Draw structures for the carbonyl electrophile and enolate nucleophile that react to give the aldol or enone below. (One of many steps in a synthesis of ẞ-carotene) • Consider E/Z stereochemistry of alkenes. • Draw the enolate ion in its carbanion form. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate multiple reactants using the + sign from the drop-down menu.

For each reaction, decide whether the reaction is a redox reaction, acid-base reaction, electrophile- nucleophile, or something else. One can begin to identify the type of reaction by looking to see if oxidation numbers of atoms that take part in the reaction change during the reaction. You will need to draw out the structures. a. If the reaction is considered an acid- base reaction, draw out the full mechanism for the reaction. Be sure to indicate which compound is the acid, base, and conjugate acid and base (where possible). b. If the reaction is considered a redox reaction, be sure to indicate which species are oxidized and which are reduced. c. For every reaction you will need to justify your identification of the type of reaction.

[Review Topics] [References] Draw structural formulas for an aldehyde or ketone and alkyl (or aryl) bromide that could be used in a Grignard synthesis of the alcohol shown. • You do not have to consider stereochemistry. If there is more than one combination, draw only one. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate multiple reactants using the + sign from the drop-down menu. . CH3 CH3CHCH₂-OH + H... 9 ChemDoodle

This experiment is aldol condensation reaction. Complete the table