# IM14. Solutions to problems

##### Problem IM7.4.

a) bromide    b) oxide    c) fluoride    d) carbonate    e) nitrate    f) nitrite

g)  sulfide    h) sulfate    i) sulfite    j) persulfate    k) carbide    l) nitride     m) arsenide

n) phosphate    o) phosphite    p) iodide    q) iodate    r)  periodate

##### Problem IM8.2.

a)  (CH3)2CHCH2CH2CN        b)  CH3CH2CH(OH)CH3

c)  (CH3)2CHCOCH2CH3        d)  CH3CH2CONHCH2CH3

a)  octahedral.

b)

c)

##### Problem 10.2.

a) trigonal bipyramidal

b)  This time there could be two different answers.

If the lone pair occupies one of the axial positions, it would be pretty close to three other atoms.

If the lone pairs occupies one of the equatorial positions, it would be pretty close to only two other atoms.  The other equatorial atoms are pretty far away.

The rule is that the lone pair goes in the less crowded position, so this molecule would be see-saw shaped.

c)  Again, there are two possible geometries.  One of them would be trigonal planar, a pretty common geometry.

However, that places the lone pairs in the more crowded positions.   Instead, the molecule is going to be tee shaped.

##### Problem IM10.4.

a) bent        b) pyramidal  at O, although tetrahedral at C      c)  pyramidal

d)  see-saw        e)  tee        f)  trigonal bipyramidal

g)  octahedral        h) square pyramidal            i)  square planar

##### Problem IM12.2.

a) propane        b) pentane        c)  hexane

##### Problem IM12.3.

a)  3-methylhexane        b)  2,2-dimethylpentane        c) 2,3-dimethylbutane

d)  2,2,3,3-tetramethylpentane        e)  3,5-dimethylheptane        f) 4-ethyl-3,6-dimethyloctane

##### Problem IM12.4.

a)  cyclopentane        b)  cyclohexane        c)  cyclooctane

d)  methylcyclobutane        e)  1,1,3-trimethylcyclopentane        f) 1,3-dimethylcycloheptane

##### Problem IM12.5.

a) 1-hexene        b) 2-methyl-2-pentene        c)  1-methylcyclohexene    d)  2,4,6-trimethyl-2-heptene

##### Problem IM12.6.

a) cyclopentene        b) 1,1-dimethylcyclohexane        c)  3-hexyne

d)  4-methylcyclohexene        e)  1-hexyne

##### Problem IM12.7.

a)  tetrahedral        b)  trigonal planar        c) linear

##### Problem IM12.8.

a)  methylbenzene        b) propylbenzene        c) 1,2-dimethylbenzene or o-dimethylbenzene (also o-xylene)

d) 1,3-dimethylbenzene or m-dimethylbenzene (also m-xylene)    e)  1,4-diethylbenzene or p-diethylbenzene

f)  2-ethyl-1,4-dimethylbenzene

##### Problem IM12.9.

a)  2,2-dimethylhexanal    b)  2-methylcyclopentanone

c)  3-nonanone        d)  2,4-dimethyl-2-hexenal

##### Problem IM12.10.

a)  butyl propanoate        b)  N,N-diethylbutanamide

c)  6-methylheptanoic acid            d)  4-pentenoic acid

##### Problem IM12.11.

a)  1-chloro-2-methylcyclohexane        b)  cyclooctanol        c)  ethyl cyclopentyl ether

d)  N-propylcyclohexylamine        e), 5,5-dimethylheptan-2-ol        f)  3-bromo-4,4-dimethyloctane

g)  dibutylamine        i)  methyl phenyl ether (or anisole)        j)  ethane thiol        k)  diethyl thioether

l) triethylphosphine        m) butanenitrile        n)  nitromethane

Note that sometimes a number is located directly in front of the suffix for the group to which it refers.

##### Problem IM12.12
1. benzene (or aromatic), ketone and ether
2. bromide, amine and aldehyde
3. alcohol, thiol and ester
4. thioether, amide and alkene
5. alkyne, alcohol and carboxylic acid