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Flashcards in Review 7 Deck (38):
1

What prefix do methanoic acid and methanal share?

Form-

- Methanoic acid = formic acid

- Methanal = formaldehyde

2

Prefix "acet-"

Two carbon unit with one carbon in carbonyl

3

Equation for specific rotation

Alpha(observed)/(c*l)

- c = concentration

- l = path length (in decimeters!)

4

Larger substituents are more stable as axial or equatorial?

Equatorial

5

Maximum number of stereoisomers a compound can have?

2^n

6

Effect of Sn2 on stereochemistry

Inversion - Must attack backside

7

Rate of Sn2 is dependent on ______

Both substrate and nucleophile

8

Oxidizing primary alcohols (using _____) leads to _____

Oxidizing secondary alcohols => ______

1˙ OH + PCC => aldehyde

- Stronger oxidizing agent => COOH

2˙ OH => ketone

9

Aldehydes can be oxidized => _____

Aldehyde => COOH

10

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

Reduced to OH using LiAlH4

11

Amides can be reduced to amines using _____

LiAlH4

12

Esters can be reduced to _______ using ______

Esters + LiAlH4 => pair of OH

13

Effect of protic solvents

Protonate nucleophile or H bond => inhibit nucleophilicity

14

Effect of CrO3 or potassium dichromate on primary OH?

Oxidize it all the way to COOH

15

Can you use nonpolar solvents in nucleophile-electrophile reactions?

No b/c reactants are polar

16

Rank carboxylic acid derivatives from most reactive to least

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

What make good LGs?

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

18

Alkyl (carbon) groups are EDG or EWG?

C = EDG

19

Why are aldehydes more reactive than ketones?

Less steric hindrance

20

Function of acetals/ketals

Protect aldehydes/ketones

21

Acetal

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

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22

Phenol + oxidizing agent => _____

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

23

Convert acetal back to ______ and _____ using ______

Carbonyl and two OHs using catalytic acid

24

OH are made into better LG/protected using _____

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

25

Jones oxidation components - What does it do?

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

26

Oxidation of quinones => ______

Hydroxyquinones

27

React one OH w/ carbonyl => _____

Hemiketal/hemiacetal

28

HCN + carbonyl => ______

Cyanohydrins

- C attached to OH, R, R, and C triple bonded to N

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29

Imines tautomerize to form ______

Enamines

30

How are geminal diols formed?

Hydration reaction (H2O attacks carbonyl)

31

KMnO4 (potassium permanganate) is a strong _____

Oxidizing agent

32

Enolate

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

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33

Michael addition

Carbanion attacks another carbonyl compound w/ a double bond

- Attacks double bond

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34

Aldol

- Condensation

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

 

 

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35

Retro-aldol reaction = catalyzed by ______

Heat and base

36

LDA (lithium diisopropylamide)

Strong base

37

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

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

38

Acetone

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