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Organic chemistry Flashcards

1
Q

Which among the following was the product produced in Wohler’s synthesis?

A. Ammonium Cyanate
B. Carbon Disulfide
C. Urea
D. Acetic Acid

A

C

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2
Q

Who, among the following constituted the concept of resonance

A. August Kekule
B. Linus Pauling
C. Gilbert Lewis
D. Robert Robinson

A

B

• August Kekulé visualized the ring structure of benzene in 1865

• Gilbert Newton Lewis published his seminal paper suggesting that a chemical bond is a pair of electrons shared by two atoms.
-Lewis Structures

• Robert Robinson - won nobel prize in 1947 for his research on plant dyestuffs (anthocyanins) and alkaloids.
- movement of e- is the driving force for chemical reactions

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3
Q

Which among the following statements, highlights the actual difference between Lewis structures and resonance

a. Lewis structures shows how the atoms of a molecule are bonded to one another while the resonance represents different substituent combinations

b. Lewis structure focuses on the localization of electrons while resonance features the electron capacity of being delocalized

c. Resonance structures represent the various ways in which a molecule can be drawn while the lewis structure represents the accepted true structure of the molecule

d. A resonance structure and lewis structure are virtually indistinguishable from one another

A

B

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4
Q

“True” structure of a molecule

a. Lewis structure
b. Resonance Structure
c. Resonance Hybrid
d. Constitutional Isomer

A

C

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5
Q

Determine whether each of following statements pertaining to constitutional isomers is TRUE or FALSE.

• They have the same molecular formula
• They have the same molecular weight
• They have the same connectivity to their atoms
• They have the same physical properties

A: T, F, F, F
B: T, T, F, F
C: F, T, T, F

A

B

Constitutional Isomer - same molecular formulas, but have different connectivities.

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6
Q

Which among the following statements best describe the most stable conformation of 1-isopropyl-3- methylcyclohexane?

A: The methyl substituent is attached in the equatorial position at C3 and is trans to the isopropyl substituent at C1

B: The isopropyl substituent is attached in the equatorial position at C1 and is trans to the methyl substituent at C3

C: The methyl substituent is attached in the axial position in C3 and is cis to the isopropyl substituent at C1

D: The isopropyl substituent is attached in the axial position at C1 and is cis to the methyl substituent at C3

A

B.

Mas mabigat si isopropyl kaya sya nasa EQUATORIAL

Trans kasi more stable

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7
Q

Which has a higher absolute entropy at a temperature of 25 deg C, cyclopropane or propylene? Why?

A: Both have the same absolute entropy at normal temperature

B: Propylene due to the free rotation around the carbon-carbon single bond

C: Cyclopropane due to the free rotation around the carbon-carbon double bond

D: None of these

A

B

Propylene kasi it has higher mobility bc straight chain lang sya unlike cyclopropane

higher mobility = higher entropy

wala masyado space to move around sa cycloalkane kasi cyclic sya

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8
Q

Which among the following statements is true regarding the boiling point and density of an unsubstituted alkane and a halogen-substituted alkane?

A: Both the boiling point and density of a halogen-substituted alkane is larger than that of its unsubstituted alkane counterpart.

B: Both the boiling point and density of an unsubstituted alkane is larger than that of its halogen-substituted alkane counterpart.

C: The boiling point of an unsubstituted alkane is larger than its halogen substituted counterpart but their density are equal.

D: The density of a halogen substituted alkane is larger than that of its unsubstituted alkane counterpart but their boiling points are the same.

A

A

Halogen substituted alkanes exhibit an INC in SURFACE AREA due to the substitution of a halogen for hydrogen.

The incease in surface area leads to an INC in LONDON DISPERSION FORCES, which then results in a HIGHER boiling point.

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9
Q

Which will rapidly react with hydrogen bromide in order to form its corresponding alkyl bromide?

a. primary
b. secondary
c. tertiary

A

c.

The reaction of alcohols to HX follows
tertiary > secondary > primary > methyl

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10
Q

How is a carbocation stabilized by the alkyl groups attached to it?

