MASTERING ORGANIC CHEMISTRY
By-- S.K.SINHA
1
The IUPAC Systematic Approach to Nomenclature •
Identify Identify Root:-Find Root:-Find the parent hydrocarbon. This is based on the longest continuous carbon chain. If there are chains of equivalent length, then select the one with the most branch points as the parent.
Number the chain:-Number chain :-Number the atoms in the parent chain, beginning at the end nearer the first branch point. If there is branching an equal distance from both ends, then consider the next branch point. Identify the substituents:substituents :- Identify and number the substituents. Remember there must be as many numbers as there as substitutents. Writing the name:- Write out the name as a single word, using hyphens to separate the different prefixes and commas to separate the numbers. If two or more different substitutents are present, cite them in alphabetical order. With identical substituents, use the prefix di-, tri-, tetra- etc. etc . as required. Ignore these prefixes when alphabetising. If a substituent has subranching (ie. its complex) then reapply the first 4 steps as if it were a compound. Numbering must begin at the point of attachment. Now set this substituent in parentheses. Naming Naming the parent chain: Here chain: Here is a list of the root names for the hydrocarbon chains •
•
•
•
C1 = meth- C2 = ethoctC9 = non-
C3 = propC10 = dec-
C4 = butC5 = pentC6 = hex- C7 = heptC8 = C11 = undec- C12 = dodec- C18 = octadec- C20 = icos-
IUPAC Rules for Naming Organic Molecules To name a compound using the IUPAC system, follow the steps shown (if applicable) in the following order. Step 1 Determine the principle functional functional group in the compound. When a compound contains more than one group in Table 1, the principle group is that which has the highest precedence. This group will be cited as a suffix; all other groups are cited as prefixes. Functional Group a -(C) OOH -COOH -SO2OH -C(O)OC(O)-(C)OOR -COOR -(C)OX -COX -(C)ONH 2 -CONH2 -(C)≡N -C≡N -(C)HO -CHO >(C)=O -OH -SH -NH2 >NH >C=C< -C≡C-X, -R, -OR -Ar, -NO2 -NO, -N3 =N2, -SR a
Suffix if Highest Precedence -oic acid -carboxylic acid -sulfonic acid -oic anhydride alkyl -oate alkyl carboxylate -oyl halide -carbonyl halide -amide -carboxamide -nitrile -carbonitrile -al -carbaldehyde -one -ol -thiol -azane (-amine) -azane (-imine) -ene -yne -
Prefix Prefix if Lower Prededence carboxysulfoalkoxy-oxohalo-oxohalocarbonylamino-oxoaminocarbonylcyanooxoformyloxohydroxysulfanylazanyl- (-amino) azanylidene* ** halo-, alky-l, alkoxyaryl-, nitronitroso-, azidodiazo-, (R (R)-sulfanyl-
(C) designates a carbon atom included in the parent hydrocarbon (part of the longest chain or ring.
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MASTERING ORGANIC CHEMISTRY
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* and ** These are always used as a suffix. If a higher priority group is present in the molecule the suffix is changed to –en– or –yn– an d is followed by the suffix of the higher priority group. Step 2 Determine the parent hydrocarbon (principle chain or ring system system): (a) If the principle group occurs in a chain, the principle chain is selected as (i) the chain containing the functional group of the highest seniority as the parent. OH
2-(propan-1-yl)pentan-1-ol (ii) If more than one such choice is possible, select the chain with the maximum number of multiple bonds.
2-(hexan-1-yl)buta-1,3-diene (iii) If (i) and (ii) together are not definitive, then choose the longest chain. (iv) If two chains of the same length are possible, choose the one with the maximum number of substituent groups. O
H
2-(butan-1-yl)-4-methylhexanal The parent chain here contains six carbon atoms. If the principle functional group occurs in a cyclic system, that cyclic system forms the parent.
