Organic Flashcards

(41 cards)

1
Q

Ketone -> alcohol

A

Sodium borohydride, nucleophilic addition

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2
Q

Making grignard reagent

A

CX + Mg +Ether

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3
Q

Making organolithium

A

CX + 2xLi + ether

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4
Q

Adding alkyl group to ketone

A

nucleophilic addition

1) CMgBr
2) H2O

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5
Q

Ketone + water

A

Hydrate (2 OHs)

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6
Q

Ketone + alcohol

A

Hemiacetal (1 OH and 1 OR)

Nucleophilic substitution

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7
Q

Hemiacetal-> acetal (2×OR)

A

React with alcohol (acidic conditions)

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8
Q

Acid catalysis

A

Carbonyl more electrophilic

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9
Q

Base catalysis

A

Nucleophile more nucleophilic

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10
Q

Acid chloride -> ester

A

RO- =nucleophile

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11
Q

Stabilisation of anions

A

1) electronegative elements
2) delocalisation of -ve charge
3) strength of A-H bond(weaker= more stable)

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12
Q

Reactivity of carbonyl group

A

1) Inductive effect- neighbouring electronegative groups, increased reactivity
2) Conjugative effect- conjugation=less reactive

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13
Q

Ester -> alcohol (reduction)

A

LiAlH4- strong, not aqueous

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14
Q

Acid chloride -> alcohol (reduction)

A

NaBH4- quite weak

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15
Q

Carboxylic acid -> alcohol (reduction)

A

Borane (BH3)- strongest

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16
Q

Reduction of amide

A

LiAlH4

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17
Q

RX -> carboxylic acid

A

Make grignard, then react with CO2

18
Q

Carbonyl derivative -> carboxylic acid

A

Add water (hydrolysis) acid or base mediated

19
Q

Carboxylic acid derivative -> ester

A

Alcohol (acid mediated only)

20
Q

Steric hindrance and Sn1

A

More substituents = more likely, fabrication more stable

21
Q

Steric hindrance and Sn2

A

More substituents= less likely- approach of nucleophile more difficult

22
Q

Hyperconjugation

A

Sn1 only, no. of groups attached increases reactivity

23
Q

Pi bond and lone pair donation

A

Sn1 only
Pi=conjugation, more stable
Lone pair donation strongest

24
Q

Adjacent double bonds

A

Sn2 only

Stabilises transition state

25
Adjacent carbonyl group
Sn2 only | Anti-bonding adjacent to centre withdraws electrons, stabilises transition state
26
Sn1 stereochemistry
Racemic mixture
27
Sn2 stereochemistry
Single enantiomer
28
R-OH -> R-OTs (sulphonate ester)
``` Tosyl Chloride (TsCl) and pyridine (Py) Improves leaving group ability of OH ```
29
Epoxides
More reactive version of ethers
30
Solvent for Sn1
Polar, peptic Stabilises ions formed H2O, Ethanol
31
Solvent for Sn2
Polar, aprotic Anions are nucleophiles, must be allowed to react Acetone, DMSO
32
E1 stereochemistry
Trans=major, cis=minor
33
E2 stereochemistry
Cis only- C-H and C-X must be antiperiplanar
34
Strength of base - elimination or substitution
Strong=elimination | Weak=substitution
35
Temp and elimination
High temp favours elimination
36
Size of nucleophile and elimination
Steric hindrance favours elimination
37
Bromination stereochemistry
Trans
38
Halohydrin formation
Large amount of water with Br2, trans product
39
Epoxidation
Alkene precursor and m-CPBA | Or halohydrin and NaH
40
Hydroboration
Adds water with opposite regioselectivity 1) BH3 2) H2O2, NaOH, H2O
41
Reducing agent order of reactivity
NaBH4