100% satisfaction guarantee Immediately available after payment Both online and in PDF No strings attached
logo-home
Previously searched by you
Previously searched by you
logo
Orgo McMurry Ch. 11 Actual Questions And Answers Verified. CA$18.85   Add to cart
Quickly navigate to
Preview
  2.  
  3. MCMURRY
  4.  
  5. MCMURRY

Exam (elaborations)

Orgo McMurry Ch. 11 Actual Questions And Answers Verified.
 8 views  0 purchase
  • Course
  • MCMURRY
  • Institution
  • MCMURRY

Alkyl halides do one of two things when they react with a nucleophile/base, such as a hydroxide ion... - correct answer (1) undergo SUBSTITUTION of the X group by the nucleophile OR (2) undergo ELIMINATION of HX to yield an alkene carbon-halogen bonds in al...

[Show more]

Preview 2 out of 7  pages

Document information

  • October 9, 2024
  • 7
  • 2024/2025
  • Exam (elaborations)
  • Questions & answers

Subjects

  • orgo mcmurry ch 11

Written for

  • MCMURRY
  • MCMURRY

Seller

avatar-seller
RealGrades

Reviews received

Content preview

Orgo McMurry Ch. 11

Alkyl halides do one of two things when they react with a nucleophile/base, such as a hydroxide ion... -
correct answer (1) undergo SUBSTITUTION of the X group by the nucleophile

OR

(2) undergo ELIMINATION of HX to yield an alkene



carbon-halogen bonds in alkyl halides are polar and the carbon atoms are electron-poor, thus, alkyl
halides are ELECTROPHILES



Nucleophilic Substitution Reactions - correct answer -each step involves the
substitution of one nucleophile (Cl- or OH-) by another

-one of the most common and versatile reaction types in organic chemistry



Alkyl P-Toluenesulfonate - correct answer = a tosylate (Tos)



Note:

-for practical purposes, the ENTIRE tosylate group acts as if it were simply a halogen substituent

-when you see a tosylate substituent in a molecule, tell yourself that you're dealing with an alkyl halide!



Second-Order Reaction - correct answer = a reaction in which the rate is linearly
dependent on the concentrations of two species



Rate Equation (of second-order rxn) - correct answer = expression of the second-
order dependence of the nucleophilic substituion reaction

-you can see, as either [RX] or [-OH] changes, the rate of the reaction changes PROPORTIONATELY



SN2 Reaction - correct answer short for: substitution, nucleophilic, bimolecular

, -the essential feature of the SN2 mechanism is that it takes place in a SINGLE step without intermediates
when the incoming nucleophile reacts with the alkyl halide or tosylate (the SUBSTRATE) from a direction
180 degrees opposite the group that is displaced (the LEAVING GROUP); resulting in an umbrella-like
inversion of configuration at the carbon atom

-as the nucleophile comes in on one side of the substrate and bonds to the carbon, the halide or tosylate
departs from the other side, thereby INVERTING the stereochemical configuration

-the reaction is kinetically SECOND-ORDER and is strongly inhibitied by increasing steric bulk of the
reactants

-SN2 reactions are favored for PRIMARY and SECONDARY substrates



Bimolecular - correct answer ...means two molecules, nucleophile and alkyl halide,
take part in the step whose kinetics are measured (rate-determining step=RDS)



Illustrated SN2 Mechanism - correct answer Reaction of (S)-2-bromobutane with
HO- to give (R)-2-butanol:

-the SN2 reaction occurs when an electron pair on the nucleophile Nu- forces out the group X:-, which
takes with it the electron pair from the former C-X bond (happens thru a ts)



Transition State of SN2 - correct answer -the new Nu-C bond is partially forming at
the SAME time that the old C-X bond is partially breaking and in which the negative charge is SHARED by
both the incoming nucleophile and the outgoing halide ion

-the ts for this inversion has the remaining three bonds to carbon in a PLANAR arrangement



Effects of Changes in Reactant and ts Energy Levels on Rate - correct answer (a) a
higher reactant energy level (red) corresponds to a FASTER reaction (smaller Ea)

(b) a higher transition-state level (red) corresponds to a SLOWER reaction (larger Ea)

Note: some SN2 rxn are fast and some are slow; can take place in high or low yield



SN2 Reactivity - correct answer



Energy Diagrams: Effects on SN2 Rxn - correct answer Graphs display effects of:

(a) Substrate

(b) Nucleophile

The benefits of buying summaries with Stuvia:

Guaranteed quality through customer reviews

Guaranteed quality through customer reviews

Stuvia customers have reviewed more than 700,000 summaries. This how you know that you are buying the best documents.

Quick and easy check-out

Quick and easy check-out

You can quickly pay through credit card or Stuvia-credit for the summaries. There is no membership needed.

Focus on what matters

Focus on what matters

Your fellow students write the study notes themselves, which is why the documents are always reliable and up-to-date. This ensures you quickly get to the core!

Frequently asked questions

What do I get when I buy this document?

You get a PDF, available immediately after your purchase. The purchased document is accessible anytime, anywhere and indefinitely through your profile.

Satisfaction guarantee: how does it work?

Our satisfaction guarantee ensures that you always find a study document that suits you well. You fill out a form, and our customer service team takes care of the rest.

Who am I buying these notes from?

Stuvia is a marketplace, so you are not buying this document from us, but from seller RealGrades. Stuvia facilitates payment to the seller.

Will I be stuck with a subscription?

No, you only buy these notes for CA$18.85. You're not tied to anything after your purchase.

Can Stuvia be trusted?

4.6 stars on Google & Trustpilot (+1000 reviews)

75632 documents were sold in the last 30 days

Founded in 2010, the go-to place to buy study notes for 14 years now

Start selling
CA$18.85
  • (0)
  Add to cart