(b)
OH
2-(octan-1-yl)cyclohexanol
2-(hexan-1-yl)cyclopentene
Step 3 Name the parent structure of and the principle group(s). Give the parent name the same name as if it were an alkane, but replace –ane with the suffix characteristic of the functional group of the highest priority (Table 1). Note: Multiple unsaturation in hydrocarbons is indicated by the numerical prefixes di-, tri-, etc. In such cases, however, the ending –ane of the parent alkane is replaced with –adiene, –atriene, etc. leaving the “a” in the root alkane name whenever the first letter of the suffix is a consonant to make the name easier to pronounce. Thus we get alkadienes, alkatrienes, alkadiynes, etc. Step 4 Complete the number system. (a) Number the carbon atoms consecutively from the end of the chain nearer the functional group of the highest priority. 1
2
3
5
4,5-dimethylhexan-3-one
6
4 O
(b) 1
If the same number for the functional group of highest priority is obtained in both directions, the correct IUPAC name is the one that contains the lowest substituent numbers.
(d)
2,4-dimethylhex-3-ene
5
3
(c)
6
4
2
The substituent numbers are 2 and 4. If we numbered from the other end, the substituent numbers would have been 3 and 5. 2+4 is a lower numbering system than 3+5. If the first substituents occur at an equal didtance from each end of the chain, number the end nearer a second substituent. If still the same, continue until the first point of difference. If numbering for either end gives the same set of numbers, number from the end with the substituent that comes first in alphabetical order. 6 2
5
3
1
2-chloro-5-methylhex-3-ene
4 Cl
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In monosubstituted cycloalkanes and benzene derivatives. The carbon to which the substituent is bonded is always number 1. If there is only one substituent, the locant number “1” is omitted. However, the number one is required in polysubstituted compounds. NO 2
CH3
OH I
Cl
(f)
Br
Cyclopentanol 1-chloro-2-methylcyclohexane 2-bromo-4-iodo-1-nitrobenzene In polysubstituted cyclic compounds, the starting point and the direction of numbering are chosen to give the lowest numbering system. The starting point is chosen according to the following factors: (i) The principle functional group named as the suffix is always given the lowest possible number. Because certain cyclic systems have fixed numbering systems, it is not always possible to place a substituent on carbon number 1. 6
4
HO
NO 2 5
1
Br
3
OH 7
2
2
6
4
2
1
8
CH3
5
N
3
6
1
3
5 4 IUPAC: 3-nitrobenzen-1-ol 3-methylazabenzene 7-bromonaphthalene-2-ol (3-nitrophenol accepted) (3-methylpyridine accepted ) (7-bromo-2-naphthol accepted) Note: When one heteroatom is present in the ring the number 1 is assigned to that atom. If more than one is present then we use the number 1 on the O, S, or N in that order of priority.
3
4
4
4
3
N 3
5 N
2
S 2
5
5
6
2 N
O
O 1
1
1
IUPAC: oxole(Furan accepted) 1,2-oxathiolane (ii) Lowest numbering for multiple bonds in cyclic compounds. 4
1,3,5-triazine
2
Cl
OH
CH3 5
3
6
2
3
1 6
4
CH3
1
5
5-chloro-3-methylcyclohexene 6-methylcyclohex-3-en-1-ol Note: In naming cycloalkenes, the double bond is located between C1 and C2, and the “1” is usually omitted in the name. The ring is numbered clockwise or counterclockwise to give the first substituent the lower number. However, when functional group with a higher priority than an alkene is present, the carbon bonded to the higher priority group becomes C1 and then multiple bonds are considered for lowest possible numbering. (iii) Lowest numbering for first substituent (or first point of difference). Cl 3
4 5
6
CH2CH2CH3
CH3 5
2
4
1 OH
6 1 3
2
Cl
CH3
4-chloro-2-methylcyclohexan-1-ol 4-chloro-2-methyl-1-(propan-1-yl)cyclohexane (iv) If the same numbers will result from numbering in either direction, give the lowest number for the substituent that is cited first in the name. 4
Br CH3 3 2
4 5
CH2CH3 1
Cl
3 6
2 1 O
2-ethyl-3-methylnaphthalene 3-bromo-5-chlorocyclohexanone Step 5 Name alkyl groups, halides, and other substituents and determine their position on the chain by the numbering system established by step 4. Step 6 Assign the stereochemistry to chiral carbon atoms (stereocenters) and the double bond(s): B-7. JAWAHAR NAGAR.Main Road ,Kota.
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MASTERING ORGANIC CHEMISTRY
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By-- S.K.SINHA
Disubstituted alkenes may be named in two ways: (i) using terms cis- and trans- or (ii) using terms (E) or (Z). Note: Use of (E) and (Z) stereocenters is preferred. However, the cis-trans terms are accepted.
