Question 1

Which of the following is the balanced chemical equation for the catalytic hydrogenation (addition of H2)to CH3CH=CHCH3?

Accepted Answer

A) CH3CH=CHCH3 + 2H2 → 2CH3CH3 
B) CH3CH=CHCH3 + 3H2 → CH3CH3 + 2 CH4 
C) CH3CH=CHCH3 + 2H2 → CH3CH2CH3 + CH4 
D) CH3CH=CHCH3 + H2 → CH3CH2CH2CH3 
E) CH3CH=CHCH3 + 4H2 → 4CH4 
A) CH3CH=CHCH3 + 2H2 → 2CH3CH3 
B) CH3CH=CHCH3 + 3H2 → CH3CH3 + 2 CH4 
C) CH3CH=CHCH3 + 2H2 → CH3CH2CH3 + CH4 
D) CH3CH=CHCH3 + H2 → CH3CH2CH2CH3 
E) CH3CH=CHCH3 + 4H2 → 4CH4

Question 2

Determine the products of the following reaction:   $+\mathrm{HBr} \longrightarrow \text { ? }$

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E) 
  
A) 
  
B) 
  
C) 
  
D) 
  
E)

Question 3

What are primary alcohols oxidized to?

Accepted Answer

A) secondary alcohols 
B) ethers 
C) esters 
D) aldehydes 
E) ketones 
A) secondary alcohols 
B) ethers 
C) esters 
D) aldehydes 
E) ketones

Question 4

Arrange the following in order from least oxidized to most oxidized. I. 
II. 
III. $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { OH }$

Accepted Answer

A) II < I < III 
B) III < I = II 
C) III < I < II 
D) I < II < III 
E) I < III < II 
A) II < I < III 
B) III < I = II 
C) III < I < II 
D) I < II < III 
E) I < III < II

Question 5

Write chemical formulas for the missing products in the following reaction.
CH3COOH + (COCl)2 → CH3COCl + HCl + ? + ?

Accepted Answer

Question 6

What is a hemiketal?

Accepted Answer

A) A hemiketal,prepared from an alcohol and an aldehyde,is a compound that contains both OH and OR groups on the same carbon. 
B) Compounds prepared from ketones and alcohols and with OH and OR groups on the same carbon are known as hemiketals. 
C) A hemiketal is a product of acetyl group hydrolysis; it contains a COOH functional group. 
D) A hemiketal is formed from alcohols and acetic acid; a hemiacetal has both acetyl and OH groups on the same carbon atom. 
E) A hemiketal,formed from a ketone and an alcohol,has OH and keto groups on adjacent carbon atoms in its structure. 
A) A hemiketal,prepared from an alcohol and an aldehyde,is a compound that contains both OH and OR groups on the same carbon. 
B) Compounds prepared from ketones and alcohols and with OH and OR groups on the same carbon are known as hemiketals. 
C) A hemiketal is a product of acetyl group hydrolysis; it contains a COOH functional group. 
D) A hemiketal is formed from alcohols and acetic acid; a hemiacetal has both acetyl and OH groups on the same carbon atom. 
E) A hemiketal,formed from a ketone and an alcohol,has OH and keto groups on adjacent carbon atoms in its structure.

Question 7

Determine the product(s)of the following reaction:   $\stackrel { \mathrm { NaCN } } { \longrightarrow }$ ?

Accepted Answer

A) 
  
B) 
  
C) 
$$\mathrm { CH } _ { 3 } - \mathrm { CH } = \mathrm { CH } - \mathrm { CH } _ { 3 }$$ 
D) 
  
E) 
  
A) 
  
B) 
  
C) 
$$\mathrm { CH } _ { 3 } - \mathrm { CH } = \mathrm { CH } - \mathrm { CH } _ { 3 }$$ 
D) 
  
E)

Question 8

Which of the following is the balanced chemical equation for the addition of HBr to CH2=CHCH2CH3?