A: The alkyl groups release an electron density on the positively charged carbon in order to disperse the positive charge

B: The electrons that are sigma to the positively charged carbon has its orbital overlap with the vacant p orbital of the positively charged carbon

C: The leaving group transfers some of its electrons to the carbocation in order to disperse the positive charge

D: The electrons in the alpha-Carbon hydrogen bonds greatly distributes the positive charge as opposed to the beta- carbon hydrogen bonds

A

A

B: Inductive effect
- positively charged carbon draws the e from the sigma bonds around H

C: There is NO TRANSFER - it attracts the e-

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11
Q

Which among the following reagents will not synthesize cyclohexanol if the starting material is cyclohexene?

A: [1] Diborane, [2] Hydrogen Peroxide, Sodium Hydroxide
B: Bromine and Water
C: Water with Sulfuric Acid
D: [1] 9-BBN, [2] Basic Hydrogen Peroxide

A

B.

Alkene —> alcohol

A. Hydroboration-Oxidation
- produces alcohol
- follows anti- marknovnikovs rule

B. Vicinal Halchydrin Formation
- produces halohydrin + hydrogen halide

C & D. Acid-catalyzed Hydration
- produces alcohol
- uses dilute acid solution
- follows markovnikovs rule

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12
Q

Who among the following proposed the idea correlating Molecular Geometry and Valence Electron Pairs that would later become the Valence Shell Electron Pair Repulsion (VSEPR) Theory?

A: Nevil Sidgwick
B: Ronald Nyholm
C: Herbert Powell
D: Ryutaro Tsuchida

A

B (Ronald Nyholm and Ronald Gillespie)

• Nevil Sidgwick
- demonstrated the existence and wide-ranging importance of the hydrogen bond

• Herbert Powell
- Bakerian lecture with Herbert Marcus Powell correlated molecular geometry with the number of valence electrons on a central atom.

• Ryutaro Tsuchida
- original idea

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13
Q

Linus Pauling introduced the concept of hybridization of orbitals in order to take into account the known geometries of certain compounds, which did not include ____.

A: H2O B: NH3 C: CH4 D: H2S

A

D

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14
Q

What is the Nujol Mull in organic chemical reactions?

A: It is a mass spectrum technique and is obtained by grinding up a solid which is mixed with mineral oil to form a suspension for IR spectroscopy

B: It is the name of a type of paraffin oil from India and most often used in gas chromatography to enhance the mass transfer properties of compounds

C: It is a process applied for inorganic compounds to determine the effervescence of the compound under study

D: It is suspension in mineral oil which is placed in between HgCl, AgI, and KCl, or stainless-steel plates to obtain a good spectrum

A

A

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15
Q

What are sigmatropic rearrangements in organic reactions?

A: They are similar to the (3,3) cope rearrangement where the beta ring of a steroid undergoes photon activated retro- electrocyclization

B: They are thermal reactions which do not allow the formation of six membered benzene ring with a cis or trans alkene such as in the formation of Vitamin D3

C: They are different from electrolytic reactions wherein movement of a sigma bond with a simultaneous rearrangement of the pi-system does not occur

D: They are not the same to the (3,3) cope arrangement and the beta ring does not undergo photon activated retro electrocyclization

A

C

Sigmatropic rearrangements are a type of pericyclic reactions in organic chemistry. These reactions involve the shift of a sigma bond (σ-bond) accompanied by a simultaneous rearrangement of the pi-system (π-system). They are thermally allowed reactions that proceed through a cyclic transition state, without the involvement of ionic intermediates.

Wrong Choices:

a. The (3,3) Cope rearrangement is a specific type of sigmatropic rearrangement, but this choice focuses on a photo-activated retro electrocyclization, which is not part of a general sigmatropic rearrangement definition.

b. This option talks about the formation of six-membered benzene rings and the formation of vitamin D3. While sigmatropic rearrangements are thermal reactions, the specific example provided is not representative of sigmatropic rearrangements in general.

d. This option also contains a typo; it should say “not the same as” instead of “not the same to.” Moreover, it again focuses on the (3, 3) Cope rearrangement and photon activated retro electrocyclization, which does not provide a proper definition of sigmatropic rearrangements in general.