(E)-pent-2-ene or trans-pent-2-ene (Z)-hex-3-ene or cis-hex-3-ene (b) Triand tetra- substituted alkenes may only be named using the (E-Z) system. 6 1 5
2
4
(c)
(E)-2,3,5-trimethylhex-3-ene
3
Disubstituted cycloalkanes may be named using the terms cis-trans or (R-S). CH3
cis-1-chloro-4-methylcyclohexane (R-S) system not applicable here
Cl
CH3
H
trans-3-methylcyclopentanol (1R,3R)-3-methylcyclopentanol H Chiral carbon atoms are assigned (R) or (S) configuration.
HO
(d)
(S)-5-methylhexan-3-ol H HO
OH H COO
H3 N
(2S,3R)-2-amino-3-hydroxybutanoic acid common name: threonine
H
(e) When both (R-S) and (E-Z) stereodescriptors are present, they are placed in parentheses followed by a hyphen; each stereodescriptor is immediately preceded by its associated number and they are arranged in numerical order. H
OH
Cl
CH3
(3S,4E)-6-methylhept-4-en-3-ol (2Z,4E,6R)-6-chloro-6-methylocta-2,4-diene Step 7 Compounds with multiple bonds and triple bonds have the following suffixes: –adiene, – adiyne, –atriene, –atetraene, and so on. Specify the location of each multiple bond by a locant number placed between the “a” and diene, diyne, triene, etc. (E)-2-ethylhexa-1,4-diene previously: (E)-2-ethyl-1,4-hexadiene Step 8 Compounds with both double and triple bonds are called enynes. Start the numbering of enynes from the end nearest the first multiple bond, regardless of type. When a double bond is the same distance from one end as a triple bond from the other end, assign the double bond the lower number. 6
2
4
2
3
5
7
7
1 1
3
8
6
4 5
(E)-hept-5-en-1-yne (E)-oct-2-en-6-yne Step 9 Write the complete name of the compound as a single word with the correct locant numbers for all substituents, which are listed in alphabetical order. The prefixes di, tri, tetra, etc. do not alter the alphabetical ordering of the substituents. The stereochemistry is indicated by placing the appropriate prefix within parentheses followed by a hyphen in front of the name. Cl 1 6
2 5
(E)-5-chloro-3-methyl-3-en-2-one
3 4 O
O
4-ethyl-2,5-dimethylhexanal (a)
The numbers indicating locations of substituents are separated by commas.
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By-- S.K.SINHA
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The letters and numbers are joined by hyphens. When naming esters, no hyphen is placed between the name of the alkyl group derived from the alcohol and the name of the acid from which the ester was derived. O methyl butanoate O
Step 10 A complex substituent is named by applying the above steps just as if the substituent were a compound itself. We begin numbering the sidechain at the point of attachment to the parent hydrocarbon giving the carbon at the point of attachment the locant of C1. We then give this substituent the suffix –yl. We put this name in parentheses and in front of the parentheses we place the locant number on the parent hydrocarbon. SH
OH Br
2-(bromomethyl)benzenethiol
4
1 3
OH
2
2 3
3-(4-methylcyclohexyl)propane-1,2-diol
1
When a complex sidechain contains a chain that is a ttached to the parent hydrocarbon at a position other than at the end of the chain, the carbon of attachment is still numbered as C1 and the other part of the chain is named as a substituent group to that chain. 1
2 3 4
3
1
4
2
(1-ethylbutyl)benzene 1-(2-ethyl-1-methylbutyl)-2-methylcyclohexane Note: An alternate method of numbering the sidechain is to find the longest chain and begin numbering at the end closest to its attachment to the parent hydrocarbon. The –yl ending is added to the chain parent name and the position of the attachment is placed before the –yl ending. 1 2 3 4
5
1-(3-ethylpentan-2-yl)-2-methylcyclohexane
The table below shows some examples of IUPAC names for commonly known compounds. The IUPAC system allows the trivial names of these compounds to be retained as official IUPAC names and, for some, to be used in naming substituted compounds such as 4-bromobenzoic acid. The IUPAC systematic name for this compound would be 4-bromobenzenecarboxylic acid. OH
IUPAC: Trivial (retained)
N
azabenzene pyridine
1,2-dehydrobenzene benzyne
NH2
benzenol phenol
NH2
NH2
CH3
IUPAC: Trivial (retained)
phenylazane benzenamine aniline O
2-methylphenylazane 2-methylbenzenamine ortho-toluidine
naphthalene-2-ylazane naphthalene-2-amine 2-naphthylamine
O
O
OH
OCH3
IUPAC: Trivial (retained) benzenecarboxylic acid benzoic acid
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1-phenylpropan-1-one propiophenone
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MASTERING ORGANIC CHEMISTRY
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CH3
O
CH
CH2
C
IUPAC: Trivial (retained)
H3C
methylbenzene toluene
CH3
propan-2-one
(ethenyl)benzene styrene
acetone Many other trivial names are also retained but can only be used for the unsubstituted compound. For example, the names butanoic acid (systematic) and butyric acid (trivial retained) are both approved by the 4-bromobutanoic acid and IUPAC. However, BrCH 2CH2CH2COOH must be named systematically as cannot be named as 4-bromobutyric acid.
