The first step of the addition of a hydrogen halide to an alkene is the addition of H+ to an sp² carbon to form a carbocation. Predict t carbocation formed in the following reaction and draw the mechanism of its formation. Edit the reaction by drawing all steps in the appropriate boxes and connecting them with reaction arrows. Add charges where needed. Electron-flow arrows should start on an atom or a bond and should end on an atom, bond, or location where a new bond should be created. DCQQ H ©\\\\\²2²0 +²√² سهند bul H с N 0 S

Consider this organic reaction: Draw the major products of the reaction in the drawing area below. If there won't be any major products, because this reaction won't happen at a significant rate, check the box under the drawing area instead. CI No Reaction. Click and drag to start drawing a structure. A : ☐

Draw the organic product structure formed by the reaction sequence. Draw the product. Select Draw Rings More Erase H 1. B2H6, diglyme 2. NaOH, H,O, Н-О2

Hydroboration of Alkenes vs. Alkynes. Addition of an alkylboranes to a carbon- carbon double bond ("hydroboration") followed by oxidation is a common way to alcohols, for example, addition of dimethylborane to 2,3-dimethyl-2-butene yields 2,3-dimethyl-2-butanol. Me₂BH + Me₂C=CMe₂- →→ Me₂CH-CMe₂OH The reaction is more general as borane also adds to carbon-carbon triple bonds. obtain structures and energies for reactants and transition states for addition of dimethylborane (Me₂BH) to both ethylene and acetylene. Which reaction has the lower activation energy? Offer an explanation for your result.

For the reaction scheme below, label each reactant (identified as 'reactant 1-4') as either a nucleophile (Nu) or electrophile (E). Use the box labeled for each reactant for your answer. You only need to write Nu or E for your answer. H-Bri Ta -Br: reactant 1 reactant 2 reactant 3 Reactant 1: Reactant 2: Reactant 3: Reactant 4: Br: reactant 4

CH=CHCN 3-phenylpropenenitrile Electrophilic substitution on 3-phenylpropenenitrile occurs at the meta position. Draw resonance structures to show how the ring is electron-poor at the ortho and para positions. ● • You do not have to consider stereochemistry. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate resonance structures using the → symbol from the drop-down menu.

Draw a structural formula for the substitution product of the reaction shown below. Br H NH3 CH₂OH • Use the wedge/hash bond tools to indicate stereochemistry where it exists. If more than one stereoisomer of product is formed, draw both. • Separate multiple products using the + sign from the drop-down menu. • Products that are initially formed as ions should be drawn in their neutral forms.

Draw structural formulas for organic products A and B in the window below. ● ● ● -CH₂CI Li pentane Cul ChemDoodleⓇ Draw only products having the organic portion of the original alkyl halide. Draw carbon-lithium bonds using the single bond tool. If a structure has a copper-lithium bond, do not draw the lithium. Separate products from different steps using the → sign from the drop-down menu. B Sn [F

3. Use curved arrows to show electron movement in the reactant side and draw the product/s of the Lewis (nucleophile-electrophile) reaction. Draw in all lone pairs and charges where appropriate. acid-base -co +

Alcohols can be converted to alkyl bromides using PBr3, which causes a complete inversion of stereochemistry. OH 10 PBr 3 Draw the stepwise mechanism for bromination of an alcohol. Be sure to include non-zero formal charges and lone pairs as necessary. : OH Br of 0 Br. Br Br Add/Remove step X Click and drag to st= drawing a structur