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16
Q

Determine whether each of the following statements is TRUE or FALSE
[a] A molecule containing a stereogenic center automatically indicates that it is a chiral molecule
[b] A molecule with two chirality centers, having an R,S configuration respectively has an enantiomer whose chirality centers have an R,R configuration
[c] A molecule with an S configuration for its single chirality center is bound to display a Levorotatory response when placed in a polarimeter

A:T,T,T
B:T,F,T
C:F,T,F
D:F,F,F

A

D

stereocenter is a point in a molecule, not necessarily an atom. A chiral center is a carbon atom.

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17
Q

A sample of cholesterol, weighing 70.5 mg was submitted to the laboratory to analyze its optical activity. The sample was dissolved in 300 mL of chloroform before placing it in a 25 cm sample tube and inserting it into the polarimeter, installed with a newly bought sodium lamp. If the observed rotation of the plane-polarized light is zero degrees, which among the following is the identity of the sample?

A:100% (+)-cholesterol
B:100% (-)-cholesterol
C:50% (+)-cholesterol
D:50% (-)-cholesterol

A

D

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18
Q

Molecule is not superimposable with its mirror image

a. Chiral
b. Achiral

A

a

• Chirality
- handedness of molecules

• Chiral Center - atom with 4 different groups bonded to it in a tetrahedral orientation

Chiral = nonsuperimposable = posses handedness (isomers)

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19
Q

Achiral molecules with chirality centers

A

Meso compounds

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20
Q

Compounds containing a benzene ring and behaves chemically like benzene

A

Aromatic compounds

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21
Q

Which of the following contains sp-hybridized carbon

a. C4H8
b. C3H6
c. C5H8
d. C6H12

A

c

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22
Q

Bond formed in the head on overlap of two orbitals

a. sigma
b. dative
c. pi
d. double

A

a

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23
Q

Part of molecule where most of its chemical reactions occur

a. single covalent
b. double covalent
c. triple covalent
d. functional group

A

d

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24
Q

Which of the following molecules is unsaturated

a. C3H8
b. CH3OH
c. C5H10
d. CH4

A

c.

Unstaurated = double bond
CnH2n = C5H(2)(5) = C5H10

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25
Q

Which pf the following alkanes is gas at room temperature

a. octane
b. propane
c. eicosane
d. undecane

A

b

ALKANES:
C1-4: gases
C5-17: liquids
C18+ : solids

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26
Q

The rule which states that “In the addition of HX to alkenes the halogen attaches to the doubly bonded carbon with more alkyl substituent

a. Saitsev’s rule
b. Hoffman
c. Markovnikov
d. NOTA

A

c

meaning mag aattach sa may LEAST number of H atoms kasi mas maraming naka attach na alkyl

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27
Q

Hydrogenation of alkynes in the presence of a poisoned palladium catalyst produces

a. alkane
b. alkyne
c. alcohol
d. alkene

A

d

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28
Q

All of the following are ortho and para directing substituents except

a. — OH
b. — F
c. — OR
d. — NO2

A

d

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29
Q

How many isomers does xylene have

a. 1
b. 3
c. 2
d. 4

A

b

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30
Q

Vinylbenzene is also known as

a. styrene
b. cumene
c. mesitylene
d. durene

A

a

31
Q

Hydrocarbon derivatives used as a main ingredient in automobile antifreeze

a. Ethylene glycol
b. Isopropyl alcohol
c. Propylene
d. Toluene

A

a

32
Q

Isomers that are mirror images

a. Constitutional
b. Enantiomers
c. Diastereomers

A

b

33
Q

Isomers that are NOT mirror images

a. Constitutional
b. Enantiomers
c. Diastereomers
d. Conformational

A

C. Diastereomers or non identical isomers

• Conformational - rotational isomers
• Constitutional - structural isomers (same molecular formula but have different bonding atomic organization and bonding patterns)

34
Q

These are isomers that have the same molecular formula and the same arrangement of atoms, but different arrangements of atoms in space due to restricted rotation around a DOUBLE bond.

a. Ligated
b. Enantiomers
c. Conformational
d. Geometric

A

d

• Ligated
- These are isomers that have the same molecular formula and the same arrangement of atoms, but different arrangements of atoms in space due to coordination to a metal ion or molecule.

• Conformational
- These are isomers that have the same molecular formula and the same arrangement of atoms, but different arrangements of atoms in space due to rotations around single bonds.

