MCAT Organic Chemistry Review 2018-2019

Chapter Profile The content in this chapter should be relevant to about 7% of all questions about Organic Ch ...

on describing the carboxylic acid derivatives that appear on the MCAT: amides, esters, and anhydrides. Each of ...

9.1 Amides, Esters, and Anhydrides LEARNING GOALS After Chapter 9.1, you will be able to: Apply the rules for ...

Amides Amides are compounds with the general formula RCONR 2 . They are named by replacing the –oic acid suff ...

Amides may or may not participate in hydrogen bonding depending on the number of alkyl groups they have bonde ...

Cyclic esters are called lactones and are named in the same manner as lactams, with the name of the precu ...

condensation or dehydration of diacids; their structures need not be memorized, but recognize them as cyclic ...

Figure 9.8. Synthesis of an Anhydride via Carboxylic Acid Condensation Two molecules of carboxylic acid come ...

Anhydrides often have higher boiling points than their related carboxylic acids, based solely on their much ...

9.2 Reactivity Principles LEARNING GOALS After Chapter 9.2, you will be able to: Order carboxylic acid deri ...

When considering the reactivity of carboxylic acid derivatives toward nucleophilic attack, anhydrides are the most ...

effect is relatively weak and gets increasingly weaker as one moves further away within the molecule from ...

KEY CONCEPT Induction is the distribution of charge across σ bonds. Conjugation and resonance are much more pow ...

β-lactam rings, as a resistance mechanism against these antibiotics. Therefore, β-lactams are sometimes give ...

9.3 Nucleophilic Acyl Substitution Reactions LEARNING GOALS After Chapter 9.3, you will be able to: Descr ...

substitution reaction, but also a cleavage reaction because it splits an anhydride in two. In this rea ...

Figure 9.15. Nucleophilic Acyl Substitution: Anhydride to Carboxylic Acids TRANSESTERIFICATION Alcohols can act as ...

Figure 9.17. Nucleophilic Acyl Substitution: Amide to Carboxylic Acid Strong acid or base is needed to cat ...

How do strongly acidic and strongly basic conditions catalyze the hydrolysis of an amide? Strongly acidic c ...

Conclusion We’re sure you’ve noticed that this chapter covers only a few reactions happening in a wide ...