Org Chem Flashcards by Zed D

which of the following describes a triple bond?
* 2 sigma bonds and 2 pi bonds
* 3 pi bonds
* 2 sigma bonds and 1 pi bond
* 1 sigma bond and 2 pi bonds

1 sigma bond and 2 pi bonds

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Which of the following may be separated by ordinary physical
methods?
a. (R)-3-bromo-1-butene and (S)-3-bromo-1-butene
b. cis-2-bromo-2-butene and trans-2-bromo-2-butene
c. (2R,3S)-1,2-dibromobutane and (2S,3R)-1,2-dibromobutane
d. (R)-2-bromobutane and (S)-2-bromobutane

b. cis-2-bromo-2-butene and trans-2-bromo-2-butene

enantiomers cannot be separated by physical methods

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Which of the following physical properties differ for each of a pair of enantiomers?
a. solubility in ethanol
b. direction of rotation of plane-polarized light
c. boiling point and melting point
d. index of refraction

b. direction of rotation of plane-polarized light

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Explain the differences in structure between a saturated hydrocarbon from an unsaturated hydrocarbon.
a. Any of these
b. A saturated hydrocarbons contains only carbon-carbon single bonds,
while an unsaturated hydrocarbon contains one or more carbon-carbon
double or triple bonds.
c. A saturated hydrocarbon is used mainly in cheaper forms of gasoline for
vehicle use, while unsaturated hydrocarbons composed most of the
gasoline formulas, used by current gasoline manufacturers.
d. A saturated hydrocarbon can no longer accept any hydrocarbon or
inorganic element and compound, while an unsaturated hydrocarbon is
more of flexible in reaction mechanisms.

b. A saturated hydrocarbons contains only carbon-carbon single bonds,
while an unsaturated hydrocarbon contains one or more carbon-carbon double or triple bonds.

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Which of the following best explains the relative stabilities of the
eclipsed and staggered forms of ethane? The __________ form has the
most __________ strain.
a. eclipsed; steric
b. eclipsed; torsional
c. staggered; steric
d. staggered; torsional

b. eclipsed; torsional

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R-2-pentanol and S-2-pentanol are different with respect
to their:
a. boiling point
b. melting point.
c. direction of rotation of plane-polarized light.
d. number of degrees of rotation of plane-polarized light
e. Choices C and D are both correct

c. direction of rotation of plane-polarized light

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A and B are stereoisomers. They are nonsuperimposable and are
mirror images of one another. Which of the following best describes
the relationship between A and B?

enantiomers

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A nucleophile acts as a ________ when it reacts with an electrophile.
a. Bronsted-Lowry acid
b. Arrhenius base
c. Lewis acid
d. Lewis base

d. Lewis base

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Which of the following is/are optically inactive?
a. a 50-50 mixture of R and S enantiomers
b. a meso compound
c. every achiral compound
d. a racemic mixture
e. all the above

e. all the above

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Which of the following is not a nucleophile?
a. FeBr3
b. Br
c. NH3
d. benzene
e. CH3OCH3

a. FeBr3

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Which of the following are the substitution products of the reaction
shown below?
CH3CH2Br + -OH → ?
a. CH3CH2Br + H + O
b. HOCH2CH2Br
c. CH3CH2OH + Br
d. CH2=CH2 + Br- + H2O
e. CH2=CHBr- + H2O

c. CH3CH2OH + Br

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Which of the following statements is (are) true about an SN2 reaction?
a. The reaction is fastest with 1° halides.
b. The reaction follows second-order kinetics.
c. Changing the identity of the leaving group changes the rate of the
reaction.
d. Only Statements A and B are true.
e. Statements A, B, and C are all true.

e. Statements A, B, and C are all true.