35
Q

What compound can be used to convert alcohol or a phenol into an ester?

A. Acetic anhydride: CH3-C-O-COCH3
B. Benzamide
C. Maleic anhydrate: CH3-CH2-COO-CH3
D. Aqueous bromine solution

A

A

Wrong choices:

b. Benzamide: Benzamide is an amide, not an acid or an acid derivative, so it cannot be used to form esters from alcohols or phenols.

c. Maleic anhydrate: The provided structure (CH3-CH2-COO-CH3) is incorrect for maleic anhydride. The correct structure for maleic anhydride is a cyclic molecule with the formula C4H2O3. Although maleic anhydride can react with alcohols, it forms mixed anhydrides rather than esters.

d. Aqueous bromine solution: This is a halogenating agent and is not suitable for esterification reactions. Instead, it is used for reactions such as bromination or halogenation of organic compounds.

36
Q

Adrenaline is produced in the body through a biochemical nucleophilic substitution reaction where:

A. The leaving groups are larger and more complex than the halogen atoms frequently in nucleophilic substitution reactions.

B. According to Markovnikov’s rule, the biosynthesis of epinephrine adds hydrogen atoms to the double banded carbon atom.

C. The nucleophilic nitrogen atom of norepinendrine from a covalent bond with the CH3 of S adenosylmethionine

D. The reactant neocleophile atom replaces the leaving group in the nucleophylic substitution reaction.

A

D

Nucleophilic substitution is a fundamental class of reactions in which an electron rich nucleophile selectively bonds with or attacks the positive or partially positive charge of an atom or a group of atoms to replace a so-called leaving group.

• Nucleophiles
- provide e- for making a new bondv
- negatively charged
- nucleus loving

• Electrophiles
- accept e-
- positively charged
- have a polarized pi bond

37
Q

The person’s senses of smell and taste depend on specific biochemic receptors present in a person’s nose and mouth. In 2004, a Nobel prize was given to the researchers who established this fact and identified the type of organic compound associated with the sense of smell and taste.
The chemical identified was;

A. an alcohol
B. rhodopsin
C. an ester
D. an isomer

A

B

Rhodopsin is a G-PROTEIN coupled receptor, and is the most abundant protein in the rod cells found in the RETINA. It functions as the primary photoreceptor molecule of VISION

Wrong choices:

A. An alcohol: Alcohols are a class of organic compounds, but they are not the specific molecules responsible for the sense of smell or taste. Although some alcohols may have a smell or taste, they are not the receptors involved in the detection of these sensations.

C. An ester: Esters are another class of organic compounds that can have characteristic smells or tastes, but they are not the specific molecules responsible for the sense of smell or taste. Like alcohols, they are not the receptors involved in the detection of these sensations.

D. An isomer: An isomer is a term used to describe molecules with the same molecular formula but different arrangements of atoms. Isomers are not a specific class of molecules responsible for the sense of smell or taste, and they do not represent the receptors involved in detecting these sensations.

38
Q

Identify the organic compounds in the following equation: CH3CH(OH)CH2CHO
—> CH3CH = CHO + H20

A. butanol;cis/trans butanol
B. butanoic acid; butanoic acid
C. carbonyl aldehyde; cis or trans-isomer
D. butanol; butaldehyde

A

D

39
Q

These compounds are formed by the reaction of acids with alcohols.

A. Bases
B. Ethers
C. Esters
D. Enzymes

A

C

• BASES are a class of chemical substances that can ACCEPT PROTONS (H+) from acids. This process is known as NEUTRALIZATION, and it typically results in the formation of WATER and a SALT

Neutralization —> water + salt

• ETHERS are organic compounds that contain an oxygen atom bonded to two alkyl or aryl groups. Unlike esters, ethers are not formed by the reaction of acids and alcohols.

• ENZYMES are biological CATALYSTS that accelerate chemical reactions in living organisms. While enzymes can play a role in chemical reactions that involve acids and alcohols, they are not compounds themselves and do not result from the reaction of acids and alcohols.

40
Q

In a dehydration reaction where water is lost, an organic compound C3H8O reacts with concentrated phosphoric and a product is formed. This product rapidly decolorizes a solution of bromine in tetrachlormethane.
What is a product?

