Reagents+predict the product

Predict the product: an alkene+Cl2+hv(light)

Replaces a hydrogen bond with a chlorine bond

Reagent(s) needed to polymerize an alkene

Benzoyl peroxide and heat

Predict the product(write it out twin)

Predict the product(write it out twin)

Predict the product(write it out twin)

Predict the product: an alkene + NBS + hv

Bromine bond replaces an allylic hydrogen

What are two reagent combinations to brominate a molecule at an allylic, benzylic, or propargylic hydrogen position?

NBS+ hv; NBS+ benzoyl peroxide+ heat

What reagent(s) could you use to replace alcohol with chlorine with retention of stereochemistry?

SOCl2

What reagent(s) could you use to replace alcohol with chlorine with inversion of stereochemistry?

SOCl2 and pyridine

Predict the products(2 of them)

What reagents are used to create an organolithium?

An organohalide + 2 Li(s)

Predict the product:

What reagents are required to replace the bromine in 1-bromohexane with hydrogen?

Mg(s), then water

What reagent is required to bromobenzene to phenyllithium?

2Li(s)

2RLi + ____ = gilman reagent

CuX X=I, Cl, or Br

____ + CuX = Normant reagent

2RMgX

What is the product of an organohalide+ R₂CuLi?

The halogen on the organohalide will be replaced with R

What is the product of an organohalide+ R₂CuMgX?

The halogen on the organohalide will be replaced with R

Reagents for adding a halogen to benzene:

X2 + Fe(0)+ heat OR FeBr3(or any lewis acid)

Reagents for adding a NO2 to benzene:

HNO3(nitric acid) + H2SO4

Reagents for adding HSO3 to benzene:

SO3 + H2SO4

Reagents for removing HSO3 from benzene

H2SO4 and water

Reagents for adding an alkyl group to benzene:

AlCl3 and the alkyl group of interest

Reagents for adding an acyl group to benzene:

Acyl chloride + AlCl3

Reagents for clemmenson reduction:

Zn(Hg)+ HCl

Reagents for Wolff-Kishner reduction

H2N-NH2 + KOH

What does cross coupling an organohalide with a gilman/normant reagent produce?

Replaces the halide with the R group of the reagent

what does reacting this compound with 2Li(0) and D2O give?

Possible reagents for chlorination of benzene

NCS or Cl-Cl + FeCl3

Possible reagents for iodization of benzene

NIS or Acetyl hypoiodite

What reaction and reagent can be used to replace the leaving group on the molecule pictured with alcohol?

SNAr reaction, NaOH

Predict the product if these two reagents are reacted with heat.

Remember not to draw an extra hydrogen on N.

What solvent can be used so that these two reagents undergo a SNAr reaction?

NaHCO3, or any weak base

What reagents are needed in “SNAr“ reactions with benzyne intermediates?

NaNH2(sodium amide) and liquid NH3(ammonia)

What metals dissolve in liquid ammonia to give a soup of electrons?

Na(s) and Li(s)

Predict the product

Predict the product

I think this

Predict the major and minor product

Name the reagent and predict the product

TsCl=tosyl chloride

What reagents are used for acid catalyzed hydration of alkenes?

H2SO4(or any strong acid), H2O

Is acid catalyzed hydration of alkenes mark or antimark? What is its stereochemistry?

Mark. Stereochem is not applicable, will result in a mixture.

Predict the product

What reagents are needed for oxymercuration demercuration?

1. Hg(OAc)2, H2O

2. NaBH4, NaOH

Is oxymercuration demercuration mark or anti mark? What is its stereochemistry?

Mark, anti addition

Predict the product.

Is hydroboration oxidation mark or anti mark? What is its stereochemistry?

Antimark, syn addition

What reagents are needed for hydroboration oxidation?

1. BH3 THF

2. NaOH, H2O2

Predict the product

What reagent is used to form a symmetric ether out of identical alcohols?

Catalytic amounts of H2SO4 or HCl

Predict the product

What reagents can be used to form a ring?

NaOH, H2O

Predict the product

Predict the product

Note the inversion of the H and CH3. Nitrogen only has 2 hydrogens that makes it neutral.

What starting mats and reagents are needed to form this product?

EtOH

Predict the product

Too hindered for SN2, E2 instead

Predict the product