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DAT > Organic Chemistry > Flashcards

Organic Chemistry Flashcards

1
Q

True or false, the longer the chain length, the higher the boiling point, melting point, and density.

A

True

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2
Q

True or false, the more branching a carbon chain has, the higher the boiling point, melting point, and density.

A

False

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3
Q

What does meso mean?

A

That a molecule with two chiral centers has a plane of symmetry in it. Also, that molecule is superimposable.

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4
Q

What are diastereomers?

A

Types of stereoisomer that are superimposable.

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5
Q

What are enantiomers?

A

Stereoisomers that are superimposable.

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6
Q

A single bond has a ____ bond length and a ____ bond energy than a double or triple bond.

A

Longer, Lower

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7
Q

In the cyclohexane boat configuration, where are substituents preferred to be?

A

In the equatorial position.

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8
Q

Are meso compounds optically active?

A

No

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9
Q

What are racemic mixtures?

A

Mixtures with an even number of R and S chiral centers. There is no optical activity.

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10
Q

Conformational isomers are associated with Newman projections, true or false?

A

True.

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11
Q

Describe the initiation, propagation, and termination steps in free radical halogenation.

A
  • Initiation: Heat is applied to a diatomic halogen forming two free radical halogens.
  • Propagation: One of the free radicals pulls a Hydrogen off an alkane while the other reactions with the carbon forming RX.
  • Termination: Two free radicals react and form a diatomic halogen.
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12
Q

Which carbocations are the most stable? Which free radicals are the most stable?

A

Tertiary carbocations and Tertiary free radicals (•CR3)

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13
Q

Name the five Electrophilic aromatic substitution reactions.

A 
Halogenation
Sulfonation
Nitration
Alkylation
Acylation
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14
Q

What’re vicinal and geminal diols?

A

Vicinal diols are two alcohols on two separate carbons. Geminal means two alcohols on the same carbon.

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15
Q

E1

A

Unimolecular, 2 step, elimination reactions where the rate is dependent upon the substrate. The LG is eliminated forming a carbocation and a Beta proton is removed by a base to form an alkene. Requires polar solvents, good leaving groups, and favors high temperatures.

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16
Q

E2

A

Bimolecular, 1 step, elimination reactions where the rate is dependent upon the substrate and the base. The Base removes a beta proton that is antiperiplanar to the halogen while the halogen is removed simultaneously. The more substituted alkene is preferred.

17
Q

SN1

A

Unimolecular, 2 step, nucleophilic substitution reaction where the rate is dependent upon the substrate. This is favored in protic solvent, it gives racemic products, and prefers more substituted electrophiles.

18
Q

SN2

A

Bimolecular, 1 step, nucleophilic substitution reaction where the rate is dependent upon the substrate and the nucleophile. A strong nucleotide attacks the molecule from the backside releasing the LG and inverting the stereochemistry. This favors aprotic solvents and unhindered molecules.

19
Q

What is the general formula for the amount of carbons and hydrogens on an alkane chain, alkene chain, and alkyne chain?

A

Alkane = C(n) H(2n+2)
Alkene = C(n) H(2n)
Alkyne = C(n) H(2n-2)
where n is the number of Carbon atoms.

20
Q

What is the formula for the degree of unsaturation?

A

Number of double bonds = 1/2 (2n+2-m) where n is the number of carbons and m is number of hydrogens.

21
Q

What factors determine a good nucleophile?

A
  1. Charge-the more negative, the better.
  2. Electronegativity-In protic solvents, the the more electronegative the nucleophile, the worse. In aprotic, the more electronegative, the better.
  3. Sterics-the more bulky a nucleophile, the slower the rate of reaction.
22
Q

Do EWG or EDG’s make something more acidic? Why?

A

EWG make a molecule more acidic because it increases the range of electron delocalization.

23
Q

What are ortho/para activators, ortho/para deactivators, and meta deactivators?

A

o/p activators are EDG such as -OCH3, -OH, and -NH2 that increase the rate of reaction.
o/p deactivators are EWG halogens that decrease the rate of reaction.
meta deactivators are EWG such as -NO2, -COOH, and -CN that also decrease the rate of reaction.

24
Q

What factors determine a good leaving group?

A

Weak bases (or conjugate bases) such as H20, HSO4, Br, Cl, I, and the conjugate base of tosic acid.

24
Q

In mass spec, what does the tallest peak indicate?

A

The tallest peak is the base peak indicating the most common ion.

25
Q

In mass spec, what is the M+ peak?

A

It’s the molecular ion peak, which is the peak with the highest mass/charge ratio.

26
Q

In NMR, deshielding occurs upfield or downfield?

A

Downfield (to the left)

27
Q

In NMR, what is the correlation of the number of peaks to the number of adjacent hydrogens?

A

n + 1 = peaks, where n is the number of adjacent hydrogens.

28
Q

What is the IR spec frequency of a carbonyl group, an ether, an alcohol, an alkane, an alkyne, an Alkene, and an amine?

A 
Carbonyl= 1700
Alcohol =3300 (broad)
Ether=1100
Alkyne=2200, and 3300
Alkane=2900
Alkene =3100
Amine= 3100-3500 (sharp)
Aldehyde= 2800
29
Q

What are epimers?

A

Compounds that have the same optical activity but only differ at one carbon.

30
Q

What are anomers?

A

When the newly formed chiral center differs between 2 of the same cyclic compounds. Alpha is when the OH group is down and beta is when it points up.

31
Q

What’s mutarotation?

A

When there is a change in anomers, such as from alpha to beta.

32
Q

What is the bond called between two monosaccharides? Water is a product.

A

Glycosidic bond

33
Q

How is cellulose linked? What about starch and glycogen?

A

Cellulose is linked via 1,4 beta glycosidic linkages while starch and glycogen are linked via 1,6 alpha glycosidic linkages.

34
Q

In alpha helix structures, where do they hydrogen bonds exist?

A

Between a carbonyl oxygen and a amine nitrogen 4 residues away. An example is keratin.

35
Q

On beta sheets, where are the hydrogen bonds?

A

Between the carbonyl oxygen and an amine nitrogen on different rows.

36
Q

What’s the difference between fibrous and globular proteins?

A

Fibrous proteins, such as collagen, are long strands or sheets. Globular proteins, such as myoglobin, are spherical in shape.

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