Accepted Answer

A) CH2=CHCH2CH3 + HBr → CH2BrCH2CH2CH3 
B) CH2=CHCH2CH3 + 2HBr → 2CH2BrCH3 
C) CH2=CHCH2CH3 + 2HBr → CH3Br + CH2BrCH2CH3 
D) CH2=CHCH2CH3 + 4HBr → 4CH3Br 
E) CH2=CHCH2CH3 + HBr → CH3CHBrCH2CH3 
A) CH2=CHCH2CH3 + HBr → CH2BrCH2CH2CH3 
B) CH2=CHCH2CH3 + 2HBr → 2CH2BrCH3 
C) CH2=CHCH2CH3 + 2HBr → CH3Br + CH2BrCH2CH3 
D) CH2=CHCH2CH3 + 4HBr → 4CH3Br 
E) CH2=CHCH2CH3 + HBr → CH3CHBrCH2CH3

Question 9

What is the product obtained after a reaction between an aldehyde and Grignard reagent is worked-up with dilute acid?

Accepted Answer

A) a ketone 
B) a primary alcohol 
C) a secondary alcohol 
D) a tertiary alcohol 
E) a carboxylic acid 
A) a ketone 
B) a primary alcohol 
C) a secondary alcohol 
D) a tertiary alcohol 
E) a carboxylic acid

Question 10

Identify the most oxidized compound.

Accepted Answer

A) CH3CH2COOH 
B) CH3CH2CHO 
C) CH3CH2CH3 
D) CH3CH2OCH3 
E) CH3CH2CH2OH 
A) CH3CH2COOH 
B) CH3CH2CHO 
C) CH3CH2CH3 
D) CH3CH2OCH3 
E) CH3CH2CH2OH

Question 11

What type of polymers are polyamides?

Accepted Answer

A) Polyamides,formed via step-growth polymerization of diacids and diamines,have the monomers connected through hydrogen bonds. 
B) Polyamides,formed via step-growth polymerization of diacids and diamines,have the monomers connected through amine bonds. 
C) Polyamides,formed via addition polymerization of diacids and diamines,have the monomers connected through amide bonds. 
D) Polyamides,formed via step-growth polymerization of acids and amines,have the monomers connected through amide groups. 
E) Polyamides,formed via step-growth polymerization of diacids and diamines,have the monomers connected through amide groups. 
A) Polyamides,formed via step-growth polymerization of diacids and diamines,have the monomers connected through hydrogen bonds. 
B) Polyamides,formed via step-growth polymerization of diacids and diamines,have the monomers connected through amine bonds. 
C) Polyamides,formed via addition polymerization of diacids and diamines,have the monomers connected through amide bonds. 
D) Polyamides,formed via step-growth polymerization of acids and amines,have the monomers connected through amide groups. 
E) Polyamides,formed via step-growth polymerization of diacids and diamines,have the monomers connected through amide groups.

Question 12

Draw a clear mechanism for the formation of a hemiacetal from CH3CH2CHO and methanol under acidic conditions.Make sure to indicate each step of the mechanism (if there is more than one)as well as to use arrows to show the electron flow.

Accepted Answer

The formation of a hemiacetal from CHCHC

Question 13

Which combination of reagents would you use to brominate an aromatic compound?

Accepted Answer

A) Br2 and FeCl3 
B) HBr and H2SO4 
C) Br2 and FeBr3 
D) HBrO and FeBr3 
E) HBr and HNO3 
A) Br2 and FeCl3 
B) HBr and H2SO4 
C) Br2 and FeBr3 
D) HBrO and FeBr3 
E) HBr and HNO3

Question 14

Which combination of reagents is used in the Friedel-Crafts alkylation?

