This document provides practice problems for organic chemistry students. It includes questions on drawing and naming alkanes, alkenes, alkynes, cycloalkanes and their derivatives. There are also questions on identifying structural and geometric isomers, aromatic hydrocarbons, alcohols, aldehydes, ketones, carboxylic acids and esters. Students are asked to draw structural diagrams, provide systematic names, identify isomers and resonance structures, and write formulas from names. The document covers a wide range of fundamental organic chemistry concepts and reaction types.
This document provides practice problems for organic chemistry students. It includes questions on drawing and naming alkanes, alkenes, alkynes, cycloalkanes and their derivatives. There are also questions on identifying structural and geometric isomers, aromatic hydrocarbons, alcohols, aldehydes, ketones, carboxylic acids and esters. Students are asked to draw structural diagrams, provide systematic names, identify isomers and resonance structures, and write formulas from names. The document covers a wide range of fundamental organic chemistry concepts and reaction types.
This document provides practice problems for organic chemistry students. It includes questions on drawing and naming alkanes, alkenes, alkynes, cycloalkanes and their derivatives. There are also questions on identifying structural and geometric isomers, aromatic hydrocarbons, alcohols, aldehydes, ketones, carboxylic acids and esters. Students are asked to draw structural diagrams, provide systematic names, identify isomers and resonance structures, and write formulas from names. The document covers a wide range of fundamental organic chemistry concepts and reaction types.
This document provides practice problems for organic chemistry students. It includes questions on drawing and naming alkanes, alkenes, alkynes, cycloalkanes and their derivatives. There are also questions on identifying structural and geometric isomers, aromatic hydrocarbons, alcohols, aldehydes, ketones, carboxylic acids and esters. Students are asked to draw structural diagrams, provide systematic names, identify isomers and resonance structures, and write formulas from names. The document covers a wide range of fundamental organic chemistry concepts and reaction types.
You can print a copy of every organic sheet. For each drawing question you must write down the name, draw the structural diagram and number the carbons and circle the branches. For each naming question you must copy the drawing, number the drawing and write the name.
1. Draw and name two structural isomers of hexane that have a single methyl group. 2. Draw and name four structural isomers that have two methyl groups attached to pentane. 3. Draw and name all the isomers of octane. 4. Draw and name all the isomers of chloropentane. 5. Draw and name all the isomers of dichloropentane that have two methyl groups. 6. Draw and name three structural isomers of 3-methylpent-1-yne. No rings can be used.
B. Geometrical isomer questions
1. Draw the following structures. a. cis-hex-2-ene b. hex-2-yne c. cis-4-methyloct-2-ene d. trans-2,2-dimethyldec-4-ene e. but-1-yne f. trans-4-methylhept-2-ene
2. Which of the following can exhibit geometrical isomerism? a. pent-1-ene b. 2-methylhex-3-ene c. 2-methylpent-2-ene d. non-4-yne e. 1-chloroprop-1-ene f. 3-ethyldec-3-ene g. cyclobutane h. 2,3-dibromopent-2-ene
Organic Chemistry 2010 Baverstock/Kailley Page 8
3. Name the following:
a. C H 3 CH 3 H H
h. C H 3 CH 3 H H
b. CH 3 Cl Cl Cl
i. C H 3 CH 3 H H
c. CH 3 H H F
j. CH 3 C H 3 CH 3 CH 3 C H 3
d. C H 3 CH 3 H H
k. C H 3 Cl Cl CH 3 C H 3
e. C H 3 CH 3 CH 3 H
l. C H 3 CH 3 H H
f. F F CH 3 CH 3
m. Br Br Cl F
g. Br Br H Br
n. C H 3 C H 3 CH 3 CH 3
4. Draw the following. (use bow-tie structures around the double bond as above)
a. cis-pent-2-ene b. trans-non-3-ene c. cis-1,3-difluorobut-1-ene d. trans-4,5-dichloronon-4-ene e. propene f. cis-4,4-dimethylpent-2-ene g. trans-2,3-dibromobut-2-ene Organic Chemistry 2010 Baverstock/Kailley Page 9
h. cis-1-fluoro-4,5-dimethylhex-2-ene i. 1,1-diiodobut-1-ene j. 2,3-dichlorobuta-1,3-diene
C. Aromatic hydrocarbons questions
1. Draw all of the resonance structures of 1,4-dichlorobenzene. 2. Draw all of the structural isomers of 1,4-dichlorobenzene. 3. What is the difference between resonance structures and structural isomers? 4. Below is a picture of naphthalene. Draw all of the resonance structures of naphthalene.
