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Mcat > Org Chem > Flashcards

Org Chem Flashcards

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MCAT flashcards
1
Q

Epimer

A

Type of diastereomer where only one chiral center is the opposite configuration in the pair of epimers

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2
Q

Anomer

A

Type of epimer where the anomeric carbon in the sugar is opposite configuration - carbon 1

Epimers that form as a result of ring closure

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3
Q

Mutarotation

A

Equilibrium between anomers

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4
Q

Pyranosee vs furanose

A

6 ring vs 5 ring sugar

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5
Q

Meso compund

A

Internal plane of symmetry

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6
Q

Enantiomer

A

Mirror images

All chiral centers are opposite

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7
Q

Geometric isomer

A

Cis trans isomers or E Z

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8
Q

Constitutional isomers

A

Same formula

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9
Q

Conformational isomers

A

Different spatial arrangement

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10
Q

Difference between cis tans and EZ

A

Cis trans - same groups on same side for cis

E Z - highest priority groups on same side is Z

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11
Q

Lipid bilayer membrane fluidity

A

Cholesterol
Unsaturation
Shorter tails

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12
Q

Steroids

A

Tetracyclic

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13
Q

Glycogen

A

Alpha glucose monomers connected by 1,4 or 1,6 glycosidic linkages

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14
Q

Lactose

A

Galactose + glucose

Beta 1,4

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15
Q

Sucrose

A

Glucose + fructose

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16
Q

Reducing sugar

A

Carbs that can be oxidized by benedicts test

Aldehydes, ketones, hemiacetals

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17
Q

Gabriel malonic ester synthesis

A

Phthalimide + KOH -> phthalimide ion + malonic ester -> Phthalimidomlomic ester which can become all types of amino acid

18
Q

Strecker synthesis

A

Racemic amino acids produced (unlike stereochemically pure L amino acids)

Uses cyanide and ammonium on aldehydes

19
Q

Sn2 mechanism

A 
1 step
Stereochemical inversion
Strong nucleophile
Favored by low substitution of groups
Weak leaving group
Rate law includes nucleophile and electrophile
Polar aprotic solvent (non H bonding)
20
Q

Sn1 mechanism

A 
2 steps
Strong leaving group
Weak nucleophile
Rate law includes electrophile 
Favored by high substitution of groups
Protic solvents

Racemicization

21
Q

Oxidation of primary alcohol

A

Aldehyde via PCC

22
Q

Oxidation of secondary alcohol

A

Ketone via CrO3

23
Q

Alpha vs beta protons

A

Alpha are next to the carbonyl

Beta are one further

24
Q

Nucleophilic Addition to aldehydes and ketones

A

Require reducing agent like NaBH4 to provide hydrogen

25
Q

Grignard reaction

A

Require grignard reagent and acid workup

Produces MgBrOH

26
Q

Cyanohydrin formation

A

Aldehyde or ketone + cyanide ion as nucleophile

27
Q

Imine formation

A

Aldehyde or ketone + primary amine forms imine

28
Q

Enamine formation

A

Aldehyde or ketone + secondary amine

29
Q

Aldol condensation

Crossed aldol?

A

Enol + keto -> hydroxyaldehyde (ketone and hydroxyl without double bond of an enol)

Requires strong base like NaOH

Enol and keto groups from diff carbonyl compound

30
Q

Reduction of carboxylic acid

A

To go to primary alcohol must use LiAlH4 and not NaBH4

31
Q

Transesterification

A

Involve ester and alcohol

32
Q

Saponification

A

TAG is hydrolyzed to glycerol and 3 fatty acids

33
Q

Synthesis of acid halides

A

Carboxylic acid + SOCl/PBr3

34
Q

Acid anhydride formation

A

Two carboxylic acids

35
Q

Relative reactivity of CA derivatives

A

Acid chloride
Acid anhydride
Esters
Amides

36
Q

Extractions

A

Can add acids to convert amines into ions dissolvable in aqueous phase

Can add bases to convert carboxylic acids into salts dissolvable in aqueous phase

37
Q

Deshielding means

A

Electron cloud is more distorted away from the atom

38
Q

NMR

A

Downfield is more deshielded

39
Q

L vs D sugar

A

If hydroxyl of highest numbered chiral carbon is on the left, then it’s an L

40
Q

Carboxylation

A

Addition of COOH

Mcat (7 decks)

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