Hantzsc h-Widman System El ement Val ence Pr ef i x El ement Val ence Si l i con IV Si l a Oxygen II Sul f ur II Thi a Ti n IV Sel eni um I I Sel ena Tel l ur i um I I Boron III Bor a Ni t r ogen III Stems for the Hantzsch-Widman System The stem for six-membered rings depends on the least heteroatom whose name directIy precedes the stem.
Pr ef i x Oxa St anna Tel l ur a Aza Phosphorus I I I
Phospha
preferred heteroatom in the ring i.e., the
To determine the proper stem for six-membered rings, select the set below that contains the least preferred heteroatom before consulting the table.
Ri ng si ze 3 4 5
Unsat urat ed i r ene et e ol e
Sat ur at ed i r ane et ane ol ane
Ri ng si ze 7 8 9
Unsat ur at ed epi ne oci ne oni ne
Sat ur at ed epane ocane onane
Common nomenclature Common nomenclature is an older system of naming organic compounds. Instead of using the prefixes for the carbon skeleton above, another system is used. The pattern can be seen below. Number of carbons
Prefix as in new system
Common name for alkanol
Common name for aldehyde
Common name for acid
1
Meth
-
Formaldehyde
Formic acid
2
Eth
-
Ac etaldehyde
Ac etic acid
3
Prop
-
Propionaldehyde
Propionic acid
4
But
-
Butyr aldehyde
Butyr ic acid
5
Pent
Am yl alcohol
Valer aldehyde
Valer ic acid
6
Hex
-
Caproaldehyde
Caproic acid
7
Hept
Enanthyl alcohol
Enanthaldehyde
Enanthoic acid
8
Oct
Capr yl alcohol
Caprylaldehyde
Caprylic acid
9
Non
-
Pelargonaldehyde
Pelargonic acid
10
Dec
Capr ic alcohol
Capr aldehyde
Capr ic acid
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A. Common Parent Ring Systems 8
1
8
7
2
7
3
6
9
1 2
or 6 5
benzene
4
3 5
naphthalene
10
4
anthracene
B. Monosubstituted Benzenes 1. Most substituents keep their designation, followed by the word “benzene”: Cl NO2 CH2CH3
chlorobenzene
nitrobenzene
ethylbenzene
2. Some common substituents change the root name of the ring. IUPAC accepts these as root names, listed here in decreasing priority: COOH
benzoic acid
SO3H
CHO
benzenebenzaldehyde sulfonic acid
OH
NH 2
phenol
aniline
OCH3
anisole
CH3
toluene
C. Disubstituted Benzenes 1. Designation of substitution—only three possibilities: X X
X
Y Y common: IUPAC:
ortho1,2-
Y para1,4-
meta1,3-
2. Naming disubstituted benzenes—Priorities determine root name and substituents Br COOH HO NH2
OCH3
Br CHO 3-aminobenzoic acid 1,4-dibromobenzene 2-methoxybenzaldehyde
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D. Polysubstituted Benzenes CH3 Cl HN
O2N
COOCH2CH3 NO2
Cl
OH
CH3 3,4-dichloro- N -methylaniline
NO2
NH2
2,4,6-trinitrotoluene (TNT)
ethyl 4-amino-3-hydroxybenzoate
E. Aromatic Ketones A special group of aromatic compounds are ketones where the carbonyl is attached to at least one benzene ring. Such compounds are named as “phenones”, the prefix depending on the size and nature of the group on the other side of the carbonyl. These are the common examples: O O C CH3 acetophenone
