Chapter 19 – Review

19.1 – 19.5 Alkanes, Alkenes, Alkynes and Aromatic Hydrocarbons; Alcohols and Ethers; Aldehydes, Ketones, Carboxylic Acids and Esters; Amines and Amides; and Families of Organic Molecules – Functional Groups

  1. Classify each compound as organic or inorganic. Check answers[1]
    1. C3H8O
    2. CaCl2 
    3. Cr(NH3)3Cl3 
    4. C30H48O3N
  2. Which compound is likely organic and which is likely inorganic? Check answers[2]
    1. a flammable compound that boils at 80°C and is insoluble in water
    2. a compound that does not burn, melts at 630°C, and is soluble in water
  3. Classify each compound as organic or inorganic. Check answers[3]
    1. C6H10 
    2. CoCl2
    3. C12H22O11 
  4. Classify each compound as organic or inorganic.
    1. CH3NH2
    2. NaNH2
    3. Cu(NH3)6Cl2
  5. Which member of each pair has a higher melting point? Check answers[4]
    1. CH3OH and NaOH
    2. CH3Cl and KCl
  6. Which member of each pair has a higher melting point?
    1. C2H6 and CoCl2
    2. CH4 and LiH
  7. Locate and identify the functional groups in the following molecules.
A benzene ring with C H 2 O H group on the C 1 and N H C H 3 group on the C 2 carbon is represented.
(Credit: Organic Chemistry (OpenStax), CC BY-NC-SA 4.0).

(b)

A six membered ring with a double bond and a carbonyl group is represented.
(Credit: Organic Chemistry (OpenStax), CC BY-NC-SA 4.0).

(c)

A benzene ring linked to an N H group linked to a C O C H 3 group is represented.
(Credit: Organic Chemistry (OpenStax), CC BY-NC-SA 4.0).

(d)

A C H 3 group linked to a C H connected to an amine group is shown. The C H is connected to a C O O H group.
(Credit: Organic Chemistry (OpenStax), CC BY-NC-SA 4.0).

(e)

Two six membered rings fused together is shown. Both the rings have double bond, carbonyl group and a C H 3 group.
(Credit: Organic Chemistry (OpenStax), CC BY-NC-SA 4.0).

(f)

Two C H 3 groups linked to a triple bond linked to a carbonyl linked to a chlorine group.
(Credit: Organic Chemistry (OpenStax), CC BY-NC-SA 4.0).

19.6 General Reactions of Carbon

  1. Classify each of the following reactions as an addition, elimination, substitution, or rearrangement: Check answers[5]
    1. 1. CH3Br + KOH ⟶ 
    2. 2. CH3CH2Br ⟶ 
    3. 3. H2C=CH2 + H2 ⟶ 
  2. Identify the nucleophile and the electrophile in the nucleophilic substitution reaction of 2-bromobutane with KCN. Check answer [6]
  3. Identify the nucleophile and the electrophile in the nucleophilic substitution reaction of 1-chloropentane with sodium methoxide.
  4. Do you expect an elimination reaction to be favoured by a strong or a weak base? Why?
  5. Why do molecules with π bonds behave as nucleophiles when mixed with strong electrophiles?
  6. Sketch the mechanism for the nucleophilic substitution reaction of potassium cyanide with iodoethane.
  7. Sketch the mechanism for the nucleophilic substitution reaction of NaSH with 1-bromopropane.
  8. Sketch the mechanism for the elimination reaction of cyclohexylchloride with potassium ethoxide. Identify the electrophile and the nucleophile in this reaction.
  9. What is the product of the elimination reaction of 1-bromo-2-methylpropane with sodium ethoxide?
  10. Write the structure of the product expected from the electrophilic addition of HBr to cis-3-hexene.
  11. Write the structure of the product expected from the electrophilic addition of 1-methylcyclopentene to HBr. Identify the electrophile and the nucleophile, and then write a mechanism for this reaction.
  12. Write a synthetic scheme for making propene from propane. After synthesizing propene, how would you make 2-bromopropane?
  13. Write a synthetic scheme for making ethylene from ethane. After synthesizing ethylene, how would you make iodoethane?
  14. From the high-temperature reaction of Br2 with 3-methylpentane, how many monobrominated isomers would you expect to be produced? Which isomer is produced from the most stable radical? Check answer [7]
  15. For the photochemical reaction of Cl2 with 2,4-dimethylpentane, how many different monochlorinated isomers would you expect to be produced? Which isomer is produced from the most stable precursor radical?
  16. How many different radicals can be formed from the photochemical reaction of Cl2 with 3,3,4-trimethylhexane? Check answer [8]
  17. How many monobrominated isomers would you expect from the photochemical reaction of Br2 with
    1. isobutene?
    2. 2,2,3-trimethylpentane?
  18. Arrange acetone, ethane, carbon dioxide, acetaldehyde, and ethanol in order of increasing oxidation state of carbon.
  19. What product(s) do you expect from the reduction of a ketone? the oxidation of an aldehyde?
  20. What product(s) do you expect from the reduction of formaldehyde? the oxidation of ethanol? Check answer [9]

Links to Enhanced Learning

Samantha Sullivan-Sauer’s H5P Matching Organic Chemistry Functional Groups.

Khan Academy reviews Identifying Functional Groups [New tab].

Science Geek reviews Organic Functional Groups [New tab]

Create your own organic nomenclature quiz to identify functional groups using Organic Nomenclature [New tab].  You can customize the types of questions you receive and get instant feedback.

Attribution & References

Except where otherwise noted, this page is adapted by Adrienne Richards from:

  1. a) organic b) inorganic c) inorganic d) organic ↵
  2. a) organic b) inorganic ↵
  3. a) organic b) inorganic c) organic ↵
  4. a) NaOH b) KCl ↵
  5. a) CH3OH + KBr b) H2C=CH2 + KBr c) CH3CH3 ↵
  6. CN− is the nucleophile, and C2H5Cδ+HBrCH3 is the electrophile. ↵
  7. four; 3-bromo-3-methylpentane ↵
  8. seven ↵
  9. methanol; acetaldehyde, followed by acetic acid and finally CO2 ↵

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Organic and Biochemistry Supplement to Enhanced Introductory College Chemistry Copyright © 2024 by Gregory Anderson; Caryn Fahey; Adrienne Richards; Samantha Sullivan Sauer; David Wegman; and Jen Booth is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License, except where otherwise noted.

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