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Rank each of the following halides in order of increasing reactivity in
an SN2 displacement reaction.
1. (CH3)2CHCI 2. CH3CH2Br 3. CH3CH2CI
a. 1; 2; 3
b. 3; 2; 1
c. 1; 3; 2
d. 2; 1; 3
e. 3; 1; 2

c. 1; 3; 2

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Which of the following SN2 reactions is the slowest?
a. CH3CH2CH2Br + HO- → CH3CH2CH2OH + Br
b. CH3CH2CH2Cl + HO- → CH3CH2CH2OH + Cl
c. CH3CH2CH2I + HO- → CH3CH2CH2OH + I
d. CH3CH2CH2F + HO- → CH3CH2CH2OH + F

d. CH3CH2CH2F + HO- → CH3CH2CH2OH + F

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Williamson synthesis is a procedure for the production of:
a. Esters from acid chlorides
b. Alkanes using sodium metal
c. Ethers from alkyl iodide
d. Salicylic acid from phenol

c. Ethers from alkyl iodide

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Which of the following statements is NOTTRUE?
a. Alcohols are weakly acidic
b. Alcohols are weakly basic
c. Alcohols form alkoxide ions when reacted with a strong base
d. Alcohols are reversibly protonated by strong acids to yield oxonium
ions ROH2+
e. Electron withdrawing groups decrease the acidity of alcohols.

e. Electron withdrawing groups decrease the acidity of alcohols.

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The Lucas test is used to determine the types of
a. alcohols
b. amines
c. acids
d. amino acids
e. phenols

a. alcohols

used to classify if alcohol is 1°, 2°, 3°

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Tollen’s test

Aldehydes

magkakaroon silver precipitates to denote presence of aldehydes

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Iodoform Test

methyl ketone

determine if methyl ketone or not

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2,4 - dinitrophenylhydrazine
Test

carbonyl compounds

detect presence of carbonyl group (nagtuturn yellow)

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Which of the following reagents can be used to oxidize 1° alcohols to
aldehydes?
a. KMnO4
b. MnO2
c. K2Cr2O7
d. H2O2
e. PCC

e. PCC

mild oxidizing agent
PCC - pyrodine chlorochromate

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Secondary alcohol when undergoes oxidation forms
a. aldehydes
b. acid
c. ketone
d. ester

c. ketone

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The alkene formed is the one that is more alkyl substituted.
a. Markovnikoff’s Rule
b. Saitsev’s Rule
c. Hoffman’s Rule
d. Huckel’s Rule

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b. Saitsev’s Rule

opposite is Hoffman

primary alcohol when undergoes oxidation by strong oxidizing agent forms

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carboxylic acid

example of strong is CrO4-

What is the major product from the acid-catalyzed hydration of 2 methyl-2-pentene? a. 2-methylpentane b. 2-methyl-1-pentanol c. 2-methyl-2-pentanol d. 2-methyl-3-pentanol

c. 2-methyl-2-pentanol

Isobutyl alcohol can be produced from isobutene through what reaction? a. acid catalyzed hydration b. oxymercuration/demercuration c. hydroboration/oxidation d. all of these

c. hydroboration/oxidation | anti - M

A reaction sequence used to achieve anti-Markovnikov hydration of an alkene; initiated by concerted syn addition of borane, followed by oxidation with basic hydrogen peroxide a. Oxidation b. Oxymercuration-Demercuration c. Ozonolysis d. Hydroboration-Oxidation

d. Hydroboration-Oxidation

The ozonolysis product/s obtained from all the unbranched and unsymmetrical isomers of heptene is/are a. a single aldehyde b. an aldehyde and a ketone c. two different ketones d. two different aldehydes

d. two different aldehydes

Ozonolysis (O3 in CH2Cl2) of compound A under reducing conditions (Zn /acetic acid) gives formaldehyde, 2-butanone, and compound B. Catalytic hydrogenation (H2/Pd) of A gives 2,7-dimethylnonane. What is a possible structure for compound A? a. 2,7-Dimethyl-2,8-nonadiene b. 2,7-Dimethyl-1,8-nonadiene c. 2,7-Dimethyl-1,6-nonadiene d. 2,7-Dimethyl-1,7-nonadiene

c. 2,7-Dimethyl-1,6-nonadiene

Which of the following reagents will not yield an alcohol from an alkene? a. OsO4/NaHSO3 b. Br2/H2O c. H+/heat d. KOH/CH3CH2OH

d. KOH/CH3CH2OH | a: syn - dihydroxylation b: add of 2X c. add of OH (Acid Cat hydration) ## Footnote alkyl halide dat ang compound to produce alcohol if using d.

