Download Chapter 21 Worksheet

Chem 1C - CLAS - Chapter 21
1. Classify the following compounds as saturated or
unsaturated.
O
OH
Cl
2. What is the general formula for a hydrocarbon with
one ring and a triple bond?
9. How many compounds can be produced if you mix
chlorine with ethane in the presence of high
energy photons?
10. Predict the product for the following addition
reactions:
a. 1-pentene + Br2 →
b. 2-pentene + HBr →
c. 1-butene + HCl →
11. Which of the following transitions does not
represent a hydrogenation reaction?
a. 1-butene → butane
b. 1-pentyne → pentane
c. pentane → 2-pentene
a. CnH2n+2 b. CnH2n c. CnH2n–2 d. CnH2n–4 e. CnH2n–6
3. Name the following alkanes:
a.
b.
c.
Cl
Br
12. Identify the functional groups that are present in the
following compounds:
Cl
4. Name the following alkenes:
a.
b.
Br
13. For each of the following (1) provide a name (2)
draw the products of oxidation and (3) name the
products:
a.
b.
c.
5. Name the following alkynes:
a.
b.
OH
OH
OH
14. Name the following:
6. Which of the following is not a structural isomer of
2-heptene?
a.
b.
c.
d.
e.
3-heptene
2,4-dimethyl-1-pentene
3-methylcyclohexene
1-methylcyclohexane
2-heptyne
7. Which of the following can have geometric isomers?
a. 2-pentene
b. 2-pentyne
c. cyclopentene
d. 1-pentene
e. 2,3-dimethyl-2-pentene
f. 1,3-dimethylcyclopentane
8. How many dibromobenzenes can you have? Draw
and name them.
a.
O
b.
Br
O
OH
c.
O
H
15. Classify the following amines as primary, secondary
or tertiary
a. tertbutylamine
b. ethylhexylamine
16. Predict and name the products for the following:
a. propanoic acid + 2-methyl-2-propanol →
b. methanoic acid + 2-butanol →
c. hexanoic acid + 2,3-dimethyl-1-pentanol →
17. What compounds would you use to synthesize the
following esters?
a. methyl ethanoate
b. cyclohexyl propanoate
23. Draw the monomer used to make the following
polymers.
a.
b.
c.
18. Circle the chiral carbons in the following:
O
H
H
H
d.
OH
OH
OH
e.
OH
19. Peptide bonds in proteins are the result of
___________ reactions between __________.
What’s the difference between the primary,
secondary and tertiary structure of a protein?
How many possible tripeptides will result if you
were to mix valine, leucine and cysteine
together?
O
O
NH2
Valine
OH
OH
OH
SH
O
NH2
Leucine
NH2
Cysteine
20. What type of monomers are used to make addition
polymers?
a.
b.
c.
d.
Alkanes
Alkenes
Alcohols and carboxylic acids
Amines and carboxylic acids
21. What type of monomers are used to make
condensation polymers?
a. Alkanes
b. Alkenes
c. Alcohols and carboxylic acids
d. Amines and carboxylic acids
22. Draw a short segment of the polymer that is the
result of the following monomers:
a. tetrafluoroethene
b. 4-methyl-2-pentene
c. 1,1-dichloro-1-butene
24. Which of the following are examples of
condensation polymers?
a. Proteins
b. DNA
c. Polysaccharides
d. Polystyrene
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# of H’s = 2(# of C’s) + 2 – 2(# π bonds) – 2 (# of rings) – halogens
Systematic Nomenclature of Organic Compounds
1. Find the longest continuous carbon chain (parent chain).
a. If there is a functional group (double or triple bond, alcohol etc) it must be on or part of the parent chain.
b. If there is a ring in the compound either the ring itself or the non-ringed chain will be the parent chain but
never both combined.
c. If there are two or more chains of equal length, pick the one with the greatest number of substituents.
2. Number the carbons in the parent chain.
a. If there is a functional group, assign it the lowest possible position. If the functional group gets the same
position from either end then consider the lowest number for the substituents. If there is a functional
group on a ring, assign it position 1. Double bonds in a ring are at positions 1 and 2.
b. If there is multiple functional groups the priority is carbonyls > alcohols > carbon-carbon multiple bonds
> amines. If you have a carbon-carbon double bond and a carbon-carbon triple bond, go in the directions
that gives the lowest possible positions. If both directions give the same numbers, the double bond will
take priority.
c. If there are no functional groups, give the substituents the lowest possible numbers. If you get the same
numbers from either end assign the alphabetically first substituent the lowest number.
3. Naming your compound.
a. If the compound has a specific configuration or geometry (cis/trans, E/Z or R/S) indicate this first.
b. The first name is the substituents in alphabetical order. Prefixes that denote a number (di, tri, sec, tert
etc.) are not alphabetized. List the position(s) on the parent chain and denote how many with a Greek
prefix. If a substituent is on a nitrogen the letter N is used to denote the position in lieu of a number.
Hyphens are placed between letters and number whereas commas between two numbers.
c. The last name of the compound is the parent chain. The stem of the name indicates the length of the
parent chain and the suffix reflects the type of compound. If your parent chain is a ring add the prefix
cyclo. If your parent chain had a functional group indicate the position if it’s not obvious.
#C’s
1
2
3
4
5
6
7
8
9
10
Root meth eth prop but pent hex hept oct non dec
Structure
Classification
Systematic suffix
C–C
alkane
ane
C=C
alkene
ene
C≡C
alkyne
yne
C–X
alkyl halide
N/A
C – OH
C–O–C
C–N
alcohol
anol
enol
ynol
anediol
enediol
ynediol
ether
N/A
amine
anamine
enamine
ynamine
Example
pentane
3-hexene
1-butyne
F
2-fluoropentane
OH
cyclopentanol
O
NH2
2-pentanamine
anal
enal
ynal
aldehyde
or RCHO
butanal
O
anone
enone
ynone
ketone
or R(CO)R’
cyclohexanone
O
OH
anoic acid
enoic acid
ynoic acid
carboxylic acid
or RCOOH
or RCOOR’
O
ester
anoate
amide
aka
peptide
anamide
2-propylpentanoic acid
O
O
ethyl pentanoate
O
NH2
2-methylpropanamide
Common substituents or branches
methyl
isopropyl
ethyl
isobutyl
hexyl
propyl
pentyl
sec-butyl
butyl
tert-butyl
Sub-classifications of Alcohols ⇒ count the number of carbons directly bonded to the carbon with the alcohol
tertiary
OH
HO
secondary
OH
primary
Sub-classifications of Amines ⇒ count the number of carbons directly bonded to the nitrogen
H2N primary
N
tertiary
N secondary
H
Chiral or Asymmetrical Carbons ⇒ sp3 carbons bonded to 4 different groups