Show all possible constitutional isomers of C₅H₁₂O. Label them as functional, positional, or chain isomers.

Convert the following structural formulas to line-angle drawings

(c) CH₃CH₂NHCH₂CH₂OH

Predict the shape and hybridization of the indicated atoms.

What type of isomerism is indicated by each of the following pairs of molecules? Be as specific as possible.

(a)

What type of isomerism is indicated by each of the following pairs of molecules? Be as specific as possible.

(b)

What type of isomerism is indicated by each of the following pairs of molecules? Be as specific as possible.

(d)

What type of isomerism is indicated by each of the following pairs of molecules? Be as specific as possible.

(e)

The molecule A undergoes a three-step reaction to make B, where the first step is rate determining. Conversely, C can be produced by A in a two-step reaction where the second step is rate determining. Show a reaction coordinate diagram for each reaction, making it clear that the reaction to make C is faster than the reaction to make B.

In Chapters 8 and 17 we learn two reactions for the synthesis of the alcohol shown. (a) Show a mechanism for each of the reactions. (b) If you were designing a synthetic route, which would be considered more sustainable? Consider all factors. [Assume the starting organic molecules are equally green.]

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

(a)

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

(c)

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

(d)

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

(f)

For each of the following molecules, draw a 3-D representation.

(c) CHBr₃

For each of the following molecules, draw a 3-D representation.

(d) CHClBrI

For each of the following molecules, draw one 3-D representation at only the necessary atoms (that is, the ones with four different atoms/groups attached).

(a)

For each of the following molecules, draw one 3-D representation at only the necessary atoms (that is, the ones with four different atoms/groups attached).

(b)

For each of the following molecules, draw one 3-D representation at only the necessary atoms (that is, the ones with four different atoms/groups attached).

(c)

For each of the following molecules, identify all stereocenters and draw all possible stereoisomers.

(a)

For each of the following molecules, identify all stereocenters and draw all possible stereoisomers.

(b)

For each of the following molecules, identify all stereocenters and draw all possible stereoisomers.

(e)

For each of the following molecules, identify all stereocenters and draw all possible stereoisomers.

(f)

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

(c)

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

(e)

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

(f)

A molecule of the type shown is discussed in greater detail in Section 6.5.1. Although it contains at least one atom with four different groups attached, why is it not a chiral molecule?

For each of the following chiral molecules, obtain the enantiomer (i) by drawing the nonsuperimposable mirror image and (ii) by switching the spatial orientation at each asymmetric center. Confirm (possibly using models) that the structures you drew for (i) and (ii) are the same.

(b)

For each of the following chiral molecules, obtain the enantiomer (i) by drawing the nonsuperimposable mirror image and (ii) by switching the spatial orientation at each asymmetric center. Confirm (possibly using models) that the structures you drew for (i) and (ii) are the same.

(d)

Draw the mirror image of the following molecule. Then, using the mirror image generated, switch the spatial orientation at the asymmetric center. Is the final structure the enantiomer of the original? If not, what is it?

A molecule of the type shown here is discussed in greater detail in Section 6.5.1. Draw the mirror image. Is it superimposable? Switch the spatial orientation at both asymmetric centers. Have you generated a new molecule?