Accepted Answer

A) alkyl chloride,R-Cl,and aluminum hydroxide,Al(OH)3 
B) alkyl chloride,R-Cl,and aluminum fluoride,AlF3 
C) alkyl chloride,R-Cl,and aluminum chloride,AlCl3 
D) alkyl chloride,R-Cl,and aluminum oxide,Al2O3 
E) acyl chloride,RC(=O)Cl,and aluminum chloride,AlCl3 
A) alkyl chloride,R-Cl,and aluminum hydroxide,Al(OH)3 
B) alkyl chloride,R-Cl,and aluminum fluoride,AlF3 
C) alkyl chloride,R-Cl,and aluminum chloride,AlCl3 
D) alkyl chloride,R-Cl,and aluminum oxide,Al2O3 
E) acyl chloride,RC(=O)Cl,and aluminum chloride,AlCl3

Question 15

Find the suitable reagent for the transformation:

Accepted Answer

A) CrO3,H3O+ 
B) pyridinium chlorochromate (PC
C)  
C) K2Cr2O7,H2SO4 
D) KMnO4,H2SO4 
E) K2Cr2O7,HNO3 
A) CrO3,H3O+ 
B) pyridinium chlorochromate (PC
C)  
C) K2Cr2O7,H2SO4 
D) KMnO4,H2SO4 
E) K2Cr2O7,HNO3

Question 16

Which pair of compounds would react to produce a polymer?

Accepted Answer

A) an acid and a diol 
B) a diacid and an alcohol 
C) a diacid and a diol 
D) an alcohol and an acid 
E) a diacid and a diketone 
A) an acid and a diol 
B) a diacid and an alcohol 
C) a diacid and a diol 
D) an alcohol and an acid 
E) a diacid and a diketone

Question 17

Which of the following statements is TRUE?

Accepted Answer

A) H-X molecules add across C=C bonds with retention of absolute configuration. 
B) The addition of H-X molecules to alkenes and alkynes is a one-step mechanism. 
C) The rate of H-X addition depends strongly on the nature of the leaving group. 
D) According to Markovnikov's rule,the hydrogen cation adds to the C=C bond in such a way as to generate the most stable carbocation. 
E) The hydrogen cation adds to the more substituted carbon atom of the C=C bond,a fact known as the Markovnikov's rule. 
A) H-X molecules add across C=C bonds with retention of absolute configuration. 
B) The addition of H-X molecules to alkenes and alkynes is a one-step mechanism. 
C) The rate of H-X addition depends strongly on the nature of the leaving group. 
D) According to Markovnikov's rule,the hydrogen cation adds to the C=C bond in such a way as to generate the most stable carbocation. 
E) The hydrogen cation adds to the more substituted carbon atom of the C=C bond,a fact known as the Markovnikov's rule.

Question 18

Give the product of the oxidation of the following compound:

Accepted Answer

A) CH3CH2CHO 
B) CH3CH2CH2OH 
C) CH3CH2CH3 
D) CH3CH2COOH 
E) CH3CH2OCH3 
A) CH3CH2CHO 
B) CH3CH2CH2OH 
C) CH3CH2CH3 
D) CH3CH2COOH 
E) CH3CH2OCH3

Question 19

Which of the following statements is TRUE?

Accepted Answer

A) The slow step in an SN1 mechanism is the dissociation step,which produces a carbanion and a leaving group. 
B) In an SN1 mechanism,during the second step the nucleophile attacks the carbocation formed in the first step. 
C) Primary alkylhalides are the best substrates for SN1 reactions. 
D) The hydroxyl (OH-)group is an excellent leaving group in SN1 reactions. 
E) In an SN1 mechanism,during the second step the nucleophile attacks the carbanion formed in the first step. 
A) The slow step in an SN1 mechanism is the dissociation step,which produces a carbanion and a leaving group. 
B) In an SN1 mechanism,during the second step the nucleophile attacks the carbocation formed in the first step. 
C) Primary alkylhalides are the best substrates for SN1 reactions. 
D) The hydroxyl (OH-)group is an excellent leaving group in SN1 reactions. 
E) In an SN1 mechanism,during the second step the nucleophile attacks the carbanion formed in the first step.