Which of the following compounds is the major product when 1 hexyne is treated with excess HBr? a. 1,1-dibromohexane b. 1,1-dibromohexene c. 1,2-dibromohexene d. 1,2-dibromohexane e. 2,2-dibromohexane

e. 2,2-dibromohexane

Hydration of alkynes yields a. epoxide b. ketone c. alcohol d. ether

b. ketone

The reagent needed to convert 2-butyne to cis-2-butene is

H2/Lindlar's catalyst

The reagent needed to convert 2-butyne to trans-2-butene is

Li/NH3

The reagent needed to convert 2-butyne to butane is

2H2/Pt

Hydrolysis of an ester leads to two compounds. Which of the following pairs compounds is formed from such a hydrolysis? a. An alcohol and an aldehyde b. An alcohol and a carboxylic acid c. Two alcohols d. A ketone and a carboxylic acid

b. An alcohol and a carboxylic acid

What compound can be used to convert alcohol or a phenol into an ester? a. Acetic anhydride: CH3-C-O-COCH b. Benzamide c. Maleic anhydrate: CH3-CH2-COO-CH3 d. Aqueous bromine solution

a. Acetic anhydride: CH3-C-O-COCH | dat carboxylic acid or derivatives

An acid chloride forms an ester by which of the following reactions? a. reduction b. oxidation c. hydrolysis d. alcoholysis

d. alcoholysis

What organic product is formed when C6H5CH2COOH is treated with CH3OH + H2SO4 (catalyst)? a. C6H5CH2CH2OH b. C6H5CH2COO-Na+ + CO2 + H2O c. C6H5CH2COO-NH4 d. C6H5CH2COOCH3+ H2O

d. C6H5CH2COOCH3+ H2O

An unknown ester, C6H12O2 was hydrolyzed with water and acid to produce acid X and alcohol Y. Oxidation of Y with chromic acid produced X. What was the structure of the ester? a. ethyl ethanoate b. propyl propanoate c. butyl ethanoate d. ethyl butanoate

b. propyl propanoate

Which of the following correctly ranks the cycloalkanes in order of increasing ring strain per methylene? a. cyclopropane < cyclobutane < cyclohexane < cycloheptane b. cyclohexane < cyclopentane < cyclobutane < cyclopropane c. cyclopentane < cyclobutane < cyclopentane < cyclopropane d. cyclopentane < cyclopropane < cyclobutane < cyclohexane

b. cyclohexane < cyclopentane < cyclobutane < cyclopropane

Consider the three isomeric alkanes n-hexane, 2, 3-dimethylbutane, and 2-methylpentane. Which of the following correctly lists these compounds in order of increasing boiling point? a. 2,3-dimethylbutane < 2-methylpentane < n-hexane b. 2-methylpentane < n-hexane < 2,3-dimethylbutane c. 2-methylpentane < 2, 3-dimethylbutane < n-hexane d. n-hexane < 2-methylpentane < 2,3-dimethylbutane

a. 2,3-dimethylbutane < 2-methylpentane < n-hexane

Predict which of the following compounds will have a lower boiling point than 1-butanal. a. 1-butanol b. 2-butanol c. 1-butene d. butanoic acid

c. 1-butene ## Footnote yung walang electronegative element electronegative makes cmp polar if polar - pdd if may OH - H bonding