C CH2CH3 propiophenone
O
O
C CH2CH2CH3
C
butyrophenone
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Characteristics of organic compo unds
•
Homolog ous series Compounds with the same functional group, differing only in the number of CH2 units in their skeleton are said to be in the same homologous series. They are part of the same family of compounds with similar reactions and characteristics that differ only in the number of carbon atoms that make up the chain. Members of a series will have formula that are linked by a general formula. For example, all alkanes have the general formula CnH2n+2. All organic compounds have six identifying characteristics each. 1. Molecular formula - showing the actual number of atoms of each element in that compound. E.g. C2H4O2 for ethanoic acid, meaning there are two carbon atoms, four hydrogen atoms and two oxygen atoms. 2. Empirical formula - the simplest whole number ratio of the atoms of each element in that compound. E.g. CH2O for ethanoic acid, meaning there is a ratio of 1:2:1 of C:H:O atoms. 3. Structural formula - showing how those atoms are arranged. E.g. CH3CO2H for ethanoic acid, meaning three hydrogen atoms are attached to one carbon atom, which in turn is attached to another carbon atom, which in turn has two oxygen atoms attached to it, one of which has a hydrogen atom attached to it. 4. Graphical formula - showing how these atoms are arranged in space and the bonds between them. Lines represent covalent bonds (shared pairs of electrons) between atoms. E.g. for ethanoic acid, where = represents a double covalent bond and – represents a single covalent bond. H H
C
O
H
C O
H
5. Skeletal formula – showing an abbreviated form of the carbon chain, with each line segment understood to have a carbon atom at each end. These structures may or may not show terminal (end of chain) carbons. E.g. for ethanoic acid O
O OH
Or
H3C
OH
6. Name - based upon an accepted system for naming compounds (IUPAC nomenclature). E.g. CH3CO2H, is called ethanoic acid.
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AL KANES 1. Name the following com pound s i) CH3C(CH3)2CH2CH3
ii) CH3CH2C(C2H5)2CH2CH2CH3 iii) CH3CH(CH3)CH2CH(CH3)CH3 iv) CH3CH2CH(CH3)CH(C2H5)CH2C(CH3)2CH3 2. Draw graphical formula for the following c ompoun ds i) ii) iii) iv) v)
2-methylpropane 3-methylheptane 2,3-dimethylbutane 2,2,6-trimethyloctane 1,3-diethylcyclobutane
AL KENES & AL KYNES 3. Name the following com pound s i) ii) iii) iv) v)
CH3CH2CH=CH2 CH3C CCH3 CH3CH2CH(CH3)C CCH3 CH3C CCH(CH 3)2 CH2=CHCH=CH 2 ≡
≡
≡
4. Draw graphical formula for the following c ompound s i) ii) iii) iv) v)
2,3-dimethylbut-2-ene 4-methylhex-1-yne 3,4-diethylhex-2-ene 4-ethylcyclohex-1-ene 4-ethylcyclohex-1-ene HAL OGEN COMPOUNDS
5. Name the following com pound s i) CH3CH2CH2CH2CH2I
Br O
ii) iii)
