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Review > Review 7 > Flashcards

Review 7 Flashcards

1
Q

What prefix do methanoic acid and methanal share?

A

Form-

  • Methanoic acid = formic acid
  • Methanal = formaldehyde
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2
Q

Prefix “acet-“

A

Two carbon unit with one carbon in carbonyl

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3
Q

Equation for specific rotation

A

Alpha(observed)/(c*l)

  • c = concentration
  • l = path length (in decimeters!)
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4
Q

Larger substituents are more stable as axial or equatorial?

A

Equatorial

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5
Q

Maximum number of stereoisomers a compound can have?

A

2^n

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6
Q

Effect of Sn2 on stereochemistry

A

Inversion - Must attack backside

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7
Q

Rate of Sn2 is dependent on ______

A

Both substrate and nucleophile

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8
Q

Oxidizing primary alcohols (using _____) leads to _____

Oxidizing secondary alcohols => ______

A

1˙ OH + PCC => aldehyde

  • Stronger oxidizing agent => COOH

2˙ OH => ketone

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9
Q

Aldehydes can be oxidized => _____

A

Aldehyde => COOH

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10
Q

Aldehydes, ketones, and carboxylic acids can be reduced to ______ using ______

A

Reduced to OH using LiAlH4

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11
Q

Amides can be reduced to amines using _____

A

LiAlH4

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12
Q

Esters can be reduced to _______ using ______

A

Esters + LiAlH4 => pair of OH

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13
Q

Effect of protic solvents

A

Protonate nucleophile or H bond => inhibit nucleophilicity

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14
Q

Effect of CrO3 or potassium dichromate on primary OH?

A

Oxidize it all the way to COOH

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15
Q

Can you use nonpolar solvents in nucleophile-electrophile reactions?

A

No b/c reactants are polar

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16
Q

Rank carboxylic acid derivatives from most reactive to least

A

Anhydride > COOH + Esters > Amides - Derivatives of higher reactivity can form derivatives of lower reactivity (but not vice versa) - Anhydride can form ester but ester cannot form anhdyride

17
Q

What make good LGs?

A

Weak bases Conjugate bases of strong acids Resonance/induction - Weak bases are more stable in solution

18
Q

Alkyl (carbon) groups are EDG or EWG?

A

C = EDG

19
Q

Why are aldehydes more reactive than ketones?

A

Less steric hindrance

20
Q

Function of acetals/ketals

A

Protect aldehydes/ketones

21
Q

Acetal

A

2 OH + carbonyl - C with 2 OR, R, and an H

22
Q

Phenol + oxidizing agent => _____

A

Quinone (ketones instead of OH) - Does not have to have aromatic ring

23
Q

Convert acetal back to ______ and _____ using ______

A

Carbonyl and two OHs using catalytic acid

24
Q

OH are made into better LG/protected using _____

A

Mesylates (-SO3CH3) and tosylates (SO3C6H4CH3) - Protection is removed using strong acid

25
Q

Jones oxidation components - What does it do?

A

CrO3, dilute sulfuric acid, acetone - Oxidizes 1˙ OH to COOH and 2˙ OH to ketone

26
Q

Oxidation of quinones => ______

A

Hydroxyquinones

27
Q

React one OH w/ carbonyl => _____

A

Hemiketal/hemiacetal

28
Q

HCN + carbonyl => ______

A

Cyanohydrins

  • C attached to OH, R, R, and C triple bonded to N
29
Q

Imines tautomerize to form ______

A

Enamines

30
Q

How are geminal diols formed?

A

Hydration reaction (H2O attacks carbonyl)

31
Q

KMnO4 (potassium permanganate) is a strong _____

A

Oxidizing agent

32
Q

Enolate

A

Carbonyl carbanion/oxanion that lost H bond (has 3 bonds and one LP)

  • Can perform resonance
  • Formed due to base deprotonating alpha carbon from carbonyl compound => carbanion => protonated to form enol
33
Q

Michael addition

A

Carbanion attacks another carbonyl compound w/ a double bond

  • Attacks double bond
34
Q

Aldol

  • Condensation
A

Both aldehyde and OH

  • Aldehyde/ketone enolate (due to deprotonation from base) attacks keto form
  • Usually gets dehydrated (lose OH) in strong base and high temperature
35
Q

Retro-aldol reaction = catalyzed by ______

A

Heat and base

36
Q

LDA (lithium diisopropylamide)

A

Strong base

37
Q

High temperatures and weak base favor which enolate (thermodynamic/kinetic)?

A

Thermodynamic - Proceeds slowly b/c of weak base => kinetic enolate has time to interconvert to thermodynamic

38
Q

Acetone

A

Most basic ketone (H3C - C=O - CH3)

Review (13 decks)

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