Chem Exam 4
Chem Exam 4
Chem Exam 4
ALKANES:
1. Draw the structural and condensed formula of the following hydrocarbon. What is the chemical formula?
2. Draw the structural and condensed formula of the following hydrocarbon. What is the chemical formula?
3. Draw the structural and condensed formula of the following hydrocarbon. What is the chemical formula?
4. Draw the structural and condensed formula of the following hydrocarbon. What is the chemical formula?
5. Draw the structural and condensed formula of the following hydrocarbon. What is the chemical formula?
6. Draw the linear and structural formula of the following hydrocarbon. What is the chemical formula?
7. Draw the linear and structural formula of the following hydrocarbon. What is the chemical formula?
O
CH3 O C CH2 CH3
8. Draw the linear and structural formula of the following hydrocarbon. What is the chemical formula?
9. Draw the linear and structural formula of the following hydrocarbon. What is the chemical formula?
CH3
CH3 CH CH2 CH3
10. Fill in the names/molecular formula, number of carbons and the structures for the first ten alkanes.
Name and Molecular Number of Structure
Formula Carbons
Name Draw
11. Name and draw the substituents that will be used in this class:
Draw
Name
CH2 CH3
CH3 CH2 CH2 CH CH3
13. Draw expanded structural formula for an alkane with three carbon atoms.
19. Using the IUPAC nomenclature system, name the following molecule.
H3C CH3
29. Write the condensed structural formula and draw the expanded structural formula for each of the following.
Propane
Hexane
Heptane
Cyclopentane
32. According to the IUPAC convention for chemical naming, which part of a hydrocarbon is selected as the main chain for a
hydrocarbon chain?
CH 3
CH3 CH CH2 CH2 CH2 CH3
35. What is the IUPAC name of the alkyl group CH3 CH2 CH2?
CH3
CH3 CH CH2 CH2 CH3
37. Alkanes with a branch coming off the straight chain are identified as substituted alkanes. What would be the name of a
straight chain made of 8 carbons with – CH3 groups on the second and fifth carbons?
39. Isomers are molecules that share the same formula and have ________.
40. Indicate whether each of the following pairs represent structural isomers or the same molecule:
and
and
and
41. Draw the condensed structural formula for each of the following alkanes
3,3-dimethylpentane
2,3,5-trimethylhexane
3-ethyl-2-methylheptane
3-ethyl-2,5-dimethyloctane
4-ethyl-2,2-dimethyloctane
1-bromo-2-chloroethane
3-ethylpentane 2-bromopropane
42. Identify the compounds in each of the following pairs as structural isomers or not structural isomers.
and
and
and
and
43. What is the name of a 4-membered carbon ring with a 2-carbon chain branching off the first carbon?
44. Name the haloalkane that has 7 carbons in a chain, a chlorine on the second carbon, and a bromine on the third carbon.
45. What is the structure of isobutane, also known as 2-methylpropane?
46. Draw the condensed structural formula for each of the following cycloalkanes
cyclopropane 1,1-dimethylcyclohexane
cyclobutane 1,3-dimethylcyclohexane
cyclopentane 1,1,2,4-tetraiodocyclopentane
CONFORMATIONS:
1.
Describe at least two specific things that these three structures have in common.
2. Draw and name 3 of the constitutional isomers for C5H12 using the condensed structure and skeletal structure.
3. Draw and name 4 of the constitutional isomers for C6H14 in the condensed formula and line formula.
4. Draw and name 4 of the constitutional isomers for C3H6Br2 in the condensed formula and line formula.
5. Draw and name 4 of the constitutional isomers for C4H9Cl in the condensed formula and line formula.
6. Draw and name 4 of the constitutional isomers for C7H16 in the condensed formula and line formula.
Polar or non-polar?
Line formula:
Dominant intermolecular force:
Isomer #1
C2H6O VE
Polar or non-polar?
Line formula:
Dominant intermolecular force:
8. Draw and name 4 of the constitutional isomers for hexane in the condensed formula and line formula.
9. Draw and name 4 of the constitutional isomers for C4H8F2 in the condensed formula and line formula.
CIS-TRANS ISOMERS (GEOMETRIC ISOMERS)
1. Can 2-methyl-2-butene form cis-trans isomers? Draw the condensed and line formula for the structure(s).
2. Can the following structure from cis-trans isomerism? If so, show how.
1-butene
Can 1-butene form cis-trans isomers?
2-methyl-2-pentene
Can 2-methyl-2-pentene form cis-trans isomers?
2,3-dichloro-2-butene
Can 2,3 dichloro-2-butene form cis-trans isomers?