A. Propanol
B. Propanolol-2
C. Propene
D. Propanol-1

A

C

Wrong Choices:

A. Propanol: This is the starting reactant, not the product formed after the dehydration reaction.

B. Propanolol-2: This choice seems to be a misspelling or combination of “propanol” and “propranolol,” which is a beta-blocker medication. Neither of them is the correct product.

D. Propanol-1: This is another way to name the starting reactant (propanol) and is not the product formed after the dehydration reaction.

In conclusion, the correct answer is C. Propene, as it is the product formed after the dehydration reaction of propanol in the presence of concentrated phosphoric acid and is capable of decolorizing a bromine solution in tetrachloromethane due to the presence of a double bond.

41
Q

In the deacetylation of acetyl histone, what is the reactant equation?

A. Histone - (CH2) 4-NH3+ +-CH3-COOO
Acetylation Histone – (CH2) 4-NH-C-CH3

B. all of these

C. Histone - (CH2)4-NH3++CH3 - COO acetylation<Histone -(CH2)4-NH-CH -> Deacetylation

D. 2 Histone- (CH2)4-NH3++4 CH3-COO -> 4 Histone- (CH2) 4-2NHO-

A

C

42
Q

Favors formation of less stable carbocations.

a. Anti-Markovnikov’s Rule
b. Markovnikov’s
c. Zaitsev’s
d. Hoffman’s

A

a

• Zaitsev
- The major product in β-elimination reactions is the most highly substituted alkene.
- Favors formation of more substituted alkenes

• Hoffman
- The major product in β-elimination reactions is the least highly substituted alkene.
- Favors formation of less substituted alkenes.

43
Q

The rate of reaction depends on the concentrations of both reactants.

SN2 / SN1

A

SN2

44
Q

The rate of reaction depends on the concentrations of the alkyl halide only.

SN2 / SN1

A

SN1

45
Q

T or F

[1] SN2 and E2 are favoured by a high concentration of a good nucleophile/strong base
[2] SN1 and E1 are favoured by a poor nucleophile/weak base, because a poor nucleophile/weak base disfavours SN2 and E2 reactions

A

T, T

• Alkyl halides undergo two kinds of nucleophilic subtitutions: SN1 and SN2, and two kinds of elimination: E1 and E2.
• SN2 and E2 are bimolecular one-step reactions
• SN1 and E1 are unimolecular two step reactions
• SN1 lead to a mixture of stereoisomers
• SN2 inverts the configuration od an asymmetric carbon
• The major product of a elimination is the most stable alkene
• SN2 are E2 are favoured by strong nucleophile/strong base
• SN2 reactions are favoured by primary alkyl halides
• E2 reactions are favoured by tertiary alkyl halide

46
Q

He won nobel prize in 1947 for his research on plant dyestuffs (anthocyanins) and alkaloids.
- movement of e- is the driving force for chemical reactions

A. August Kekule
B. Linus Pauling
C. Gilbert Lewis
D. Robert Robinson

A

D

• August Kekulé visualized the ring structure of benzene in 1865

• Linus Pauling - resonance

• Gilbert Newton Lewis published his seminal paper suggesting that a chemical bond is a pair of electrons shared by two atoms.

47
Q

Dihedral Angles

  1. Gauche
  2. Anti
  3. Eclipse
A
  1. 60 deg
  2. 180 deg
  3. 0 deg
48
Q

OMEGA 3 ACIDS (3)

A

” A-D-E”

  1. ALA - Alpha linolenic acid (nuts, meat)
  2. DHA - Docosahexaenoic acid (salmon, sardines, tuna)
  3. EPA - Eicosapentaenoic acid (salmon, sardines, tuna)
49
Q

HYDROGENATION CATALYSTS (4)

A
  1. Platinum
  2. Palladium
  3. Nickel
  4. Rhodium
50
Q

What is the chemical formula of Alar?

A. C6H12N202
B. C6H12N203
C. C7H14N203
D. C7H14N202

A

B. C6H12N2O3
• Daminozide

51
Q

Which of the following is a primary application of ethylene?

A. Production of plastics and synthetic fibers
B. Use as a plant hormone for ripening of fruits
C. . Use as a fuel in industrial applications
D. Use as a refrigerant in cryogenic applications

A

B

52
Q

What is another name for lecithin?