In the study of fats and lipids, determine which of the two triglycerides has a higher melting point, substance A containing only lauric acid and glycerol, or substance B containing only stearic acid and glycerol? a. В b. A c. Both have the same melting point d. None of these

a. В | stearic - C18 lauric - C12

Which of the following is the most soluble in H2O? a. CH3OCH3 b. CH3CH2OH c. CH3CH2Cl d. CH3CHO

b. CH3CH2OH

Which of the following is the electrophile that attacks the aromatic ring during nitration? a. NO2 b. HNO3 c. NO2 d. NO2+

d. NO2+ | dat + charge or ndi - charge and wala lone pair

What is the major organic product of the reaction between benzene and isobutyl chloride in the presence of AlCl3? a. tert-butylbenzene b. isobutylbenzene c. n-butylbenzene d. sec-butylbenzene

b. isobutylbenzene

In electrophilic aromatic substitution reactions a chlorine substituent: a. is a deactivator and a m-director. b. is a deactivator and an o,p-director. c. is an activator and a m-director. d. is an activator and an o,p-director. e. none of the above

b. is a deactivator and an o,p-director.

Which of the following compounds reacts most rapidly with HNO3/H2SO4? a. toluene b. anisole c. nitrobenzene d. benzonitrile e. fluorobenzene

b. anisole

Starting with benzene, the best method for preparing p- nitrobenzoic acid is: a. HNO3/H2SO4; then CH3CI/AICI3; then separation of isomers; then KMnO4/ OH/heat, followed by H3O+. b. CH3CI/AICI3; then HNO3/H2SO4; then separation of isomers; then KMnO4/ OH/heat, followed by H3O+. c. CH3CI/AICI3; then KMnO4/-OH/heat, followed by H3O+; then HNO3/H2SO4. d. HNO3/H2SO4; then KMnO4/-OH/heat, followed by H3O+; then CH3CI/AICI3. e. HNO3/H2SO4; then CO2, followed by H3O+.

b. CH3CI/AICI3; then HNO3/H2SO4; then separation of isomers; then KMnO4/ OH/heat, followed by H3O+.

Taurine, a Beta amino acid belongs to the acidic group of: a.–SO2OH b.–COOH c.–COONH3 d.–C=OH

a. –SO₂OH ## Footnote Taurine contains a sulfonic acid group (–SO₂OH), which makes it acidic. It's a beta-amino acid because the amino group is on the β-carbon (second from the acid group).

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

c. an ester | Esters are responsible for many scents and flavors.

What type of polymer is used for bulletproof vests? a. Linear polyethylene fiber b. Polyacrylonitrate fiber c. Polycarbonate fiber d. Polymethacrylate fiber

a. Linear polyethylene fiber ## Footnote Ultra-high molecular weight polyethylene (UHMWPE) is a linear fiber known for its high strength and is used in bulletproof vests for its lightweight and strong impact resistance.

Name the major physiologically active substances that comes from: bark of the willow tree, the pituitary gland, the sap of the poppy and the belladenna plant. a. Cocaine, reserpine, salicin, atropine b. Reserpine, atropine, B-endorphine, opium c. Opium, cocaine, salicin, and reserpine d. Salicin, beta-endomorphin, opium, atropine

d. Salicin, beta-endomorphin, opium, atropine ## Footnote Salicin from willow bark (pain relief) Beta-endorphin from pituitary (pain relief, natural opioid) Opium from poppy sap (painkiller) Atropine from belladonna (used to treat nerve agent exposure)

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. 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 ## Footnote A Nujol mull is made for IR spectroscopy of solids — mineral oil (Nujol) suspends the sample so IR light can pass through.

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 D. c. They are different from electrolytic reactions wherein a movement of a sigma bond with a simultaneous rearrangement of the pi-system does not occur d. They are not the same as the (3, 3) cope arrangement and the beta ring does not undergo photon activated retro electrocyclization

a. They are similar to the (3,3) Cope rearrangement where the beta ring of a steroid undergoes photon activated retro electrocyclization

Org Chem Flashcards

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