Structure & Synthesis of Alcohols and Reactions

These flashcards cover key concepts and reactions related to the structure and synthesis of alcohols, thiols, and their reactions, as outlined in the lecture notes.

What is phenol defined as?

Phenol is defined as OH on an aromatic ring.

What suffix replaces '-e' in alcohol nomenclature?

The suffix that replaces '-e' in alcohol nomenclature is -ol.

What suffix is used for compounds with two OH groups?

The suffix used for compounds with two OH groups is -diol.

What is another name for a 1,2-diol?

A 1,2-diol is also called a glycol.

Which naming system is used for double-substituted phenols?

Double-substituted phenols use the ortho/meta/para naming system.

Why do alcohols have higher boiling points than ethers?

Alcohols have higher boiling points than ethers due to hydrogen bonding.

Alcohol acidity decreases with which factor?

Alcohol acidity decreases with more alkyl groups.

What type of acids are phenols classified as?

Phenols are classified as weak acids.

What do alcohols react with sodium metal to form?

Alcohols react with sodium metal to form alkoxide ions.

What do phenols react with hydroxide to form?

Phenols react with hydroxide to form phenoxide ions.

Alcohols from alkyl halides form by which mechanism?

Alcohols from alkyl halides form by the SN1/SN2 mechanism.

How are alcohols produced via the hydration of alkenes?

Alcohols are produced via the addition of water in the hydration of alkenes.

Hydroboration-oxidation produces alcohols that are classified as?

Hydroboration-oxidation produces alcohols that are anti-Markovnikov.

What does oxymercuration-demercuration yield in terms of alcohols?

Oxymercuration-demercuration yields alcohols that are Markovnikov.

What do organometallic reagents like RMgX and RLi represent?

Organometallic reagents include RMgX and RLi.

What does a Grignard reagent attacking a carbonyl group yield?

A Grignard reagent reacting with a carbonyl group yields a 2° alcohol.

A Grignard reagent reacting with a ketone gives what type of alcohol?

A Grignard reagent reacting with a ketone gives a 3° alcohol.

What does reduction with NaBH₄ reduce?

Reduction with NaBH₄ reduces aldehydes and ketones.

What does LiAlH₄ reduce esters and acids into?

LiAlH₄ reduces esters and acids into 1° alcohols.

What does hydrogenation (H₂/Ni) reduce?

Hydrogenation reduces both C=O and C=C.

What functional group do thiols contain?

Thiols contain the –SH functional group.

What is the –SH group also known as?

The –SH group is also called mercapto.

Thiols are _ acidic than alcohols.

Thiols are more acidic than alcohols.

Thiols are formed via which type of reaction?

Thiols are formed via an SN2 reaction.

What does oxidation refer to in organic chemistry?

Oxidation means loss of H₂ or gain of O/X₂.

What does reduction imply in organic reactions?

Reduction implies loss of O/X₂ or gain of H₂.

What do primary alcohols oxidize into?

Primary alcohols oxidize into aldehydes which can further oxidize to acids.

At what stage does PCC stop the oxidation of alcohols?

PCC stops oxidation at aldehydes.

Secondary alcohols oxidize into which product?

Secondary alcohols oxidize into ketones.

How would you classify ROH as a nucleophile?

ROH is classified as a weak nucleophile.

How would you classify RO⁻ as a nucleophile?

RO⁻ is classified as a strong nucleophile.

What kind of leaving group is OH⁻?

OH⁻ is a poor leaving group.

What kind of leaving group is H₂O?

H₂O is an excellent leaving group.

What mechanism does primary alcohol + HX proceed by?

Primary alcohol + HX proceeds by the SN2 mechanism.

What mechanism does tertiary alcohol + HX proceed by?

Tertiary alcohol + HX proceeds by the SN1 mechanism.

High-temperature dehydration yields what products?

High-temperature dehydration yields alkenes.

What is the mechanism for dehydration at high temperature?

The dehydration mechanism at high temperature is E1.

What does low-temperature dehydration of ROH produce?

Low-temperature dehydration of ROH produces ethers.

What is formed from the reaction of carboxylic acid and alcohol?

Carboxylic acid + alcohol forms an ester.

Which reaction is Williamson ether synthesis associated with?

Williamson ether synthesis is associated with the SN2 mechanism.

Williamson ether synthesis does NOT work with which type of halide?

Williamson ether synthesis does not work with tertiary halides.

What is the formula for ethers?

Ethers have the general formula ROR.

How do the boiling points of ethers compare to those of alcohols?

Ethers have lower boiling points compared to alcohols.

What is required for ether cleavage?

Ether cleavage requires strong acid HX.

In acid-catalyzed epoxide opening, where does the nucleophile attack?

In acid-catalyzed epoxide opening, the nucleophile attacks the more substituted carbon.

In base-catalyzed epoxide opening, where does the nucleophile attack?

In base-catalyzed opening, the nucleophile attacks the less substituted carbon.

What does peroxyacid + alkene yield?

Peroxyacid + alkene forms an epoxide.

What does halohydrin + base yield?

Halohydrin + base forms an ether.

What characterizes a 1,3-diene system?

A 1,3-diene is a conjugated system.

What is true about the stability of the most stable dienes?

Most stable dienes have conjugation.

What has the lowest heat of hydrogenation?

Conjugated dienes have the lowest heat of hydrogenation.

What does allylic position refer to?

Allylic position means one carbon away from a double bond.

What gives rise to 1,2 and 1,4 addition?

1,2 and 1,4 addition comes from carbocation resonance.

What is required for a compound to be aromatic?

Aromatic compounds require planar, cyclic, conjugated, 4n+2 π electrons.

What is the bond order of benzene?

Benzene bond order is 1.5.

What type of reaction do benzene compounds undergo?

Benzene reactions undergo substitution instead of addition.

What forms in the first step of EAS?

A strong electrophile forms in the first step of EAS.

What does sigma complex formation indicate?

The sigma complex (arenium ion) forms during EAS.

How many π electrons does cyclopentadienyl anion have?

Cyclopentadienyl anion has 6 π electrons.

What type of system is cyclopentadienyl anion?

Cyclopentadienyl anion is aromatic.

What is true about tropylium cation?

Tropylium cation is aromatic.

What does a lone pair in an aromatic system imply?

A lone pair in an aromatic system is not basic.

What is the formula for a phenyl group?

The phenyl group is C₆H₅–.

What is the formula for a benzyl group?

The benzyl group is C₆H₅CH₂–.