Identify the type of isomer for (R)-3-bromoheptane. O Has to be experimentally determined Dextrorotatory isomer (+) O Levorotatory isomer (-) O Racemic (*)

There are four dimethylcyclopropane isomers. (a) Write three-dimensional formulas for these isomers. (b) Which of the isomers are chiral? (c) If a mixture consisting of 1 mol of each of these isomers were subjected to simple gas chromatography, how many fractions would be obtained and which compounds would each fraction contain? (d) How many of these fractions would be optically active? tod o ors brie page 10 of 17

Draw a structural formula for 2-cyclopenten-1-ol. • Show stereochemistry only if given in the name. • If a group is achiral, do not use wedged or hashed bonds on it. • In cases where there is more than one answer, just draw one.

Draw the following molecule, don't forget stereochemistry : (E)-5-ethyl-5-methylhept-3-ene

Draw a structural formula for 2-methylbutan-2-ol. • You do not have to consider stereochemistry. **** Sn [F ? ChemDoodleⓇ

4. Draw all possible stereoisomers of the following compounds. Assign the appropriate absolute (R/S) or geometric (E/Z) configuration to each of the stereoisomers (or double bonds) and label pairs enantiomers, diastereomers and meso compounds. (a) CH3CHBRCHOHCH3 (c) CH3CH=C(Br)CH=CHCI (e) CH3CH₂CHOHCHOHCH2CH3 (g) OH НО... CI (h) H3C Br (b) CH3CHBRCHBRCH ₂Br (d) CH3CH(C6H5)CHOHCH3 (f) CH₂(OH)CH2-CH(OH)CH=CHOH CH3 (1) Br HS Br

Consider the reaction between (1S,3S)‑1‑chloro‑3‑methylcyclopentane and methanethiol in the presence of sodium hydroxide. (a) Draw the organic product and clearly indicate stereochemistry by showing the hydrogen on the chirality centers and using wedge and dash bonds. (b) Then analyze the stereochemistry of the product. racemic chiral achiral (1R, 3S) (1R, 3R) (1S, 3S)

See attached photo.