(CH 3)2CHBr
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6. Draw graphical formula for the following c ompoun ds i) 2-iodo-2-methylpentane ii) 1-chloro-1-bromoethane iii) triiodomethane iv) 1-bromo-3-chloro-4-methylhexane AL COHOLS 7. Name the following co mpound s i) CH3CH2CH(OH)CH 2CH3 ii) CH3C(CH3)(OH)CH 2CH3 iii) CH3CH(OH)CHBrCH 3 8. Draw graphical formula for the following c ompoun ds i) pentan-2-ol ii) 3-methylhexan-1-ol iii) cyclohexane-1,3-diol AL DEHYDES & KETONES 9. Name the following com pound s i) CH3CH2CH2CHO ii) CH3CH(CH3)COCH3 iii) CH3CH(CH3)CHO iv) CH3CH(CH3)COCH3 10. Draw graphical formula for the followi ng comp ounds i) cyclohexanone ii) 3-methylbutanal iii) 2,2-dimethylpropanal iv) 3-chlorobutan-2-one CARBOXYLIC ACIDS & DERIVATIVES 11. Name the following co mpound s i) CH3CH2CO2H ii) CH3CH2CH(OH)CH 2COOH iii) (CH3)3CCO2H H3C Cl
iv)
H3C
O
12. Draw graphical formula for the followi ng comp ounds i) pentanoic acid ii) 3-aminopropanoic acid iii) butenedioic acid iv) chloro ethanoic acid v) methylpropanoate NITROGEN COMPOUNDS 13. Name the following co mpound s i) CH3CH2CN ii) (C2H5)3N 14. Draw graphical formula for the followi ng comp ounds i) 2-methylbutanonitrile ii)
3-aminopentane
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Name the following compounds according to IUPAC rules:
1
2
3
Br
6
5
4
Cl
8
7
9 Br
Cl
10
11
12 Br
Cl
Answer Key: Alkane Nomenclature 1. 2,3-dimethyl-5-propylnonane 2. 4-bromo-2,2,7,8-tetramethylnonane 3. 3-ethyl-2,4,6,7-tetramethylnonane 4. 2,3-dimethyl-6-[1,2-dimethylpropyl]decane 5. 2,7-dimethyl-5-[1,1-dimethylpropyl]nonane 6. 1-isopropyl-4-methyl-2-propylcyclohexane 7. 1-chloro-1-cyclopentyl-4,4-dimethylheptane 8. 7-bromo—3-cyclopropyl-6-ethyl-2,6-dimethylnonane 9. 3-chloro-1,1-dimethylcyclopentane 10. cis-1-isopropyl-3-methylcyclohexane 11. 2-bromo-4-sec-butyl-1,7-dimethylcyclodecane 12. 1-chloro-2-isopropyl-1,5-dimethylcyclooctane
Aldehydes and Ketones: Nomenclature Problems: Name the following according to IUPAC rules.
O
1.
O
2.
H
H
O 3.
4.
O
OH O 5.
6.
O
HO
H O
O O 7.
8.
OH
O
H
O 9.
10. O
O
O
11.
12.
O
OH 13.
14. O
Br
O
O
H
Aldehydes and Ketones: Nomenclature Answers 1. 4-ethyl-5-methyloctanal 2. 3-n-butyloctanal (or 3-butyloctanal) 3. 6-isopropyl-7-decen-5-one 4. 6-hydroxy-5-methyl-2-hexanone 5. 2,7-octanedione 6. 9-hydroxy-6-oxononanal 7. 3-pentylcyclohexanone 8. 7-hydroxy-3-octenal 9. 4-[2,2-dimethylpropyl]cyclohexanone 10. 1,3-cyclohexanedione 11. 3-[3-hydroxypentyl]cyclohexanone 12. 1-cyclopentyl-2-hexanone 13. 2-[3-oxobutyl]cyclopentanone 14. 2-[1-bromopropyl]hexanal
. : 1.1
Give the IUPAC name of each of the compounds shown. a) CH3 CH2 CH2 CH2 CH3
c) CH3 CH2CHCH 3 | OH
d) CH3 CH2 CHCH 2 CH3 | CH3
e) (CH3 )2 CHCHBrCH 2 CH3
f) (C2H 5 )2 CH(CH 2 )2 CH3
g)
h) CH3 CBr2 CH2CCl3
i) CH3CH2CHCH 2 CH2 CH3 | CH2 OH
j) (CH3 )2 CHCH 2 CH2C=CH 2 | CH3
k)
