5. Chirality

Identify the following molecules as chiral or achiral. If chiral, draw the nonsuperimposable mirror image and verify its nonsuperimposability.

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Which of the following objects are chiral?

a. a mug with DAD written to one side of the handle

b. a mug with MOM written to one side of the handle

c. a mug with DAD written opposite the handle

d. a mug with MOM written opposite the handle

Which of the following objects are chiral?

e. a wheelbarrow

f. a remote control device

g. a nail

h. screw

Draw structures for the following:

d. a chiral stereoisomer of 1,2-dibromocyclobutane

Draw structures for the following:

e. two achiral stereoisomers of 3,4,5-trimethylheptane

For each compound, determine whether the molecule has an internal mirror plane of symmetry.

If it does, draw the mirror plane on a three-dimensional drawing of the molecule.

If the molecule does not have an internal mirror plane, determine whether the structure is chiral.

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(•) Classify the following objects and molecules as chiral or achiral.

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Identify all planes of symmetry in the following molecules/conformations, if any.

(d) <IMAGE>