mechanism involves protonation of the ether oxygen, followed by SN1 or SN2 depending on the structure.
- Tertiary, allylic, or benzylic groups favor SN1; methyl and primary favor SN2.
Example:
CH₃–O–CH₂CH₃ + HBr → CH₃Br + CH₃CH₂OH
VI. Special Class: Epoxides (Cyclic Ethers)
Epoxides (three-membered cyclic ethers) are highly strained and reactive. They can undergo ring-opening reactions with:
- Acidic conditions: Attack occurs at the more substituted carbon (SN1-like)
- Basic conditions: Attack occurs at the less hindered carbon (SN2-like)
Example:
Epoxide + H⁺/H₂O → trans-diol
Summary Table: Ethers
| Topic | Key Insight |
|---|---|
| Structure | R–O–R′ (oxygen between two alkyl/aryl groups) |
| Naming | Common: alkyl alkyl ether; IUPAC: alkoxy-alkane |
| Williamson Synthesis | Alkoxide + primary halide → ether (SN2) |
| Acidic Cleavage | Ether + HI/HBr → alkyl halide + alcohol |
| Epoxide Ring Opening | Acid → more substituted; Base → less hindered site |
Laboratory Tests and Synthesis Strategies Involving Alcohols, Phenols, and Ethers
Laboratory Tests to Identify Alcohols, Phenols, and Ethers
MCAT occasionally tests your familiarity with classic lab tests used to distinguish functional groups. Here are the high-yield ones for this module:
1. Lucas Test (Classifies Alcohols)
- Purpose: Distinguishes primary, secondary, and tertiary alcohols.
- Reagent: Lucas reagent (ZnCl₂ in concentrated HCl)
- Mechanism: SN1-like for 2°/3° alcohols; SN2 for 1° (very slow).
- Observation:
- Tertiary alcohol: Immediate turbidity (cloudy layer).
- Secondary alcohol: Turbidity in 5–10 minutes.
- Primary alcohol: No reaction or very slow.
| Alcohol Type | Rate of Reaction | Cloudiness Appears |
|---|---|---|
| 3° (tertiary) | Fast (seconds) | Immediate |
| 2° (secondary) | Moderate (minutes) | After ~5 min |
| 1° (primary) | Very slow | No change |
2. Jones Oxidation (Chromic Acid Test)
- Reagent: CrO₃ in aqueous H₂SO₄ (chromic acid)
- Target Functional Group: Primary and secondary alcohols
- Reaction:
- 1° alcohol → carboxylic acid
- 2° alcohol → ketone
- Positive Test: Orange → green/blue color change
- Tertiary alcohols do not react.
3. Ferric Chloride Test (Phenol Detection)
- Reagent: FeCl₃ (aqueous solution)
- Target Functional Group: Phenols
- Positive Test: Intense color (purple, blue, or green)
- Interpretation: Indicates aromatic hydroxyl group
4. Iodoform Test
- Reagent: I₂/NaOH
- Positive for: Methyl ketones or alcohols that can oxidize to methyl ketones (e.g., ethanol, 2-propanol)
- Observation: Yellow precipitate of iodoform (CHI₃)
- Phenols and ethers give negative results.
Synthesis Strategies Involving Alcohols, Phenols, and Ethers
A. Alcohol Synthesis Pathways
| Target Alcohol Type | Synthesis Method | Reagents |
|---|---|---|
| 1° Alcohol | Reduction of aldehydes/carboxylic acids | NaBH₄ (aldehyde only), LiAlH₄ (both) |
| 2° Alcohol | Reduction of ketones | NaBH₄ or LiAlH₄ |
| 3° Alcohol | Grignard addition to ketones | R–MgX + ketone → 3° alcohol |
| Any Alcohol | Hydroboration or Oxymercuration of alkenes | BH₃/THF, then H₂O₂/NaOH or Hg(OAc)₂/H₂O |
B. Phenol Synthesis Strategies (Less Common for MCAT)
| Method | Reagents/Conditions | Notes |
|---|---|---|
| From Benzene Sulfonic Acid | Fused NaOH, heat | Requires harsh conditions |
| From Diazonium Salt | H₂O, heat | Ar–N₂⁺ → Ar–OH |
| Industrial: Cumene Hydroperoxide | O₂ + H⁺ then hydrolysis | Not tested in detail on MCAT |
C. Ether Synthesis Pathways
| Method | Description | Reagents |
|---|---|---|
| Williamson Ether Synthesis | Alkoxide + primary alkyl halide → ether | RO⁻ + R′–X → R–O–R′ (SN2 reaction) |
| Acid-catalyzed dehydration | 2 alcohols → symmetrical ether | H₂SO₄, heat |
| Alkene addition | Alcohol + alkene (under acid) → ether | ROH + Alkene + H⁺ |
MCAT Strategy Note
- You don’t need to memorize synthetic routes in detail, but you should recognize starting materials, reagents, and expected functional group transformations.
- Reaction recognition, reaction type identification, and interpretation of lab results are fair game on the MCAT.