l) CH3 CH2 C Br 1.2
b) CHCl3
Br
CH3 CH3 | | CH3 CH2 CHCH 2 CHCHCH 3 | CH2 CH2 CH3
CH3 | CH3CH2 C-C C-CH(CH 3 )2 | CH3 ≡
m) CH 3 CH2
C
C H
CH3 CH2
H C H
Draw the structure of each of the compounds named below. a) 2,2-dimethylbutane
b) 3,3-dimethyl-1-butanol
c) 4-ethyl-2,2-dimethylhexane
d) 1,2-dibromo-2-methylpropane
e) 4-methyl-2-pentyne
f)
cis-1-bromo-2-pentene
2.1
Give the IUPAC name of each of the compounds shown. a)
b) (CH 3 )2 CH
CH3
c)
d) Cl
Cl
OH
2.2
3.1
Draw the structure of each of the compounds named. a) 1,3-dimethylcyclobutane b) 4-neopentylcyclohexanol
c) 4-isopropylcyclohexene
Give the name of each of the compounds shown. CH3 a)
b)
c) Cl
d) CH3
3.2
Draw the structure of each of these compounds. a) bicyclo[2.2.0]hexane b) 2-isopropylbicyclo[1.1.0]butane c) 1,5-diethylbicyclo[3.3.0]octane
4.1
Give the common name of each of the compounds shown. a) CH3 CH2 OH b) CH3 CH2 CH2 Cl c) (CH3 )3C-CH 2 OH
d) FC(CH3)3
Draw the structure of each of the compounds named. a) methyl iodide b) isobutyl alcohol c) isopropyl alcohol
d)
4.2
5.1
sec-butyl
Give the common name of each of the following compounds. Br
OH a)
OH
b)
c)
5.2
Draw the structures of the following compounds. a) cyclopropyl chloride b) cyclohexyl iodide
6.
Draw the structures of each of the following compounds. a) propylene b) acetylene c) ethylacetylene
d) ethylene
bromide
SOLUTIONS TO SAMPLE PROBLEMS: 1.1
a) pentane b) trichloromethane c) 2-butanol d) 3-methylpentane e) 3-bromo-2-methylpentane f) 3-ethylhexane g) 5-isopropyl-3-methyloctane h) 3,3-dibromo-1,1,1-trichlorobutane i) 2-ethyl-1-pentanol j) 2,5-dimethyl-1-hexene k) 2,5,5-trimethyl-3-heptyne l) trans-1,2-dibromo-1-butene m) 2-ethyl-1-butene
1.2
a) 2,2-dimethylbutane CH3 | CH3 CCH2 CH3 | CH3
b) 3,3-dimethyl-1-butanol CH3 | HOCH 2 CH2 CCH3 | CH3
c) 4-ethyl-2,2-dimethylhexane CH 3 |
d) 1,2-dibromo-2-methylpropane
CH 2 CH 3
CH3
|
|
CH 3 CCH2 CHCH 2 CH 3 | CH 3
e) 4-methyl-2-pentyne
CH 2 CCH 3 | | Br Br
f)
cis-1-bromo-2-pentene
BrCH 2
CH3 C CCHCH 3 | CH3 ≡
C
CH2 CH3 C H
H 2.1
a) cycloheptane c) 2-methylcyclobutanol
2.2
a) 1,3-dimethylcyclobutane b) 4-neopentylcyclohexanol c) 4-isopropylcyclohexene
CH3
CH3
b) isopropylcyclopentane d) 1,4-dichlorocyclohexene
HO
3.1
a) bicyclo[4.3.0]nonane c) 7-chlorobicyclo[4.1.1]octane
3.2
The structures are:
CH3 | CH2 C-CH 3 | CH3 b) bicyclo[3.2.1]octane d) 1,6-dimethylbicyclo[3.2.0]heptane
CH2 CH3 a)
b)
CH(CH 3 )2
c) CH2CH3
4.1
a) ethyl alcohol
4.2
a) methyl iodide
b) propyl chloride c) neopentyl alcohol d) b) isobutyl alcohol
CH3 I
(CH 3 )2 CHCH 2 OH
5.1
a) cyclopentyl alcohol
5.2
a) cyclopropyl chloride
a) propylene CH3 CH=CH 2
(CH 3)2 CHOH
b) cyclohexyl alcohol
d)
sec-butyl
c) cyclobutyl bromide
I
b) acetylene H-C C-H ≡
c) ethylacetylene CH3 CH2 C C-H ≡
23
bromide
CH 3 CHBrCH 2 CH3
b) cyclohexyl iodide
Cl
6.
c) isopropyl alcohol
tert -butyl fluoride
d) ethylene H 2C=CH 2