A. Phosphatidylcholine
B. Xanthan gun
c. Sodium benzoate
D. Ascorbic acid

A

A.

Lecithin — Phosphatidylcholine
- for food and supplements

53
Q

From which plant is capsaiscin extracted?

A. Cinnamon
B. Capsicum
C. Ginger
D. Turmeric

A

B.

Capsaiscin — Capsicum
- responsible for spicyness

54
Q

Which compound is formed by the reaction of malonic acid and urea with a catalyst, as discovered by Adolf von Baeyer?

A. Indigo
B. Salicylic acid
C. Barbituric acid
D. Acetylsalicylic acid

A

C. Barbituric acid
- used as sedative/hypnotics

55
Q

What structural characteristics do citric acid and malic acid have in common?

A. They are heterocyclic compounds
B. Both has three moieties of carboxylic acid
C. They contain an alkene bridge
D. They are both hydroxy acids

A

D

56
Q

No carbonyl group is found in

a. ether
b. ketone
a. aldehyde
d. carboxylic acid

A

a

57
Q

Which of the following is not an alipatic hydrocarbon?

a. n-octane
b. propylene
c. n-tridecane
d. toluene

A

d. toluene is a cyclic hydrocarbon

• Alipatic - straight chain

58
Q

It is composed of amino acids

a. Carbohydrates
b. Proteins
c. Lipids
d. Nucleic acids

A

b

59
Q

Hydrocarbon derivatives used as a main ingredient in automobile antifreeze

a. ethylene glycol
b. isopropyl alcohol
c. propylene
d. toluene

A

a

60
Q

The, following reagents will give an alkyl halide from an alcohol except

a. Nacl
b. PBr3
c. PCl3
d. SOCI2

A

a

61
Q

Addition of hydrazine to carbonyl compounds produces a/an

a. imine
b. oxime
c. hydrazone
d. semicarbazone

A

c

62
Q

Reduction of alkyl phenyl ketones to aromatic hydrocarbons done by Wolf-Kishner Reduction uses
a. Zn(Hg) , HCl
b. NH2NH2, KOH
c. LiAIH4
d. H2 with Ni or Pt

A

b

63
Q

Hexanedionic acid is also known as

a. malonic acid
b. succinid acid
c. glutaric acid
d. adipic acid

A

d

64
Q

Reaction of alcohol and a carboxylic acid is known as

a. saponification
b. neutralization
c. esterification
d. epoxidation

A

c

65
Q

Addition of an alcohol to acyl halides produces

a. carboxylic acid
b. ester
c. carboxamide
d. none of these

A

b

66
Q

An unknown ester was hydrolyzed with water and acid to produce an acid, x and alcohol, Y. Oxidation of the alcohol with hot KMnO: yielded acid x.
Oxidation of the alcohol produced acetaldehyde. Name the ester.

a. methyl ethanoate
b. ethyl ethanoate
c. methyl propanoate
d. ethyl benzoate

A

b

67
Q

Cyclic esters are known as

a. acetals
b. diglyne
c. lactones
d. osazone

A

c

68
Q

The scent of a banana is due to the ester

a. ethyl formate
b. i-pentyl acetate
c. n-octyl acetate
d. ethyl butyrate

A

b

ester -gives aroma/ scent

69
Q

No carbonyl group is found in

a. aldehyde
b. ketone
c. ester
d. epoxide

A

d

70
Q

OH groups bonded to
vinylic, sp2- hybridized carbons are called

a. tauto
b. enol
c. acetal
d. ketal

A

b

71
Q

Butanoic acid also known as

a. vinegar
b. rancid butter
c. fats
d. cheese

A

b

72
Q

Carboxylic acids are reduced by lithium aluminum hydride to the corresponding

a. primary alcohols
b. secondary alcohols
c. tertiary alcohols
d. All of these

A

a

73
Q

It is a solvent that is a cyclic ether

a. anisole
b. tetrahydrofuran
c. diethylether
d. glycol

A

b

74
Q

Reaction of alcohols with Ag20 directly with alkyl halide forms ether in

a. one step
b. two steps
c. three steps
d. four steps

A

a

ChELE (21 decks)

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