5. Below is a picture of anthracene. Draw all the resonance structures of anthracene.
6. Below is a picture of phenanthrene. Draw all the resonance structures of phenanthrene.
7. Name the following: a. C H 3
b. CH 3 CH 3 Cl
c. CH 3 CH 3 CH 3 CH 3 C H 3 C H 3
d. Br Br Br Br
e. CH 3 CH 3 C H 3
f. Br Br
8. Draw the following: a. cyclobutylbenzene b. 1,2-dipropylbenzene c. 1,4-dichloro-2-ethylbenzene d. bromobenzene e. 1-fluoro-2-propylbenzene f. 1,2,4-trimethylbenzene
1. Draw and name all the isomers for C 5 H 11 CHO. 2. Draw and name all the isomers for C 4 H 9 OH. 3. Draw and name all the isomers for a ketone with 5 carbons, 1 oxygen and 8 hydrogen.
D. Write the name or formula for the following aldehydes and alcohols. 1. C 2 H 5 OH 2. C 3 H 7 CHO 3. C 5 H 9 OH 4. C 8 H 15 CHO 5. C 4 H 7 CHO 6. 2-methylpropan-1-ol 7. octanal 8. 2,2-dimethylheptan-3-ol 9. but-1-en-2-ol 10. pent-3-enal 11. pent-4-yn-2-ol 12. 2-ethylhex-5-ynal
D. For each reaction draw structural diagrams for all of the organic based compounds and write formulas for the simple ionic and covalent compounds. Name the products.
E. Draw all of the organic structures. Write the formula for the inorganic substances. Name the reactants and/or products.
1. 3,4-dimethylhexanoic acid + potassium hydroxide 2. sodium 2-ethylpentanoate + water 3. Trans-pent-3-enoic acid + water 4. hept-5-ynoate + hydronium ion 5. butan-1-ol + 2,3-dichlorohexanoic acid 6. propyl trans-2,3-dihydroxyprop-2-enoate + water 7. butan-2-ol + ethanoic acid
F. Combustion Reactions
1. What are the products of a hydrocarbon combustion reaction?
2. Write the balanced reactions for the combustion reactions. Write everything as formulas! Balanced reactions must have the simplest whole number coefficients (no fractions). Do not write one as a coefficient.
a. propane is burned (means combustion or reacts with oxygen) b. hexane is burned c. cyclobutane is burned d. ethanol is burned e. pentanal is burned
Organic Chemistry Review
1. Why does carbon make-up the backbone of all organic compounds?
2. Which organic compounds are saturated? Unsaturated?
3. Name properties of the following:
a. alkanes b. alkenes c. alcohols d. carboxylic acids e. amines f. ethers g. esters h. benzenes Organic Chemistry 2010 Baverstock/Kailley Page 18
4. Write molecular formulas for the following:
a. 3-methyloctane b. methylcyclopentane c. 1,2-dichlorohexane d. propan-1-ol e. butanoic acid f. 3-ethylhept-1-ene g. cyclobutyne h. 3-propylcyclononene
5. Draw and name an example of an organic:
a. acid b. base c. beverage alcohol
6. Which of the following are miscible in water? a. alkanes b. alcohols c. benzenes d. carboxylic acids e. amines
7. Which is more reactive? a. alkanes or alkenes b. alkanes or alcohols c. ketones or carboxylic acid
8. For each reaction draw structural diagrams for all of the organic based compounds and write formulas for the simple ionic and covalent compounds. Name the products.
a. hexanoic acid + potassium hydroxide b. propanoic acid + water c. heptan-3-amine + hydrochloric acid d. ethanamine + water e. butanoic acid + propan-1-amine f. butan-1-ol + heptanoic acid g. decan-1-ol + 2,3-dimethylpent-4-enoic acid h. propane + oxygen
9. Draw and name one set of geometrical isomers for C 4 H 8 .
10. Draw and name all the structural isomers for C 5 H 8 .
11. Draw the following:
a. 2,2,4-trimethylpentane b. trans-hex-3-ene c. 4,4-dimethylpent-2-yne d. 1,1-dibromo-3-chlorobut-1-ene e. 2,4-dimethyl-1,3,5-trinitrobenzene f. butane-1,2-diol g. pent-3-yn-2-one Organic Chemistry 2010 Baverstock/Kailley Page 19
h. but-3-enoic acid i. 2,3,4-trimethylpentanal j. 2,2-dimethylheptan-3-one k. ethyl cis-2-fluoropent-3-enoate l. N-ethyl-N,4,4-trimethylocta-5,7-diynamide m. 3-ethylpentane-1,2-diamine n. butyl cis-2,2-dimethylhex-3-enoate