4. State and name whether the following molecules are cis, trans, or neither.
5. Draw the structure of trans-2-pentene, showing the correct arrangement of atoms around the double bond.
6. Draw the structure of cis-3-heptene, showing the correct arrangement of atoms around the double bond.
cis-2-octene trans-4-decene
trans-3-hexene cis-2-pentene
FUNCTIONAL GROUPS
Alcohol
Carboxylic acid
Ester
Alkene
Phenol
Aromatic Compound
Disulfide
Aldehyde
Ketone
Carbonyl
Carboxylate ion
Amine
Ether
Ammonium ion
Amide
Thiol
Alkyne
Write the product(s) of the following hydration reactions and state whether they are symmetric or asymmetric alkenes.
H+ catalyst
+¿ H2O
H+ catalyst
+¿ H2O
H+ catalyst
+¿ H2O
H+ catalyst
+¿ H2O
H+ catalyst
+¿ H2O
+¿ H2O H+ catalyst
H+ catalyst
+¿ H2O
1. Identify the following molecule as chiral or achiral. If it is chiral, locate and label the chiral carbon(s). If it is not chiral,
explain why.
2. Identify the following molecule as chiral or achiral. If it is chiral, locate and label the chiral carbon(s). If it is not chiral,
explain why.
3. Identify the following molecule as chiral or achiral. If it is chiral, locate and label the chiral carbon(s). If it is not chiral,
explain why.
4. Identify the following molecule as chiral or achiral. If it is chiral, locate and label the chiral carbon(s). If it is not chiral,
explain why.
5. Identify the following molecule as chiral or achiral. If it is chiral, locate and label the chiral carbon(s). If it is not chiral,
explain why.
6. Identify the following molecule as chiral or achiral. If it is chiral, locate and label the chiral carbon(s). If it is not chiral,
explain why.
7. Identify the following molecule as chiral or achiral. If it is chiral, locate and label the chiral carbon(s). If it is not chiral,
explain why.
8. Identify the following molecule as chiral or achiral. If it is chiral, locate and label the chiral carbon(s). If it is not chiral,
explain why.
9. Identify the following molecule as chiral or achiral. If it is chiral, locate and label the chiral carbon(s). If it is not chiral,
explain why.
10. Identify the following molecule as chiral or achiral. If it is chiral, locate and label the chiral carbon(s). If it is not chiral,
explain why.
11. Identify the following molecule as chiral or achiral. If it is chiral, locate and label the chiral carbon(s). If it is not chiral,
explain why.
12. Identify the following molecule as chiral or achiral. If it is chiral, locate and label the chiral carbon(s). If it is not chiral,
explain why.
DEHYDRATION OF AN ALCOHOL
H+ catalyst
Heat
H+ catalyst
Heat
H+ catalyst
Heat
H+ catalyst
Heat
H+ catalyst
Heat
H+ catalyst
Heat
H+ catalyst
Heat
H+ catalyst
Heat
H+ catalyst
Heat
H+ catalyst
Heat
H+ catalyst
Heat
H+ catalyst
Heat
H+ catalyst
Heat
H+ catalyst
Heat
H+ catalyst
Heat
H+ catalyst
Heat
H+ catalyst
Heat
H+ catalyst
Heat
HYDROGENATION REACTION
Ni
Pd cat.
Pt
H2
Pt catalyst
H2
Pt catalyst
H2
Pt catalyst
H2
Pt catalyst
H2
Pt catalyst
H2
Pt catalyst
H2
Pt catalyst
H2
Pt catalyst
H2
Pt catalyst
H2
Pt catalyst
H2
Pt catalyst
H2
Pt catalyst
H2
1. Draw out and explain the equilibrium reaction for carboxylic acid and water.
4. Using structural formulas show how hydrogen bonding can occur between primary, secondary, and tertiary amines.
6. Draw out and explain the equilibrium reaction for an amine and water.
If the above reaction is basic, which side of the reaction is dominating? Why?
If the above reaction is acidic, which side of the reaction is dominating? Why?
What side of the equilibrium is dominating in the body/biological solutions?
8. Fill in the following chart regarding which form these molecule s take in various pH values.
9. What does the formula for an amino acid look like on paper versus in a neutral (biological) solution? Draw it out below.
Carboxylic Acid
Amine
H+ catalyst
+
+ H+ catalyst
+ heat
H+ catalyst
+
+ heat
H+ catalyst
+
heat
H+ catalyst
H+ catalyst
+
+ H+ catalyst
H+ catalyst
+
heat
+
H+ catalyst
H2O
H+ catalyst
H2O
H+ catalyst
H2O
H+ catalyst
H2O
H+ catalyst
H2O
OH-
H2O
heat
H+
H2O
heat
OH-
H2O
heat
H+ catalyst
H2O
H+
H2O
heat
OH-
H2O
heat
OH-
H2O
heat