Question 20

Choose the weak acid from the compounds below.

Accepted Answer

A) CH3CH2NH2 
B) CH3CH2CO2H 
C) CH3CH2OCH3 
D) CH3CH2F 
E) CH3COOC2H5 
A) CH3CH2NH2 
B) CH3CH2CO2H 
C) CH3CH2OCH3 
D) CH3CH2F 
E) CH3COOC2H5

Exam 21: Organic Chemistry II: Reactions

Which of the following is the balanced chemical equation for the catalytic hydrogenation (addition of H2)to CH3CH=CHCH3?

Determine the products of the following reaction: +HBr⟶ ? +\mathrm{HBr} \longrightarrow \text { ? }+HBr⟶ ?

What are primary alcohols oxidized to?

Arrange the following in order from least oxidized to most oxidized. I. II. III. CH3CH2CH2−OH\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { OH }CH3​CH2​CH2​−OH

Write chemical formulas for the missing products in the following reaction. CH3COOH + (COCl)2 → CH3COCl + HCl + ? + ?

What is a hemiketal?

Determine the product(s)of the following reaction: ⟶NaCN\stackrel { \mathrm { NaCN } } { \longrightarrow }⟶NaCN​ ?

Which of the following is the balanced chemical equation for the addition of HBr to CH2=CHCH2CH3?

What is the product obtained after a reaction between an aldehyde and Grignard reagent is worked-up with dilute acid?

Identify the most oxidized compound.

What type of polymers are polyamides?

Draw a clear mechanism for the formation of a hemiacetal from CH3CH2CHO and methanol under acidic conditions.Make sure to indicate each step of the mechanism (if there is more than one)as well as to use arrows to show the electron flow.

Which combination of reagents would you use to brominate an aromatic compound?

Which combination of reagents is used in the Friedel-Crafts alkylation?

Find the suitable reagent for the transformation:

Which pair of compounds would react to produce a polymer?

Which of the following statements is TRUE?

Give the product of the oxidation of the following compound:

Which of the following statements is TRUE?

Choose the weak acid from the compounds below.

Units of Measurement for Physical and Chemical Change

Atoms and Elements

Molecules,compounds,and Nomenclature

Chemical Reactions and Stoichiometry

Gases

Thermochemistry

The Quantum-Mechanical Model of the Atom

Periodic Properties of the Elements

Chemical Bonding I: Lewis Theory

Chemical Bonding II: Molecular Shapes, valence Bond Theory, and Molecular Orbital Theory

Liquids, solids, and Intermolecular Forces

Solutions

Chemical Kinetics

Chemical Equilibrium

Acids and Bases

Aqueous Ionic Equilibrium

Gibbs Energy and Thermodynamics

Electrochemistry

Radioactivity and Nuclear Chemistry

Organic Chemistry I: Structures

Biochemistry

Chemistry of the Nonmetals

Metals and Metallurgy

Transition Metals and Coordination Compounds

Filters

Which of the following is the balanced chemical equation for the catalytic hydrogenation (addition of H₂)to CH₃CH=CHCH₃?

Determine the products of the following reaction: $Determine the products of the following reaction: +\mathrm{HBr} \longrightarrow \text { ? }$ $+\mathrm{HBr} \longrightarrow \text { ? }$

Write chemical formulas for the missing products in the following reaction. CH₃COOH + (COCl)₂ → CH₃COCl + HCl + ? + ?

Determine the product(s)of the following reaction: $Determine the product(s)of the following reaction: \stackrel { \mathrm { NaCN } } { \longrightarrow } ?$ $\stackrel { \mathrm { NaCN } } { \longrightarrow }$ ?

Which of the following is the balanced chemical equation for the addition of HBr to CH₂=CHCH₂CH₃?

Draw a clear mechanism for the formation of a hemiacetal from CH₃CH₂CHO and methanol under acidic conditions.Make sure to indicate each step of the mechanism (if there is more than one)as well as to use arrows to show the electron flow.